[ CAS No. 572-83-8 ] {[proInfo.proName]}

Name: 572-83-8|2-Bromoanthracene-9,10-dione|98%
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SKU: A212808
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Quality Control of [ 572-83-8 ]

COA NMR CNMR HPLC LC-MS

Related Doc. of [ 572-83-8 ]

SDS Specification

Alternatived Products of [ 572-83-8 ]

Product Details of [ 572-83-8 ]

CAS No. :	572-83-8	MDL No. :	MFCD00474541
Formula :	C₁₄H₇BrO₂	Boiling Point :	-
Linear Structure Formula :	-	InChI Key :	VTSDGYDTWADUJQ-UHFFFAOYSA-N
M.W :	287.11	Pubchem ID :	221013
Synonyms :

Calculated chemistry of [ 572-83-8 ]

Physicochemical Properties

Num. heavy atoms :	17
Num. arom. heavy atoms :	12
Fraction Csp3 :	0.0
Num. rotatable bonds :	0
Num. H-bond acceptors :	2.0
Num. H-bond donors :	0.0
Molar Refractivity :	67.45
TPSA :	34.14 Å²

Pharmacokinetics

GI absorption :	High
BBB permeant :	Yes
P-gp substrate :	No
CYP1A2 inhibitor :	Yes
CYP2C19 inhibitor :	Yes
CYP2C9 inhibitor :	Yes
CYP2D6 inhibitor :	No
CYP3A4 inhibitor :	No
Log Kp (skin permeation) :	-4.73 cm/s

Lipophilicity

Log Po/w (iLOGP) :	2.26
Log Po/w (XLOGP3) :	4.68
Log Po/w (WLOGP) :	3.22
Log Po/w (MLOGP) :	2.51
Log Po/w (SILICOS-IT) :	4.2
Consensus Log Po/w :	3.38

Druglikeness

Lipinski :	0.0
Ghose :	None
Veber :	0.0
Egan :	0.0
Muegge :	0.0
Bioavailability Score :	0.55

Water Solubility

Log S (ESOL) :	-5.09
Solubility :	0.00233 mg/ml ; 0.00000811 mol/l
Class :	Moderately soluble
Log S (Ali) :	-5.12
Solubility :	0.00216 mg/ml ; 0.00000751 mol/l
Class :	Moderately soluble
Log S (SILICOS-IT) :	-6.09
Solubility :	0.000234 mg/ml ; 0.000000815 mol/l
Class :	Poorly soluble

Medicinal Chemistry

PAINS :	1.0 alert
Brenk :	0.0 alert
Leadlikeness :	1.0
Synthetic accessibility :	2.32

Safety of [ 572-83-8 ]

Signal Word:	Warning	Class:	N/A
Precautionary Statements:	P261-P305+P351+P338	UN#:	N/A
Hazard Statements:	H302-H315-H319	Packing Group:	N/A
GHS Pictogram:

Application In Synthesis of [ 572-83-8 ]

* All experimental methods are cited from the reference, please refer to the original source for details. We do not guarantee the accuracy of the content in the reference.

Upstream synthesis route of [ 572-83-8 ]
Downstream synthetic route of [ 572-83-8 ]

[ 572-83-8 ] Synthesis Path-Upstream 1~7

1
[ 572-83-8 ]
[ 613-14-9 ]

Reference： [1] Tetrahedron Letters, 2003, vol. 44, # 6, p. 1215 - 1219

2
[ 572-83-8 ]
[ 7321-27-9 ]

Yield	Reaction Conditions	Operation in experiment
82.02%	Stage #1: at 105℃; for 0.5 h; Stage #2: at 30 - 110℃; for 0.333333 h;	In a preferred embodiment,To a 500 mL three-necked flask was added 275.0 g diglyme,68.0 g (0.51 mol) of aluminum chloride solid was added slowly,The control temperature was 60 ° C,About 20min feeding is completed,The system becomes gray or milky white turbidity.Cooling to 30 ,stand-by.A further 1 L three-necked flask was charged with 49.2 g (0.17 mol) of 2-bromoanthraquinone,200.0 g diglyme,Stir,27.5 g (0.51 mol) of potassium borohydride was added,The system becomes yellow-green turbidity,Heating up to 105 ° C,And heat for 30 minutes,During the heating process, the system changed from yellow-green turbidity to pink turbidity,Finally into brown turbidity.Insulation is completed,The above-mentioned aluminum chloride solution was slowly added to the system,Control the internal temperature between 90 ~ 110 ,Drop before the first 1/3 of the exothermic reaction,After 2/3 of the process, the endothermic reaction,Dripping with the full range of bubbles,System from brown turbidity into bright yellow turbidity,Finally turned into yellow turbidity.The feeding process is about 20 minutes.Feeding is completed,Quickly cool the water bath to 40 ° C.The system was poured into concentrated hydrochloric acid / water / ethanol (100 g / 400 g / 300 g)System exotherm, accompanied by a large amount of gas generated.Hydrolysis process control system temperature below 60 .Hydrolysis is completed, cooling to 25 ,Filter,100.0g of water and 100.0g of anhydrous ethanol were leaching filter cake was yellow filter cake,This product is crude product.According to crude:Anhydrous ethanol = 1: 10 by the addition of absolute ethanol,Heating up to 50 ~ 60 ,Stirring for 1.0 hr,Cooling to 25 ~ 30 ,Insulation 0.5hr, suction filter,A small amount of anhydrous ethanol leaching filter cake was white solid,This is the product quality,Dried (50 ° C, 200 Pa, 5 hr) to give 35.8 g of a white powdery solid,This is the product quality, the yield of 82.02percent
61%	at 150℃; for 96 h;	Compound 1 (2 g, 6.9 mmol), hydroiodic acid (10.6 mL), and hypophosphorous acid (6.4 mL) were dissolved in acetic acid (17 mL). The mixture was stirred for 96 h at 150 °C. The reaction mixture was cooled to room temperature. The precipitate was filtered and washed with ethanol. The solid was purified via soxhlet extraction with toluene, yielding compound 2 as a pure yellow solid. Yield: 1.1 g (61percent). ¹H-NMR (300 MHz, CDCl₃, ppm): δ 8.44-8.41 (t, 1H, J = 6.9 Hz), 8.34-8.30 (d, 2H, J = 10.2 Hz), 8.19-7.99 (q, 2H, J = 3.3 Hz), 7.91-7.87 (d, 1H, J = 6.0 Hz), 7.91-7.73 (dd, 1H, J = 9.0, 9.3 Hz), 7.68-7.49 (m, 2H); ¹³C-NMR (75 MHz, CDCl₃, ppm): δ 133.65, 129.89, 129.83, 129.65, 128.87, 128.23, 128.19, 128.12, 126.58, 126.55, 126.05, 126.00, 125.78, 125.37; EI, MS m/z (percent): 256 (100, M⁺).
48%	With aluminum tri-sec-butoxide In cyclohexanol at 160 - 162℃; for 16 h;	A 1-L, 3-necked flask was fitted with a distillation head and purged with N2. The system was charged with 2-bromoanthraquinone (29.0 g, 101 mmol), cyclohexanol (350 mL), and aluminum tri-sec-butoxide (140 mL, 550 mmol). The mixture was heated and became deep amber as distillate was collected until the pot temperature was 162 °C. The reaction was heated at 160 °C for 16 h and then cooled to room temperature. The mixture was mixed with tetrahydrofuran (100 mL) and poured onto a 2 L filter frit to isolate the black solid. The solid was stirred on the frit with 6 M HCl (100mL) and then further washed with water (500 mL). The gray crude product was air-dried overnight. The solid was purified further by gradient sublimation at a source temperature of 120°C to afford 12.6 g (48percent) of off-white product. DSC data: peak temp 220 °C (ΔH = 126 Jg^-1. IR (KBr, strong abs only): 892,741, 474 cm_-1. H NMR (500 MHz, d&6-Me₂SO, internal TMS). δ 7.56 (m, 6 lines, 6-H, 8-H), 7.60 (dd, J = 2.0, 9.0 Hz, 7-H), 8.09 (M, 1-H, 3-H, 4-H), 8.39 ('d', J = 1 Hz, 9-H), 8.57 (s, 5-H), 8.63 (s, 10-H).

26%

With sodium tetrahydroborate In tetrahydrofuran; isopropyl alcohol at 0 - 20℃; for 15 h;

2-Bromoanthraquinone 10 (8.50 g, 0.0296 mol, 1 equiv) and a 50:50 mixture of isopropyl alcohol and tetrahydrofuran (200 mL) were stirred for 10 minutes at 0° C. forming a yellow suspension. NaBH₄(6.70 g, 0.177 mol, 6.0 equiv.) was added to the suspension at 0° C. The mixture was stirred at 0° C. for three hours, turning red in color. The solution was then warmed to room temperature. Additional NaBH₄(3.35 g, 0.089 mol, 3.0 equiv.) was added to the solution at room temperature and the solution was stirred at room temperature for 12 hours, turning into an orange suspension. Deionized water (10 mL) was added to the solution at room temperature and the solution was stirred at room temperature for an additional 12 hours. The consumption of 2-bromoanthraquinone 10 was monitored by thin-layer chromatography (35percent CHCl₃/hexane, R_f=0.33). Once the consumption of 2-bromoanthraquinone 10 stopped entirely (it was never fully consumed), the volatiles were removed by rotary evaporation. 3 M HCl was slowly added to the solution until bubbling ceased, then additional 3 M HCl (30 mL) was added. The solution was heated at reflux for 6 hours, turning into an opaque, yellow suspension in the process. The mixture was cooled to room temperature, turning into a transparent solution containing yellow-brown crystals. The contents underwent rotary evaporation as much water as possible. The contents were then vacuum-filtered and washed using deionized water to remove any water, acid and ionic salt, leaving behind a yellow-brown colored solid. The vacuum-filtration receiving flask was changed and the solid was washed with CH₂Cl₂through the filter paper. The CH₂Cl₂was removed through rotary evaporation. The remaining solid was purified through column chromatography (100percent hexane, R_f=0.27), providing 2-bromoanthracene 11 as a white, powdery solid (2.00 g, 26percent). ¹H NMR (CDCl₃): δ 8.42 (s, 1H), 8.34 (s, 1H), 8.18 (d, 1H), 8.01 (m, 2H), 7.87 (d, 1H), 7.50 (m, 3H).

Reference： [1] Patent: CN106916049, 2017, A, . Location in patent: Paragraph 0031; 0032; 0033; 0034; 0035; 0036; 0037-0042
[2] Dyes and Pigments, 2015, vol. 120, p. 30 - 36
[3] Bulletin of the Korean Chemical Society, 2012, vol. 33, # 11, p. 3810 - 3816
[4] Journal of Nanoscience and Nanotechnology, 2012, vol. 12, # 5, p. 4269 - 4273
[5] Tetrahedron Letters, 2003, vol. 44, # 6, p. 1215 - 1219
[6] Patent: WO2005/19198, 2005, A1, . Location in patent: Page/Page column 26-27
[7] Patent: US8410311, 2013, B1, . Location in patent: Page/Page column 9

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[ 572-83-8 ]
[ 2269-22-9 ]
[ 7321-27-9 ]

Yield	Reaction Conditions	Operation in experiment
48%	With hydrogenchloride In tetrahydrofuran; cyclohexanol	EXAMPLES Objects and advantages of this invention are further illustrated by the following examples, but the particular materials and amounts thereof recited in these examples, as well as other conditions and details, should not be construed to unduly limit this invention. Synthesis of 2-bromoanthracene A 1-L, 3-necked flask was fitted with a distillation head and purged with N₂. The system was charged with 2-bromoanthraquinone (29.0 g, 101 mmol), cyclohexanol (350 mL), and aluminum tri-sec-butoxide (140 mL, 550 mmol). The mixture was heated and became deep amber as distillate was collected until the pot temperature was 162° C. The reaction was heated at 160° C. for 16 h and then cooled to room temperature. The mixture was mixed with tetrahydrofuran (100 mL) and poured onto a 2 L filter frit to isolate the black solid. The solid was stirred on the frit with 6 M HCl (100 mL) and then further washed with water (500 mL). The gray crude product was air-dried overnight. The solid was purified further by vacuum train sublimation (pressure ~5*10^-5 Torr) at a source temperature of 120° C. to afford 12.6 g (48percent) of off-white product. DSC data: peak temp 220° C. (ΔH=126 Jg^-1. IR (KBr, strong abs only): 892, 741, 474 cm^-1. ¹H NMR (500 MHz, d₆-Me₂SO, internal TMS). δ 7.56 (m, 6 lines, 6-H, 8-H), 7.60 (dd, J=2.0, 9.0 Hz, 7-H), 8.09 (m, 1-H, 3-H, 4-H), 8.39 ('d', J=1 Hz, 9-H), 8.57 (s, 5-H), 8.63 (s, 10-H).

Reference： [1] Patent: US2005/12090, 2005, A1,

4
[ 572-83-8 ]
[ 7321-27-9 ]

Reference： [1] Tetrahedron, 2007, vol. 63, # 23, p. 5071 - 5075

5
[ 90-11-9 ]
[ 572-83-8 ]
[ 474688-76-1 ]

Yield	Reaction Conditions	Operation in experiment
64%	With Ki In tetrahydrofuran; n-butyllithium; toluene	3-1) Synthesis of 2-bromo-9,10-di(naphthyl)anthracene 360 g (1.74 mol) of bromonaphthalene was dissolved with THF in a 5 L flask and the temperature was lowered to -78° C. and 1600 ml (1.6 mol) of 1.6M n-BuLi was slowly added dropwise thereto. The mixture was stirred for one hour, and then 200 g (0.68 mol) of 2-bromoanthraquinone was added thereto in a solid state and then the temperature was slowly raised to room temperature and the resultant mixture was stirred. After 12 hours, 500 ml of 2N HCl(aq) was added thereto. Then, an organic layer was isolated and dried over MgSO₄ and condensed under reduced pressure, thereby producing Compound C. The Compound C was used in the subsequent reaction without purification. Compound C, 346 g (2.09 mol) of KI, and 443 g (4.1 mol) of NaH₂PO₂.H₂O were diluted with an acetic acid and then the mixture was refluxed while heating. The temperature was lowered to room temperature and thus a solid was precipitated. The solid was filtered, washed with excess water and MeOH, and re-crystallized with 300 ml of toluene, thereby producing 2-bromo-9,10-di(2-naphthyl)anthracene (230 g, 64percent).

Reference： [1] Patent: US2011/31484, 2011, A1,

6
[ 109-72-8 ]
[ 580-13-2 ]
[ 124-38-9 ]
[ 572-83-8 ]
[ 474688-76-1 ]

Reference： [1] Patent: US2008/299294, 2008, A1,

7
[ 572-83-8 ]
[ 474688-76-1 ]

Reference： [1] Patent: KR101528769, 2015, B1,

[ 572-83-8 ] Synthesis Path-Downstream 1~88

1
[ 572-83-8 ]
[ 605-32-3 ]
[ 72-48-0 ]

Reference： [1]Justus Liebigs Annalen der Chemie,1871,vol. 160,p. 126

2
[ 2159-40-2 ]
[ 572-83-8 ]

Yield	Reaction Conditions	Operation in experiment
74%	With sulfuric acid at 100℃; for 24h; Inert atmosphere;	2-Bromoanthraquinone (BAQ) Into concentrated H2SO4 (800 mL) in 1 L three-necked flask, BBBA (92.85 g, 304.3mmol) was addedat 0 °C. Formed red suspension was stirred at 100 °C under argon atmosphere for 24 h, in which themixture became brown and the disappearance of BBBA (Rf = 0.37) and the appearance of new spot (Rf =0.83) were confirmed by TLC (SiO2, Hexane: AcOEt = 1: 1). After cooling, the mixture was poured intoice water over 20 min, produced white precipitation was obtained by filtration. Into this precipitation,CHCl3 and water were added, and insoluble solid in both organic and aqueous layer was removed byfiltration. The organic layer was washed with water and brine, dried over anhydrous sodium sulfate, andevaporated under reduced pressure. The crude product was recrystallized from CHCl3 to afford BAQ aspale yellow sold (64.85 g, 225.9 mol, 74% yield).The product was identified according to the previouslyreported melting point and 1H NMR spectrum.
	With sulfuric acid at 160℃;
	With sulfuric acid at 120℃;

Reference： [1]Kondo, Shin-ichi; Osawa, Kohei; Tagaya, Hideyuki [Chemistry Letters, 2020, vol. 49, # 3, p. 290 - 294]
[2]Ullmann; Sone [Justus Liebigs Annalen der Chemie, 1911, vol. 380, p. 341]
[3]Heller [Chemische Berichte, 1912, vol. 45, p. 678]

3
[ 572-83-8 ]
[ 77-78-1 ]
[ 103438-63-7 ]

Yield	Reaction Conditions	Operation in experiment
68%	Stage #1: 2-bromoanthracene-9,10-dione With sodium dithionite; tetrabutylammomium bromide In tetrahydrofuran; water at 20℃; for 20h; Inert atmosphere; Stage #2: dimethyl sulfate With potassium hydroxide In tetrahydrofuran; water at 20℃; Inert atmosphere;
	With sodium hydroxide; sodium dithionite; water 1.) C₂H₅OH, H₂O, reflux, 45 min, 2.) 25 deg C, 2 h; Yield given. Multistep reaction;

Reference： [1]Jacobsen, Mikkel F.; Ferapontova, Elena E.; Gothelf, Kurt V. [Organic and Biomolecular Chemistry, 2009, vol. 7, # 5, p. 905 - 908]
[2]Keana, John F. W.; Prabhu, Vaikunth S.; Ohmiya, Shigeru; Klopfenstein, Charles E. [Journal of Organic Chemistry, 1986, vol. 51, # 18, p. 3456 - 3462]

4
[ 572-83-8 ]
[ 7321-27-9 ]

Yield	Reaction Conditions	Operation in experiment
82.02%		In a preferred embodiment,To a 500 mL three-necked flask was added 275.0 g diglyme,68.0 g (0.51 mol) of aluminum chloride solid was added slowly,The control temperature was 60 C,About 20min feeding is completed,The system becomes gray or milky white turbidity.Cooling to 30 ,stand-by.A further 1 L three-necked flask was charged with 49.2 g (0.17 mol) of 2-bromoanthraquinone,200.0 g diglyme,Stir,27.5 g (0.51 mol) of potassium borohydride was added,The system becomes yellow-green turbidity,Heating up to 105 C,And heat for 30 minutes,During the heating process, the system changed from yellow-green turbidity to pink turbidity,Finally into brown turbidity.Insulation is completed,The above-mentioned aluminum chloride solution was slowly added to the system,Control the internal temperature between 90 ~ 110 ,Drop before the first 1/3 of the exothermic reaction,After 2/3 of the process, the endothermic reaction,Dripping with the full range of bubbles,System from brown turbidity into bright yellow turbidity,Finally turned into yellow turbidity.The feeding process is about 20 minutes.Feeding is completed,Quickly cool the water bath to 40 C.The system was poured into concentrated hydrochloric acid / water / ethanol (100 g / 400 g / 300 g)System exotherm, accompanied by a large amount of gas generated.Hydrolysis process control system temperature below 60 .Hydrolysis is completed, cooling to 25 ,Filter,100.0g of water and 100.0g of anhydrous ethanol were leaching filter cake was yellow filter cake,This product is crude product.According to crude:Anhydrous ethanol = 1: 10 by the addition of absolute ethanol,Heating up to 50 ~ 60 ,Stirring for 1.0 hr,Cooling to 25 ~ 30 ,Insulation 0.5hr, suction filter,A small amount of anhydrous ethanol leaching filter cake was white solid,This is the product quality,Dried (50 C, 200 Pa, 5 hr) to give 35.8 g of a white powdery solid,This is the product quality, the yield of 82.02%
61%	With hydrogen iodide; hypophosphorous acid; acetic acid; at 150℃; for 96h;	Compound 1 (2 g, 6.9 mmol), hydroiodic acid (10.6 mL), and hypophosphorous acid (6.4 mL) were dissolved in acetic acid (17 mL). The mixture was stirred for 96 h at 150 C. The reaction mixture was cooled to room temperature. The precipitate was filtered and washed with ethanol. The solid was purified via soxhlet extraction with toluene, yielding compound 2 as a pure yellow solid. Yield: 1.1 g (61%). 1H-NMR (300 MHz, CDCl3, ppm): delta 8.44-8.41 (t, 1H, J = 6.9 Hz), 8.34-8.30 (d, 2H, J = 10.2 Hz), 8.19-7.99 (q, 2H, J = 3.3 Hz), 7.91-7.87 (d, 1H, J = 6.0 Hz), 7.91-7.73 (dd, 1H, J = 9.0, 9.3 Hz), 7.68-7.49 (m, 2H); 13C-NMR (75 MHz, CDCl3, ppm): delta 133.65, 129.89, 129.83, 129.65, 128.87, 128.23, 128.19, 128.12, 126.58, 126.55, 126.05, 126.00, 125.78, 125.37; EI, MS m/z (%): 256 (100, M+).
48%	With aluminum tri-sec-butoxide; In cyclohexanol; at 160 - 162℃; for 16h;	A 1-L, 3-necked flask was fitted with a distillation head and purged with N2. The system was charged with 2-bromoanthraquinone (29.0 g, 101 mmol), cyclohexanol (350 mL), and aluminum tri-sec-butoxide (140 mL, 550 mmol). The mixture was heated and became deep amber as distillate was collected until the pot temperature was 162 C. The reaction was heated at 160 C for 16 h and then cooled to room temperature. The mixture was mixed with tetrahydrofuran (100 mL) and poured onto a 2 L filter frit to isolate the black solid. The solid was stirred on the frit with 6 M HCl (100mL) and then further washed with water (500 mL). The gray crude product was air-dried overnight. The solid was purified further by gradient sublimation at a source temperature of 120C to afford 12.6 g (48%) of off-white product. DSC data: peak temp 220 C (DeltaH = 126 Jg^-1. IR (KBr, strong abs only): 892,741, 474 cm-1. H NMR (500 MHz, d6-Me2SO, internal TMS). delta 7.56 (m, 6 lines, 6-H, 8-H), 7.60 (dd, J = 2.0, 9.0 Hz, 7-H), 8.09 (M, 1-H, 3-H, 4-H), 8.39 ('d', J = 1 Hz, 9-H), 8.57 (s, 5-H), 8.63 (s, 10-H).

26%	With sodium tetrahydroborate; In tetrahydrofuran; isopropyl alcohol; at 0 - 20℃; for 15h;	2-Bromoanthraquinone 10 (8.50 g, 0.0296 mol, 1 equiv) and a 50:50 mixture of isopropyl alcohol and tetrahydrofuran (200 mL) were stirred for 10 minutes at 0 C. forming a yellow suspension. NaBH4 (6.70 g, 0.177 mol, 6.0 equiv.) was added to the suspension at 0 C. The mixture was stirred at 0 C. for three hours, turning red in color. The solution was then warmed to room temperature. Additional NaBH4 (3.35 g, 0.089 mol, 3.0 equiv.) was added to the solution at room temperature and the solution was stirred at room temperature for 12 hours, turning into an orange suspension. Deionized water (10 mL) was added to the solution at room temperature and the solution was stirred at room temperature for an additional 12 hours. The consumption of 2-bromoanthraquinone 10 was monitored by thin-layer chromatography (35% CHCl3/hexane, Rf=0.33). Once the consumption of 2-bromoanthraquinone 10 stopped entirely (it was never fully consumed), the volatiles were removed by rotary evaporation. 3 M HCl was slowly added to the solution until bubbling ceased, then additional 3 M HCl (30 mL) was added. The solution was heated at reflux for 6 hours, turning into an opaque, yellow suspension in the process. The mixture was cooled to room temperature, turning into a transparent solution containing yellow-brown crystals. The contents underwent rotary evaporation as much water as possible. The contents were then vacuum-filtered and washed using deionized water to remove any water, acid and ionic salt, leaving behind a yellow-brown colored solid. The vacuum-filtration receiving flask was changed and the solid was washed with CH2Cl2 through the filter paper. The CH2Cl2 was removed through rotary evaporation. The remaining solid was purified through column chromatography (100% hexane, Rf=0.27), providing 2-bromoanthracene 11 as a white, powdery solid (2.00 g, 26%). 1H NMR (CDCl3): delta 8.42 (s, 1H), 8.34 (s, 1H), 8.18 (d, 1H), 8.01 (m, 2H), 7.87 (d, 1H), 7.50 (m, 3H).
	With sodium tetrahydroborate; In isopropyl alcohol;Inert atmosphere; Reflux;	A mixture of BAQ (32.312 g, 112.5 mmol, 1.0 eq), i-PrOH (400 mL), and NaBH4 (29.543 g, 780.9mmol, 6.9 eq) in three-necked flask was refluxed under argon atmosphere. The mixture gradually becamebrown, and the reaction was monitored by TLC (SiO2, Hex: AcOEt = 8: 2) to confirm the disappearanceof BAQ (Rf = 0.60) and the appearance of a new spot (Rf = 0.73). After 3 h, further NaBH4 (13.131 g,347.1 mmol, total 10 eq) was added because BAQ was still observed by the TLC, then refluxed foranother 17 h. The mixture was cooled to rt, and water (150 mL) was added over 15 min with cooling bywater bath. After the mixture was stirred at 60 C, for 3h, the mixture was cooled to rt, then 3 M HCl (300mL) was added over 15 min with cooling by water bath. This mixture intensely evolved bubble byrefluxing, and became yellowish 11 h later. After addition of CH2Cl2 at rt, the organic layer was washedwith water and saturated NaClaq, then dried on Na2SO4. Concentrated yellowish crude product waspurified by recrystallization from Toluene or AcOEt, or by column chromatography (SiO2, Hexane:CHCl3 = 1: 1) to afford BA as a pale yellow solid (10.5286 g, 36% yield) contaminated with 4-15 mol%anthracene.The product was identified according to the previously reported melting point and 1H NMRspectra.

Reference： [1]Patent: CN106916049,2017,A .Location in patent: Paragraph 0031; 0032; 0033; 0034; 0035; 0036; 0037-0042
[2]Dyes and Pigments,2015,vol. 120,p. 30 - 36
[3]Bulletin of the Korean Chemical Society,2012,vol. 33,p. 3810 - 3816
[4]Organic Letters,2019,vol. 21,p. 5373 - 5377
[5]Journal of Nanoscience and Nanotechnology,2012,vol. 12,p. 4269 - 4273
[6]Tetrahedron Letters,2003,vol. 44,p. 1215 - 1219
[7]Patent: WO2005/19198,2005,A1 .Location in patent: Page/Page column 26-27
[8]Patent: US8410311,2013,B1 .Location in patent: Page/Page column 9
[9]Chemistry Letters,2020,vol. 49,p. 290 - 294

5
[ 117-79-3 ]
[ 572-83-8 ]
[ 84-65-1 ]

Yield	Reaction Conditions	Operation in experiment
37%	With tert.-butylnitrite; copper(ll) bromide; In tetrahydrofuran; acetonitrile; at 0 - 20℃; for 2h;Inert atmosphere;	Copper (II) bromide (35.0 g, 0.157 mol, 3.76 equiv.) was dissolved in freshly-distilled acetonitrile (200 mL) at room temperature to form an opaque dark-green solution. tert-Butyl nitrite (15 mL, 12.9 g, 0.125 mol, 1.49 equiv.) was added at 0 C. and stirred for 30 minutes at 0 C. <strong>[117-79-3]2-Aminoanthraquinone</strong> 9 (18.60 g, 0.0834 mol, 1 equiv.) was dissolved in tetrahydrofuran (THF, 300 mL) at room temperature to form an opaque red-brown solution. The <strong>[117-79-3]2-aminoanthraquinone</strong> 9 solution was quickly added to the copper (II) bromide solution at 0 C. and the solution was stirred for 2 hours at 0 C. with venting of the nitrogen gas by-product every 5 minutes until the bubbling ceased. The consumption of <strong>[117-79-3]2-aminoanthraquinone</strong> 9 was monitored by thin-layer chromatography (100% CHCl3, Rf=0.32). Once the <strong>[117-79-3]2-aminoanthraquinone</strong> 9 was consumed, the THF and acetonitrile solvents were removed from the mixture via rotary evaporation to give a brown and black solid residue. The solid was rinsed with deionized water to form a suspension. The resulting slurry was vacuum filtered and rinsed with deionized water. The filtration receiving flask was changed and the solid was washed with CH2Cl2 through the filter paper, leaving a red-brown solid by-product and forming a yellow-brown solution. The CH2Cl2 was removed from the solution via rotary evaporation, leaving a yellow solid consisting of the product 2-bromoanthraquinone 10 and by-product anthraquinone. The desired product was separated and purified from the unwanted by-product through column chromatography (35% CHCl3/hexane, Rf=0.33 and Rf=0.28 respectively), providing 2-bromoanthraquinone 10 as a light yellow solid (11.2 g; 37%). 1H NMR (CDCl3): delta 8.42 (d, 1H), 8.30 (m, 2H), 8.16 (d, 1H), 7.91 (dd, 1H), 7.80 (m, 2H).

Reference： [1]Tetrahedron Letters,2003,vol. 44,p. 1215 - 1219
[2]Patent: US8410311,2013,B1 .Location in patent: Page/Page column 8; 9

6
[ 117-79-3 ]
[ 572-83-8 ]

Yield	Reaction Conditions	Operation in experiment
89%	With tert.-butylnitrite; copper(ll) bromide; In acetonitrile; at 65℃; for 3h;	EXAMPLES Synthesis Example 1: Synthesis of Compound 1 1-1) Synthesis of 2-bromoanthraquinone 200 g (0.896 mol) of <strong>[117-79-3]2-aminoanthraquinone</strong>, 240.13 g (1.075 mol) of CuBr2, 4L of acetonitrile, and 138.58 g (1.344 mol) of t-butylnitrite were loaded into a 10 L reactor and then the temperature was increased to 65C. After 3-hour reaction, the temperature was decreased to room temperature and then 3 L of 2N HCl was added thereto, thereby producing a solid. The solid was filtered and washed with 10 L of water, thereby producing a dark brown solid (203 g, 89%).
75%		18 g (81 mmol) of copper bromide and 12 mL (101 mmol) of t-butyl nitrite were dispersed into acetonitrile at 65C, and then 15 g (67 mmol) of <strong>[117-79-3]2-aminoanthraquinone</strong> were dropped while the solution was vigorously stirred. The mixture was stirred until the generation of a gas was completely stopped. Then, the temperature of the mixture was cooled to room temperature, and 1 L of 20-mass% hydrochloric acid was added. After that, the resultant was extracted with dichloromethane. An organic layer was dried with magnesium sulfate, and the solvent was distilled off under reduced pressure. The residue was purified by means of silica gel column chromatography to obtain 14 g of 2-bromoanthraquinone (75% yield).
75%	With hydrogen bromide; copper(I) bromide; In water; at 65℃;	Synthesis of Intermediate 1a; 10 g of copper bromide (44 mmol) and 8 g of <strong>[117-79-3]2-aminoanthraquinone</strong> (35.8 mmol) were added to 250 ml of bromic acid, and the mixture was heated at 65 C. After gas generation was terminated, the mixture was cooled to room temperature. Then, the mixture was added to 1,000 ml of 20% aqueous hydrochloric acid, and was extracted with dichloromethane. Moisture remaining in an organic layer was removed with anhydrous MgSO4, and the resulting product was dried under pressure. The resulting product was purified by column chromatography (dichloromethane:normal hexane=4:1) to obtain 7.7 g of Intermediate 1a (yield 75%).

75%	With bromic acid; copper(ll) bromide; In water; at 65℃;	Synthesis Example 1 : Synthesis of Compound 1; Compound 1 was synthesized through Reaction Scheme 1 below:; Synthesis of Intermediate 1a; 10 g of copper bromide (44 mmol) and 8 g of <strong>[117-79-3]2-aminoanthraquinone</strong> (35.8 mmol) were added to 250 ml of bromic acid, and the mixture was heated at 65C. After gas generation was terminated, the mixture was cooled to room temperature. Then, the mixture was added to 1,000 ml of 20% aqueous hydrochloric acid, and was extracted with dichloromethane. Moisture remaining in an organic layer was removed with anhydrous MgSO4, and the resulting product was dried under pressure. The resulting product was purified by column chromatography (dichloromethane:normal hexane=4:1) to obtain 7.7 g of Intermediate 1a (yield 75%).
75%	With tert.-butylnitrite; copper(I) bromide; In acetonitrile; at 65℃; for 0.0833333h;	Synthesis of Compound 104Copper bromide (CuBr2, 17.9 g, 80.0 mmol) and t-butyl nitrite (12 mL, 101 mmol) were dispersed in acetonitrile (250 mL) at 65 C., and the dispersion mixture was agitated. To the mixture, <strong>[117-79-3]2-aminoanthraquinone</strong> (15.0 g, 67.2 mmol) was slowly added dropwise over about 5 minutes, which evolved nitrogen gas. After gas evolution was completed, the mixture was cooled to room temperature, quenched with 20% hydrochloric acid (1,000 mL), and extracted with dichloromethane. The organic extract was dried with magnesium sulfate, and concentrated under reduced pressure. Purification by column chromatography (dichloromethane/n-hexane=4/1) yielded Compound 104 (14.5 g, 75%). The analysis result of the compound: m.p. 207.5 C.; 1H NMR (500 MHz, CDCl3), 8.43 (d, J=1.8 Hz, 1H), 8.30 (m, 2H), 8.17 (d, J=8.3 Hz, 1H), 7.91 (dd, J=1.8, 8.3 Hz, 1H), 7.82 (m, 2H); MS (M+) 286; Anal. Calc'd. for C14H7BrO2: C, 58.57; H, 2.46; Br, 27.83; O, 11.14. Found: C, 58.88; H, 2.39; Br, 27.80; O, 10.93.
75%	With tert.-butylnitrite; copper(ll) bromide; In acetonitrile; at 65℃;	Copper bromide (CuBr2, 17.9 g, 80.0 mmol) and t-butyl nitrite (12 mL, 101 mmol) were dispersed in acetonitrile (250 mL) at 65C, and the dispersion mixture was agitated. To the mixture, <strong>[117-79-3]2-aminoanthraquinone</strong> (15.0 g, 67.2 mmol) was slowly added dropwise over about 5 minutes, which evolved nitrogen gas. After gas evolution was completed, the mixture was cooled to room temperature, quenched with 20% hydrochloric acid (1,000 mL), and extracted with dichloromethane. The organic extract was dried with magnesium sulfate, and concentrated under reduced pressure. Purification by column chromatography (dichloromethane/n-hexane = 4/1) yielded Compound 104 (14.5 g, 75%). The analysis result of the compound: m. p. 207. 5 C ; 1H NMR (500 MHz, CDCl3), 8.43 (d, J = 1.8 Hz, 1H), 8.30 (m, 2H), 8.17 (d, J = 8.3 Hz, 1H), 7.91 (dd, J = 1.8, 8.3 Hz, 1H), 7.82 (m, 2H); MS (M+) 286; Anal. Calc'd. for CiBrO, : C, 58.57 ; H, 2.46 ; Br, 27.83 ; O, 11.14. Found: C, 58. 88; H, 2.39 ; Br, 27.80 ; O, 10.93.
75%	With tert.-butylnitrite; copper(ll) bromide; In acetonitrile; at 65℃; for 0.0833333h;	1-A. Production of compound Ia; [59] After copper bromide (18 g, 80.0 mmol) and t-butyl nitride (12 mL, 101 mmol) were dispersed in acetonitrile (250 mL) at 650C and then agitated, <strong>[117-79-3]2-aminoanthraquinone</strong> (15 g, 67.2 mmol) was slowly added thereto drop by drop for 5 min. After completion of generation of gas, the reaction solution was cooled to normal temperature and then added to 20% hydrochloric acid aqueous solution (1 L), and extraction was performed <n="15"/>with dichloromethane. After the water residue was removed from the organic layer by using anhydrous magnesium sulfate, the resulting organic layer was dried at reduced pressure. Separation was performed by using column chromatography to obtain a light yellow compound Ia (14.5 g, 75%).[60] MS [M] = 287
75%	With tert.-butylnitrite; copper(ll) bromide; In acetonitrile; at 65℃; for 0.0833333h;	(Preparation of starting material represented by Chemical Formula d) [0045] Copper bromide (CuBr2, 17.9 g, 80.0 mmol) and t-butyl nitrite (12 mL, 101 mmol) were dispersed in acetonitrile (250 mL) at 65C, and agitated, and then <strong>[117-79-3]2-aminoanthraquinone</strong> (15.0 g, 67.2 mmol) was slowly added dropwise over 5 minutes. After gas evolution was completed, the mixture was cooled to room temperature, quenched with 20 % hydrochloric acid (1,000 mL), and extracted with dichloromethane. The organic extract was dried over magnesium sulfate and concentrated under reduced pressure. Purification by column chromatography (dichloromethane/n-hexane = 4/1) yielded a compound of the Chemical Formula d (14.5 g, 75%). [0046] The analysis result of the compound is as follows: m.p. 207.5 C; 1 H NMR (500 MHz, CDCl3), 8.43 (d, J = 1.8 Hz, 1 H), 8.30 (m, 2H), 8.17 (d, J = 8.3 Hz, 1 H), 7.91 (dd, J = 1.8, 8.3 Hz, 1 H), 7.82 (m, 2H); MS (M+) 286; Anal. Calc'd. for C14H7BrO2: C, 58.57; H, 2.46; Br, 27.83; O, 11.14. Found: C, 58.88; H, 2.39; Br, 27.80; O, 10.93.
75%	With tert.-butylnitrite; copper(ll) bromide; In acetonitrile; at 65℃;	(1) Synthesis of compound <la> (2-bromoanthraquinone)Copper bromide (CuBr2) of 18g (81 mmol) and tert-butyl nitrite of 12ml <n="48"/>(101 mmol) were dispersed by acetonitrile having a temperature of 65 "C , and <strong>[117-79-3]2-aminoanthraquinone</strong> of 15g (67 mmol) was added while the mixture was vigorouslystirred. The mixture was stirred until nitrogen gas was not generated at all and thencooled to room temperatures. After 20% hydrochloric acid of IL was added, themixture was extracted by dichloromethane. An organic layer was dried by sulfurtrioxide magnesium, and a solvent was removed from the mixture under reducedpressure. The mixture was purified by silica gel column chromatography to obtain afollowing compound <la> of 14g (75%).Compound <la>
62%	With tert.-butylnitrite; In acetonitrile; at 65℃; for 2h;	<strong>[117-79-3]2-Aminoanthraquinone</strong> (3 g, 13.44 mmol), tert-butyl nitrite (3.69 mL, 30.9 mmol), and copper (I) bromide (6.9 g, 30.9 mmol) were added to acetonitrile (50 mL). The mixture was stirred for 2 h at 65 C. The reaction mixture was cooled to room temperature. The reaction was quenched with 6 N HCl. The precipitate was filtered, washed with chloroform, and dried in a vacuum desiccator to give compound 1 as a pure brown solid. Yield: 2.4 g (62%). 1H-NMR (300 MHz, CDCl3, ppm): delta 8.42 (d, 1H, J = 2.1 Hz), 8.32-8.28 (m, 2H), 8.18-8.15 (d, 1H, J = 8.1 Hz), 7.94-7.90 (dd, 1H, J = 2.1, 1.8 Hz), 7.84-7.81 (q, 2H, J = 3.3 Hz); 13C-NMR (75 MHz, CDCl3, ppm): delta 182.36, 137.16, 134.48, 134.36, 133.13, 130.02, 129.02, 127.38, 127.34; EI, MS m/z (%): 286 (100, M+).
58%		(i) Synthesis of 2-bromo-9,10-anthraquinone.; A synthetic scheme of 2-bromo-9,10-anthraquinone is shown in (C-I). [0274][0275] 46 g (206 mmol) of copper bromide (II) and 500 mL of acetonitrile were put into a 1 L three-neck flask, and was added 17.3 g (168 mmol) of tert-butyl nitrite into the <n="133"/>suspension, which was followed by heating at 65 0C. Thereafter, 25 g (111.0 mmol) of<strong>[117-79-3]2-amino-9,10-anthraquinone</strong> was added into the mixture, and then the mixture was stirred for 6 hours at the same temperature. After the reaction, the reaction mixture was poured into 3M-hydrochloric acid and stirred for 3 hours. Then the precipitate was filtered and washed with water and then with ethanol. The precipitate was dissolved in toluene, and the resulting solution was filtered through Florisil, celite, and then alumina.The filtrate was concentrated, and the residue was recrystallized with chloroform and hexane, giving 18.6 g of 2-bromo-9,10-anthraquinone as a cream-colored solid in 58% yield.
58%	With tert.-butylnitrite; copper(ll) bromide; In acetonitrile; at 65℃; for 6h;	EXAMPLE 1; In this example, a synthetic method of 9,10-bis(4-fluorophenyl)-2-[N-phenyl-N-(9-phenyl-9H-carbazol-3-yl)amino]anthracene (abbreviation: 2PCAFPA), which is the anthracene derivative of the present invention represented by Structural Formula (201), will be specifically described. [Step 1] Synthesis of 2-bromo-9,10-bis(4-fluorophenyl)anthracene; (i) Synthesis of 2-bromo-9,10-anthraquinone; A synthetic scheme of 2-bromo-9,10-anthraquinone is shown in (C-1). 46 g (206 mmol) of copper bromide(II) and 500 mL of acetonitrile were put into a 1 L three-neck flask, and 17.3 g (168 mmol) of tert-butyl nitrite was added into the suspension, which was followed by heating at 65 C. Thereafter, 25 g (111.0 mmol) of <strong>[117-79-3]2-amino-9,10-anthraquinone</strong> was added into the mixture, and then the mixture was stirred for 6 hours at the same temperature. After the reaction, the reaction mixture was poured into a 3M hydrochloric acid and stirred for 3 hours. Then the precipitate was filtered and washed with water and then with ethanol. The precipitate was dissolved in toluene, and the resulting solution was filtered through Florisil, celite, and then alumina. The filtrate was concentrated, and the residue was recrystallized with chloroform and hexane, giving 18.6 g of 2-bromo-9,10-anthraquinone as a cream-colored solid in 58% yield.
58%	With tert.-butylnitrite; copper(ll) bromide; In acetonitrile; at 65℃; for 6h;	Step 1: Synthesis of 2-bromo-9,10-anthraquinone First, 46 g (206 mmol) of Copper(II) bromide and 500 mL of acetonitryl were put into a 1 L three-neck flask, and 17.3 g (168 mmol) of tert-butyl nitrite was added thereto. While this mixture was heated at 65 C., 25 g (111 mmol) of <strong>[117-79-3]2-amino-9,10-anthraquinone</strong> was added to the mixture. This mixture was stirred for six hours at the same temperature. After the stirring, this reaction solution was poured into about 500 mL (3.0 mol/L) of hydrochloric acid and this mixture was stirred for 3 hours. After the stirring, the mixture including precipitate was filtered and the residue was washed with water and ethanol. After the washing, the residue was dissolved in toluene and this solution was subjected to suction filtration through Florisil (produced by Wako Pure Chemical Industries, Ltd., Catalog No. 540-00135), Celite (produced by Wako Pure Chemical Industries, Ltd., Catalog No. 531-16855), and alumina. The obtained filtrate was concentrated, so that a solid substance was obtained. The obtained solid substance was recrystallized with chloroform/hexane, so that 18.6 g of a light-yellow powdered solid substance, 2-bromo-9,10-anthraquinone, which was the object of the synthesis, was obtained in 58% yield. The synthesis scheme of Step 1 is shown by (a-1) below.
58%	With tert.-butylnitrite; copper(ll) bromide; In acetonitrile; at 65℃; for 6h;	(i) Synthesis of 2-Bromo-9,10-anthraquinoneA synthesis scheme of 2-bromo-9,10-anthraquinone is illustrated in (C-I). [0345] <n="131"/> [0346]In a IL three-neck flask were put 46 g (206 mmol) of copper(II) bromide and 500 mL of acetonitrile. To the mixture was added 17.3 g (168 mmol) of tert-butyl nitrite. This mixture was heated to 65 C. While the mixture was heated, to this mixture was added 25 g (111 mmol) of <strong>[117-79-3]2-amino-9,10-anthraquinone</strong>. This mixture was stirred at the same temperature for 6 hours. Then, this solution was poured into about 500 mL of hydrochloric acid (3 mol/L). This mixture was stirred for 3 hours. Then, the solid precipitated from the mixture was filtered off. The obtained residue was washed with water and ethanol. Then, the residue was dissolved in toluene, and this solution was suction filtered through Florisil (a product of Wako Pure Chemical Industries, Ltd., Catalog No. 540-00135), Celite (a product of Wako Pure Chemical Industries, Ltd., Catalog No. 531-16855), and alumina. The obtained filtrate was concentrated to give a solid. The solid was recrystallized with chloroform/hexane to give 2-bromo-9,10-anthracene, which was the object of the synthesis, as 18.6 g of a light yellow powdered solid in a yield of 58 %. [0347] (ii) Synthesis of 2-Bromo-9,10-dihydroanthracene-9,10-diol
58%		46 g (0.20 mol) of copper(II) bromide and 500 mL of acetonitrile were put in a 1 L three-neck flask. Further, 17 g (0.17 mol) of tert-butyl nitrite was added thereto, and the mixture was heated to 65 C. 25 g (0.11 mol) of <strong>[117-79-3]2-amino-9,10-anthraquinone</strong> was added to the mixture and stirred for six hours at the same temperature. After reaction, the reaction solution was poured into 500 mL of hydrochloric acid (3 mol/L) and this suspension was stirred for three hours, so that a solid substance was precipitated. The precipitation was collected by suction filtration and washed with water and ethanol while being subjected to suction filtration. The residue was dissolved in toluene and was subjected to suction filtration through Florisil (manufactured by Floridin Company), Celite (manufactured by Celite Co., Ltd.), and alumina, and the filtrate was obtained. The obtained filtrate was concentrated, so that a solid substance was obtained. The obtained solid substance was recrystallized with a mixed solvent of chloroform and hexane, so that 18.6 g of a milky white powdered solid substance, 2-bromo-9,10-anthraquinone was obtained in 58% yield.
		Examples; Synthesis Example 1: Synthesis of Compound 1; Compound 1 was synthesized according to Reaction Scheme 1.; Synthesis of Intermediate 1a; Copper bromide (10g, 44 mmol) and <strong>[117-79-3]2-aminoanthraquinone</strong> (8g, 35.8 mmol) were added to 250 ml of bromic acid, and the reaction mixture was heated to 65 C. When gas generation was stopped, the reaction solution was cooled to room temperature, added to a 20% HCl solution (1,000 ml), and extracted with dichloromethane. The organic layer was dried over anhydrous magnesium sulfate to remove residual moisture, dried under reduced pressure, and purified by column chromatography (dichloromethane/n-hexane = 4:1) to yield intermediate 1a (7.7g).
	With bromic acid; copper(ll) bromide; In water; at 65℃;	Examples Synthesis Example 1: Synthesis of Compound 1; Compound 1 was synthesized through Reaction Scheme 1 below: [Show Image] Synthesis of Intermediate 1a 10 g (44 mmol) of copper bromide and 8 g (35.8 mmol) of <strong>[117-79-3]2-aminoanthraquinone</strong> were added to 250 ml of bromic acid and the mixture was heated at 65C. After gas generation was completed, the mixture was cooled to room temperature and added to 1000 ml of a 20% HCl solution. The resulting product was subjected to extraction using dichloromethane. Residual moisture was removed using anhydrous magnesium sulfate and the resulting product was dried under reduced pressure. The dried resulting product was separated using column chromatography (dichloromethane:n-hexane =4: 1) to obtain 7.7 g of Intermediate 1 a.
	With tert.-butylnitrite; copper(I) bromide; In acetonitrile; at 60℃;	18.3 g of copper bromide and 12 mlTert-butyl nitrite was dispersed in acetonitrile,Heated to 60 C,A solution of 15.3 g of <strong>[117-79-3]2-aminoanthraquinone</strong>,Stirring the reaction,After no gas is produced,Cooling to room temperature,Add hydrochloric acid,Extracted with dichloromethane,After drying, the solvent was distilled off to give 2-bromoanthraquinone.

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7
[ 572-83-8 ]
[ 591-51-5 ]
[ 860530-98-9 ]

Yield	Reaction Conditions	Operation in experiment
	In tetrahydrofuran; dibutyl ether at 20℃; for 12h;	1.1.ii (ii) Synthesis of 2-bromo-9,10-diphenyl-9,10-dihydroanthracene-9,10-diol.; A synthetic "scheme of2-bromo-9,10-diphenyl-9,10-dihydroanthracene-9,10-diol is shown in (C-2). [0277][0278]4.90 g (16.95 mmol) of 2-bromo-9,10-anthraquinone was put into a 300 mL three-neck flask, and the atmosphere of the flask was substituted with nitrogen. Into the flask was added 100 mL of tetrahydrofuran (THF), and 17.76 mL (37.29 mmol) of a dibutyl ether-solution of phenyllithium was dropwised, which was followed by stirring for about 12 hours at room temperature. After the reaction, the solution was washed with water, and the aqueous layer was extracted with ethyl acetate. The organic layer was dried over magnesium sulfate, filtered and concentrated to give 2-bromo-9,10-diphenyl-9,10-dihydroanthracene-9,10-diol as the target compound.
	In tetrahydrofuran at 20℃; Inert atmosphere;	1.2 Step 2: Synthesis of 2-bromo-9,10-diphenylantracene First, 4.90 g (17.0 mmol) of 2-bromo-9,10-anthraquinone obtained in Step 1 was put into a 300 mL three-neck flask, the atmosphere in the flask was substituted by nitrogen, and then 100 mL of tetrahydrofuran (THF) was added thereto. Then, 17.8 mL (37.3 mmol) of phenyllithium was dropped into this solution. After the drop, this solution was stirred at room temperature for 15 hours. After the stirring, the solution was washed with water and an aqueous layer was extracted with ethyl acetate. The extracted solution and an organic layer were dried with magnesium sulfate. After the mixture was dried, the mixture was subjected to gravity filtration, and the filtrate was concentrated, so that 2-bromo-9,10-diphenylanthracene-9,10-diol was obtained.
	In tetrahydrofuran at 20℃; Inert atmosphere;	1.1.ii; C.2 A synthesis scheme of 2-bromo-9,10-dihydroanthracene-9,10-diol is illustrated in (C-2). [0348] [0349] In a 300 mL three-neck flask was put 4.90 g (17.0 mmol) of 2-bromo-9,10-anthraquinone, and the atmosphere in the flask was replaced with nitrogen. To the flask was added 100 mL of tetrahydrofuran (THF), and 17.8 mL (37.3 mmol) of phenyllithium was dropped into this solution. After the completion of the dropping, this solution was stirred at room temperature for 15 hours. Then, this solution was washed with water, and the aqueous layer was extracted with ethyl acetate. The extract solution and the organic layer were combined and dried with magnesium sulfate. Then, this mixture was gravity filtered. The obtained filtrate was concentrated to give 2-bromo-9,10-dihydroanthracene-9,10-diol, which was the object of the synthesis. [0350] (iii) Synthesis of 2-Bromo-9,10-diphenylanthracene.

Stage #1: 2-bromoanthracene-9,10-dione; phenyllithium In tetrahydrofuran at 20℃; for 12h; Inert atmosphere; Stage #2: With water In tetrahydrofuran

1.1.ii 4.9 g (17 mmol) of 2-bromo-9,10-anthraquinone was put in a 300 mL three-neck flask, the atmosphere in the flask was substituted by nitrogen, and 100 mL of tetrahydrofuran (THF) was added thereto and dissolved well. Then, 18 mL (37 mmol) of phenyllithium was dropped into this solution and stirred at room temperature for about 12 hours. After reaction, the solution was washed with water, and an aqueous layer was extracted with ethyl acetate. The extracted solution and an organic layer were dried with magnesium sulfate. After drying, the mixture was subjected to suction filtration, and the filtrate was concentrated, so that 2-bromo-9,10-diphenyl-9,10-dihydroanthracene-9,10-diol (about 7.6 g) was obtained.

Reference： [1]Current Patent Assignee: SEMICONDUCTOR ENERGY LABORATORY CO.,LTD. - WO2007/125934, 2007, A1 Location in patent: Page/Page column 131
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8
[ 2052-07-5 ]
[ 572-83-8 ]
[ 55365-18-9 ]

Yield	Reaction Conditions	Operation in experiment
	Stage #1: n-butyllithium; 2-Bromobiphenyl In tetrahydrofuran; hexane at -78℃; for 5h; Stage #2: 2-bromoanthracene-9,10-dione In tetrahydrofuran at -78 - 20℃; for 12h;	3.1 [Embodiment 3]; [0311]In this embodiment, a synthetic method of9,10-di(2-biphenylyl)-2-[N-(4-diphenylaminophenyl)-N-phenylamino]anthracene (abbreviation: 2DPABPhA), which is the anthracene derivative of the present invention represented by Structural Formula (115), is specifically described. ; [0312][0313][Step 1] Synthesis of 9,10-di(2-biphenylyl)-2-bromoanthracene.A synthetic scheme of 9,10-di(2-biphenylyl)-2-bromoanthracene is shown in (C-8) to (C-IO). [0314][0315] [0317] 22.84 g (98.00 mmol) of 2-bromobiphenyl was put into a 500 mL three-neck flask, and the atmosphere of the flask was substituted with nitrogen. Into the flask was added 100 mL of tetrahydrofuran (THF), followed by dropwising 68.66 mL (107.80 mmol) of rø-butyllithium (1.57 mol/L hexane solution) at -78 0C. After stirring for 5 hours, 160 mL of THF containing 8.5 g (29.40 mmol) of 2-bromo-9,10-anthraquinone was dropwised to this solution under nitrogen, and the solution was stirred for about 12 hours while the reaction temperature was allowed to gradually increase to room temperature. After the reaction, into the solution was added water, and the precipitate formed was filtered, giving9,10-di(2-biphenylyl)-2-bromo-9,10-dihydroanthracene-9,10-diol as a cream colored solid.

Reference： [1]Current Patent Assignee: SEMICONDUCTOR ENERGY LABORATORY CO.,LTD. - WO2007/125934, 2007, A1 Location in patent: Page/Page column 141-142

9
[ 572-83-8 ]
[ 55365-18-9 ]
[ 474688-70-5 ]

Yield	Reaction Conditions	Operation in experiment
	In tetrahydrofuran; hexane at -78 - 20℃; for 12h;	3.1 [Embodiment 3]; [0311]In this embodiment, a synthetic method of9,10-di(2-biphenylyl)-2-[N-(4-diphenylaminophenyl)-N-phenylamino]anthracene (abbreviation: 2DPABPhA), which is the anthracene derivative of the present invention represented by Structural Formula (115), is specifically described. ; [0312][0313][Step 1] Synthesis of 9,10-di(2-biphenylyl)-2-bromoanthracene.A synthetic scheme of 9,10-di(2-biphenylyl)-2-bromoanthracene is shown in (C-8) to (C-IO). [0314][0315] [0317] 22.84 g (98.00 mmol) of 2-bromobiphenyl was put into a 500 mL three-neck flask, and the atmosphere of the flask was substituted with nitrogen. Into the flask was added 100 mL of tetrahydrofuran (THF), followed by dropwising 68.66 mL (107.80 mmol) of rø-butyllithium (1.57 mol/L hexane solution) at -78 0C. After stirring for 5 hours, 160 mL of THF containing 8.5 g (29.40 mmol) of 2-bromo-9,10-anthraquinone was dropwised to this solution under nitrogen, and the solution was stirred for about 12 hours while the reaction temperature was allowed to gradually increase to room temperature. After the reaction, into the solution was added water, and the precipitate formed was filtered, giving9,10-di(2-biphenylyl)-2-bromo-9,10-dihydroanthracene-9,10-diol as a cream colored solid.

Reference： [1]Current Patent Assignee: SEMICONDUCTOR ENERGY LABORATORY CO.,LTD. - WO2007/125934, 2007, A1 Location in patent: Page/Page column 141-142

10
[ 572-83-8 ]
C₁₄H₁₁Br [ No CAS ]
[ 7321-27-9 ]

Reference： [1]Tetrahedron,2007,vol. 63,p. 5071 - 5075

11
[ 572-83-8 ]
[ 103438-64-8 ]

Yield	Reaction Conditions	Operation in experiment
44%	With methyllithium In tetrahydrofuran at -78℃; for 3h; Inert atmosphere; Darkness;	Preparation of 2-bromo-9,10-dimethylanthracene (35-2) Preparation of 2-bromo-9,10-dimethylanthracene (35-2) In a 4-neck 10 L flask, 2-bromoanthraquinone (compound 35-1, 500 g, 1.74 mole) was dissolved in anhydrous THF (6.5 L). The solution was cooled to -78° C. under nitrogen atmosphere and MeLi (2.39 L, 3.83 mole) was added dropwise over 2 h. The darkened reaction mixture was stirred for another 1 h at -78° C. and then was allowed to reach room temperature overnight. The reaction was quenched with saturated NH4Cl (1.5 L). The organic layer was separated, washed with H2O, dried over anhydrous Na2SO4, and concentrated under reduced pressure. The resulting yellow solid was then dissolved in MTBE (3.4 L). A solution of SnCl2.2H2O (2.12 kg, 9.40 mole) in concentrated HCl (1.67 L) was added under ice bath cooling over 30 min. The reaction mixture was stirred for 3 h at room temperature, then transferred to a separatory funnel, washed with H2O, dried over anhydrous sodium sulfate, and concentrated under reduced pressure. The residue was purified by column chromatography (SiO2, eluent: petroleum ether/DCM 20:1) to give the title compound 35-2 (220 g, 44%) as a yellow solid.
	Multi-step reaction with 2 steps 1: tetrahydrofuran; diethyl ether / 1 h / -78 - 25 °C 2: 56 percent / SnCl₂, conc. aq. HCl / tetrahydrofuran; diethyl ether / 0.33 h
	Multi-step reaction with 2 steps 1: tetrahydrofuran 2: tin(ll) chloride; hydrogenchloride / water; diethyl ether

Multi-step reaction with 2 steps 1: tetrahydrofuran 2: hydrogenchloride; tin(ll) chloride / diethyl ether

Reference： [1]Current Patent Assignee: PROFUSA INC - US2018/179233, 2018, A1 Location in patent: Paragraph 0362; 0363
[2]Keana, John F. W.; Prabhu, Vaikunth S.; Ohmiya, Shigeru; Klopfenstein, Charles E. [Journal of Organic Chemistry, 1986, vol. 51, # 18, p. 3456 - 3462]
[3]Kim, Sooyeon; Tachikawa, Takashi; Fujitsuka, Mamoru; Majima, Tetsuro [Journal of the American Chemical Society, 2014, vol. 136, # 33, p. 11707 - 11715]
[4]Current Patent Assignee: OSAKA UNIVERSITY - US10564164, 2020, B2

12
[ 572-83-8 ]
[ 98-80-6 ]
[ 6485-97-8 ]

Yield	Reaction Conditions	Operation in experiment
93.7%	With tetrakis(triphenylphosphine) palladium⁽⁰⁾; potassium carbonate In ethanol; water; toluene for 8h; Inert atmosphere; Reflux;	4 Synthetic Example 4 Synthesis of Compound A17 Under nitrogen protection, intermediate 2-bromoanthraquinone (1eq), phenylboronic acid were added to a three-vial bottle equipped with a mechanical stirring device.(1 eq), potassium carbonate 5 eq, Pd(Pph3) 4 (2%), toluene 1000 ml + ethanol 500 ml + water 300 ml, stirring was turned on, heating to reflux, reaction for 8 h. The organic phase was subjected to silica gel column chromatography, concentrated, and recrystallized from toluene to give yellow powder M1 (9.0 g, 93.7%).
93.7%	With tetrakis(triphenylphosphine) palladium⁽⁰⁾; potassium carbonate In ethanol; water; toluene for 8h; Inert atmosphere; Reflux;	4 Under nitrogen protection,Add to a three-vial bottle equipped with a mechanical stirrerIntermediate 2-bromoanthraquinone (1 eq),Phenylboronic acid (1eq),Potassium carbonate (5eq),Pd(Pph3)4(2%),Toluene 1000 ml + ethanol 500 ml + water 300 ml, stirring turned on, heating to reflux, reaction 8 h.Organic phase silica gel column chromatography, concentrated,Recrystallization from toluene gave yellow powder M1 (9.0 g, 93.7%).
74%	With potassium carbonate In ethanol; toluene for 3h; Heating / reflux;	2-bromoanthraquinone (24.2 mmol, 6.96 g) was completely dissolved in 120 mL of toluene, thereto phenylboronic acid (29.0 mmol, 3.54 g), 50 mL of 2M potassium carbonate solution, tetrakis(triphenylphosphine)palladium(0) (0.73 mmol, 0.84 g), and 10 mL of ethanol were added. Reflux was then conducted for 3 hours. After the reaction was completed, it was cooled to room temperature, filtered, and washed a few times using water and ethanol. A filtered solid product was separated using column chromatography and crystallized in ethanol to produce 5.10 g of the compound of Formula a (17.9 mmol, 74%).

47%

With tetrakis(triphenylphosphine) palladium⁽⁰⁾; potassium carbonate In water; toluene at 130℃; for 12h;

Reference： [1]Current Patent Assignee: BEIJING ETERNAL MATERIAL TECHNOLOGY CO LTD - CN107915732, 2018, A Location in patent: Paragraph 0096; 0097; 0100
[2]Current Patent Assignee: BEIJING ETERNAL MATERIAL TECHNOLOGY CO LTD - CN107954942, 2018, A Location in patent: Paragraph 0103; 0106
[3]Current Patent Assignee: LG CHEM CO.,LTD. - US2006/46097, 2006, A1 Location in patent: Page/Page column 8
[4]Chiba, Hiroshi; Nishida, Jun-Ichi; Yamashita, Yoshiro [Chemistry Letters, 2012, vol. 41, # 5, p. 482 - 484]

13
[ 572-83-8 ]
[ 474688-75-0 ]

Yield	Reaction Conditions	Operation in experiment
94%	Stage #1: 2-bromonaphthalene With tert.-butyl lithium In tetrahydrofuran; pentane at -78℃; for 1h; Stage #2: 2-bromoanthracene-9,10-dione In tetrahydrofuran; pentane	2.2-a In an argon atmosphere, 11 g (53 mmol) of 2-bromonaphthalene were dissolved into 100 mL of dehydrated tetrahydrofuran (THF), and the temperature of the solution was cooled to -78° C. Then, 45 mL of t-butyllithium (in pentane, 1.5 mol/L) were dropped. After the mixture had been stirred at -78° C for 1 hour, 6.3 g (22 mmol) of 2-bromoanthraquinone were added. After an aqueous solution of ammonium chloride had been added, the resultant was extracted with dichloromethane. An organic layer wasdried with magnesiumsulfate, and the solvent was distilled off under reduced pressure. The resultant solid was washed with ethanol to obtain 11 g of 2-bromo-9,10-di(2-naphtyl)-9,9,10,10-tetrahydroanthracene-9,10 -diol (94% yield).

Reference： [1]Current Patent Assignee: IDEMITSU KOSAN CO LTD - EP1734038, 2006, A1 Location in patent: Page/Page column 44

14
[ 572-83-8 ]
[ 860530-98-9 ]

Yield	Reaction Conditions	Operation in experiment
90%	Stage #1: bromobenzene With tert.-butyl lithium In tetrahydrofuran at -78℃; for 1h; Stage #2: 2-bromoanthracene-9,10-dione In tetrahydrofuran at -78℃; Stage #3: With water; ammonium chloride In tetrahydrofuran
90%	Stage #1: bromobenzene With tert.-butyl lithium In tetrahydrofuran; pentane at -78℃; for 1h; Stage #2: 2-bromoanthracene-9,10-dione In tetrahydrofuran; pentane	1.1-b; 4.4-b In an argon atmosphere, 5.4 mL (52 mmol) of bromobenzene were dissolved into 100 mL of dehydrated tetrahydrofuran (THF), and the temperature of the solution was cooled to -78° C. Then, 45 mL of t-butyllithium (in pentane, 1.5 mol/L) were dropped. After the mixture had been stirred at -78° C for 1 hour, 4.9 g (17 mmol) of 2-bromoanthraquinone were added. After an aqueous solution of ammonium chloride had been added, the resultant was extracted with dichloromethane. An organic layer was dried with magnesium sulfate, and the solvent was distilled off under reduced pressure. The resultant solid was washed with ethanol to obtain 6.8 g of 2-bromo-9,10-diphenyl-9,9,10,10-tetrahydroanthracene-9,10-diol (90% yield).
	With nitrogen; phenyllithium In tetrahydrofuran	1.ii (ii) (ii) Synthesis of 2-bromo-9,10-diphenyl-9,10-dihydroanthracene-9,10-diol A synthesis scheme of 2-bromo-9,10-diphenyl-9,10-dihydroanthracene-9,10-diol is shown in (C-2). 4.9 g (17 mmol) of 2-bromo-9,10-anthraquinone was put in a 300 mL three-neck flask, the atmosphere in the flask was substituted by nitrogen, and 100 mL of tetrahydrofuran (THF) was added thereto and dissolved well. Then, 18 mL (37 mmol) of phenyllithium was dropped into this solution and stirred at room temperature for about 12 hours. After reaction, the solution was washed with water, and an aqueous layer was extracted with ethyl acetate. The extracted solution and an organic layer were dried with magnesium sulfate. After drying, the mixture was subjected to suction filtration, and the filtrate was concentrated, so that 2-bromo-9,10-diphenyl-9,10-dihydroanthracene-9,10-diol (about 7.6 g) was obtained.

Reference： [1]Current Patent Assignee: IDEMITSU KOSAN CO LTD - WO2006/67931, 2006, A1 Location in patent: Page/Page column 54
[2]Current Patent Assignee: IDEMITSU KOSAN CO LTD - EP1734038, 2006, A1 Location in patent: Page/Page column 42; 46
[3]Current Patent Assignee: SEMICONDUCTOR ENERGY LABORATORY CO.,LTD. - US2009/4506, 2009, A1

15
[ 605-27-6 ]
[ 572-83-8 ]

Yield	Reaction Conditions	Operation in experiment
97%	With bromine In methanol; nitrobenzene	3 EXAMPLE 3 EXAMPLE 3 1265 parts by weight of 2-nitroanthraquinone are reacted at 270° C. with elemental bromine in the presence of 60 parts by weight of nitrobenzene in a laboratory apparatus as described in Example 1. When the reaction is complete, the melt is discharged into 2,000 parts by weight of vigorously stirred methanol at 200° C. The suspension so obtained is refluxed for 1 hour, cooled to 50° C., filtered and dried, affording 1390 g of 2-bromoanthraquinone (97% yield) in 98% purity.

Reference： [1]Current Patent Assignee: H.A. WHITTEN & CO - US4543214, 1985, A

16
[ 572-83-8 ]
[ 2269-22-9 ]
[ 7321-27-9 ]

Yield	Reaction Conditions	Operation in experiment
12.6 g (48%)	With hydrogenchloride; In tetrahydrofuran; cyclohexanol;	EXAMPLES Objects and advantages of this invention are further illustrated by the following examples, but the particular materials and amounts thereof recited in these examples, as well as other conditions and details, should not be construed to unduly limit this invention. Synthesis of 2-bromoanthracene A 1-L, 3-necked flask was fitted with a distillation head and purged with N2. The system was charged with 2-bromoanthraquinone (29.0 g, 101 mmol), cyclohexanol (350 mL), and aluminum tri-sec-butoxide (140 mL, 550 mmol). The mixture was heated and became deep amber as distillate was collected until the pot temperature was 162 C. The reaction was heated at 160 C. for 16 h and then cooled to room temperature. The mixture was mixed with tetrahydrofuran (100 mL) and poured onto a 2 L filter frit to isolate the black solid. The solid was stirred on the frit with 6 M HCl (100 mL) and then further washed with water (500 mL). The gray crude product was air-dried overnight. The solid was purified further by vacuum train sublimation (pressure ~5*10-5 Torr) at a source temperature of 120 C. to afford 12.6 g (48%) of off-white product. DSC data: peak temp 220 C. (DeltaH=126 Jg-1. IR (KBr, strong abs only): 892, 741, 474 cm-1. 1H NMR (500 MHz, d6-Me2SO, internal TMS). delta 7.56 (m, 6 lines, 6-H, 8-H), 7.60 (dd, J=2.0, 9.0 Hz, 7-H), 8.09 (m, 1-H, 3-H, 4-H), 8.39 ('d', J=1 Hz, 9-H), 8.57 (s, 5-H), 8.63 (s, 10-H).

Reference： [1]Patent: US2005/12090,2005,A1

17
ferrocene boronic acid [ No CAS ]
[ 572-83-8 ]
[ 494205-35-5 ]

Yield	Reaction Conditions	Operation in experiment
91%	With potassium carbonate In N,N-dimethyl-formamide under N2, reflux for 20 min, cooling to to room temp., stirring for 2 d; chromy. (neutral alumina, Et2O-petroleum ether (40-60 °C);

Reference： [1]Butler, Ian R.; Caballero, Alfonso G.; Kelly, Glenn A. [Inorganic Chemistry Communications, 2003, vol. 6, # 6, p. 639 - 642]

18
[ 572-83-8 ]
[ 21473-01-8 ]
[ 474688-75-0 ]

Yield	Reaction Conditions	Operation in experiment
	Stage #1: 2-bromoanthracene-9,10-dione; 2-naphthalenylmagnesium bromide In tetrahydrofuran at -78 - 20℃; for 3h; Stage #2: With water; ammonium chloride In tetrahydrofuran	1 Synthesis of Intermediate 1b 10 g of Intermediate 1a (34.8 mmol) was added to 100 ml of THF dried under nitrogen atmosphere, and the temperature of the mixture was decreased to -78° C. 0.5 M of 2-naphthylmagnesiumbromide (10 mmol) was slowly added to the mixture. The temperature of the mixture was increased to room temperature and the mixture was stirred for 3 hours. An aqueous ammonium chloride solution was added to the reacted mixture, and then the resulting product was extracted with methylenechloride. An organic layer was dried using anhydrous MgSO4 and the solvent was removed. The mixture obtained therefrom was dissolved with a small amount of ethylether. Then, petroleum ether was added to the mixture, and stirred for several hours to obtain a solid compound. The obtained solid compound was filtered and then vacuum dried to obtain 17.6 g of dinaphthyl dialcohol.
	In tetrahydrofuran at -78 - 20℃; for 3h;	1 Synthesis of Intermediate 1b; 10 g of Intermediate 1a (34.8 mmol) was added to 100 ml of TNF dried under nitrogen atmosphere, and the temperature of the mixture was decreased to -78°C. 0.5 M of 2-naphthylmagnesiumbromide (10 mmol) was slowly added to the mixture. The temperature of the mixture was increased to room temperature and the mixture was stirred for 3 hours. An aqueous ammonium chloride solution was added to the reacted mixture, and then the resulting product was extracted with methylenechloride. An organic layer was dried using anhydrous MgSO4 and the solvent was removed. The mixture obtained therefrom was dissolved with a small amount of ethylether. Then, petroleum ether was added to the mixture, and stirred for several hours to obtain a solid compound. The obtained solid compound was filtered and then vacuum dried to obtain 17.6 g of dinaphthyl dialcohol.
	Stage #1: 2-bromoanthracene-9,10-dione; 2-naphthalenylmagnesium bromide In tetrahydrofuran at -78 - 20℃; for 3h; Stage #2: With water; ammonium chloride In tetrahydrofuran	1 Synthesis of Intermediate 1b; The intermediate 1 a (10g, 34.8mmol) was added to 100 ml of dried THF under a nitrogen atmosphere. The reaction mixture was cooled to -78° C, and 2-naphthyl magnesium bromide (0.5M, 10 mmol) was gradually added thereto. The reaction solution was heated to room temperature and stirred for three hours. An ammonium chloride solution was added thereto and the resultant solution was extracted with methylenechloride. The organic layer was dried over anhydrous magnesium sulfate to remove the solvent, and dissolved in a trace amount of ethylether. Petroleum ether was added thereto and the reaction mixture was stirred for several hours to obtain a solid compound. The solid compound was filtered and dried under vacuum to yield dinaphthyl dialcohol (17.6g).; The dinaphthyl dialcohol (17.6g, 32.4mmol) was dispersed in 200 ml of acetic acid under a nitrogen atmosphere, and potassium iodide (53.4g, 330mmol) and sodium hypophosphite hydrate (58g, 660mmol) were added thereto. The reaction mixture was stirred and refluxed for three hours. The reaction solution was cooled to room temperature, filtered, washed with water and methanol, and dried under vacuum to yield intermediate 1b as a light yellow powder (11.3g).

Stage #1: 2-bromoanthracene-9,10-dione; 2-naphthalenylmagnesium bromide In tetrahydrofuran at -78 - 20℃; Inert atmosphere; Stage #2: With water; ammonium chloride In tetrahydrofuran

1 Synthesis of Intermediate 1b Synthesis of Intermediate 1b 10 g (34.8 mmol) of Intermediate 1a was added to 100 ml dried tetrahydrofuran (THF) under a nitrogen atmosphere, and the mixture was cooled to - 78°C. Then, 10 mmol of 0. 5M 2-naphthyl magnesium bromide was gradually added thereto. The temperature of the mixture was raised to room temperature and the mixture was stirred for 3 hours. An ammonium chloride solution was added to the mixture and the resulting product was subjected to extraction using methylene chloride. An organic layer was dried using anhydrous magnesium sulfate and the solvent was evaporated. After the resulting product was dissolved in a small amount of ethyl ether, petroleum ether was added thereto and the mixture was stirred for several hours to obtain a solid compound. The solid compound was filtered and dried in a vacuum to obtain 17.6 g of dinaphthyldialcohol.

Reference： [1]Current Patent Assignee: Samsung Display (in: Samsung); SAMSUNG ELECTRONICS CO.,LTD. - US2008/125593, 2008, A1 Location in patent: Page/Page column 10-11
[2]Current Patent Assignee: Samsung Display (in: Samsung); SAMSUNG ELECTRONICS CO.,LTD. - EP1925618, 2008, A1 Location in patent: Page/Page column 15-16
[3]Current Patent Assignee: Samsung Display (in: Samsung); SAMSUNG ELECTRONICS CO.,LTD. - EP1970376, 2008, A1 Location in patent: Page/Page column 12-13
[4]Current Patent Assignee: SAMSUNG ELECTRONICS CO.,LTD.; Samsung Display (in: Samsung) - EP2110373, 2009, A1 Location in patent: Page/Page column 18-19

19
[ 90-11-9 ]
[ 572-83-8 ]
[ 929031-38-9 ]

Yield	Reaction Conditions	Operation in experiment
82%	Stage #1: 1-Bromonaphthalene With n-butyllithium In tetrahydrofuran at -78℃; for 1h; Stage #2: 2-bromoanthracene-9,10-dione In tetrahydrofuran at -78 - 20℃; for 3h;	2.6 1-bromonaphthalene (34.8 g, 168.2 mmol) was dissolved intetrahydrofuran (170 mL) and then cooled to -78 C , n-butyl lithium (67.3 mL, 168.2 mmol) was slowly added thereto, and the agitation wasperformed for 1 hour. 2-bromoanthraquinone (21 g, 73.1 mmol) wasadded thereto and then heated to normal temperature, and the agitationwas performed for 3 hours. The saturated aqueous ammonium chloridesolution was added thereto, the water layer was removed, the drying wasperformed with anhydrous magnesium sulfate, the filtration was performed,and the drying was performed under reduced pressure. Therecrystallization was performed with ethyl ether and petroleum ether toprepare the compound of formula 2-F (32.3 g, 82 %). MS [M+ H]+ = 544
82%	Stage #1: 1-Bromonaphthalene With n-butyllithium In tetrahydrofuran at -78℃; Stage #2: 2-bromoanthracene-9,10-dione In tetrahydrofuran at -78 - 20℃;	105 1-bromonaphthalene (34.8 g, 168 mmol) was dissolved in tetrahydrofuran (170 ml), and cooled to -78C, 2.5 M n-butyl lithium (67.3 ml, 168 mmol) was slowly added thereto, and it was agitated for 1 hour. 2-bromoanthraquinone (21 g, 73.1 mmol) was added, the temperature was increased to normal temperature, and it was agitated for 3 hours. The saturated ammonium chloride aqueous solution was added, the water layer was removed, dried with anhydrous magnesium sulfate, filtered, and dried under reduced pressure. It was recrystallized with ethylether to prepare the compound B-9 (32.5 g, 82%). MS: [M+H]+=544
82%	Stage #1: 1-Bromonaphthalene With n-butyllithium In tetrahydrofuran at -78℃; for 1h; Stage #2: 2-bromoanthracene-9,10-dione In tetrahydrofuran at 20℃; for 3h; Stage #3: With water; ammonium chloride In tetrahydrofuran	2 [Formula 1-B] 1-bromonaphthalene (34.8 g, 168.2 mmol) was dissolved in tetrahydrofurane (170 ml), and cooled to -78°C, n-butyl lithium (67.3 ml, 168.2 mmol) was slowly added thereto, and it was agitated for 1 hour. 2-bromoanthraquinone (21 g, 73.1 mmol) was added, the temperature was increased to normal temperature, and it was agitated for 3 hours. The saturated ammonium chloride aqueous solution was added, the water layer was removed, dried with anhydrous magnesium sulfate, filtered, and dried under reduced pressure. It was recrystallized with ethyl ether and petroleum ether to manufacture the compound of Formula 1-B (32.3 g, 82%). MS: [M+H]+ = 544

82%	Stage #1: 1-Bromonaphthalene With n-butyllithium In tetrahydrofuran for 1h; Stage #2: 2-bromoanthracene-9,10-dione at 20℃; for 3h;	12.1 1) Compound B-9 1-bromonaphthalene (1-bromonaphthalene, 34.8g, 168mmol) was dissolved in tetrahydrofuran (170mL) at -78°C , after the addition of 2.5M n-butyllithium (67.3mL, 168mmol) the temperature was lowered slowly and stirred for 1 hour. 2-bromoanthraquinone (21g, 73.1mmol) was added and stirred at room temperature for 3 hours. Saturated aqueous ammonium chloride solution was added, aqueous layer was dried over anhydrous magnesium sulfate, filtered, concentrated under reduced pressure and recrystallized with ethyl ether to obtain compound B-9 (32.5g, yield 82%) .
60%	Stage #1: 1-Bromonaphthalene With n-butyllithium In tetrahydrofuran at -78℃; for 1h; Inert atmosphere; Stage #2: 2-bromoanthracene-9,10-dione In tetrahydrofuran at -78 - 20℃; Inert atmosphere;	16 Intermediates(5) synthesis of 3 1-bromonaphthalene multi function cap to opening 500 ml (10.8g, 0.05mol) THF and adaptation and agitating the added under nitrogen. Reaction temperature and in -78 ° C n-BuLi (32.6 ml, 0.05mol) is slowly added to the polymerization reaction mixture to visitor is checked through a stirring time 1. 2-bromoanthracene-9 herein, 10-dione (5g, 0.02mol) adding an 4-5 time was reacted at ambient. After reaction is completed, water are added after vacuum distilling a reaction mixture, out by extracting with distilled water and a Methylene Chloride. Extracted Methylene Chloride layer MgSO4after for holding a order to form an exterior, of methanol removing the solvent by the string grudge liquid obtained. An Column Chromatography method using yellow solid(5) separated the. (5.7g, 60%)
60%	Stage #1: 1-Bromonaphthalene With n-butyllithium In tetrahydrofuran at -78℃; for 1h; Inert atmosphere; Stage #2: 2-bromoanthracene-9,10-dione In tetrahydrofuran at 20℃;	16 Synthesis of intermediate (5) Three-necked 500ml flask in 1-bromonaphthalene (10.8g, 0.05mol) and THF were added under nitrogen and stirring. And added slowly to the reaction temperature at -78 n-BuLi (32.6mL, 0.05mol) and stirred 1 hour. To this was added the 2-bromoanthracene-9,10-dione (5g, 0.02mol) and allowed to react at room temperature for 4 to 5 hours. After completion of the reaction, after addition of water, and distilled under reduced pressure, the reaction solution was extracted with Methylene Chloride with distilled water. After japahjun moisture Methylene Chloride the extracted layer with MgSO4, the solvent was removed by distillation under reduced pressure to give a viscous liquid. The liquid using a method Column Chromatography was isolated yellow solid (5). (5.7g, 60%)
45%	Stage #1: 1-Bromonaphthalene With n-butyllithium In tetrahydrofuran at -78℃; for 0.5h; Stage #2: 2-bromoanthracene-9,10-dione In tetrahydrofuran for 2h;	3.1 (1) Synthesis of Compound 2a (2-Bromo-9,10-di-naphthalen-1-yl-9,10-dihydro-anthracene-9,10-diol) 5-Bromo-1,2,3,4-tetrahydro-naphthalene (13.7 mL, 88.0 mmol) was dissolved in anhydrous THF (tetrahydrofuran) (100 mL), the solution was maintained at -78° C. with stirring, and n-BuLi (42.6 mL, 106 mmol) was slowly added dropwise to the solution. After 30 minutes, 2-bromo-9,10-anthraquinone (10.2 g, 35.5 mmol) was added thereto, and the mixture was stirred. After 2 hours, the reaction mixture was washed with a NH4Cl solution, and further twice with distilled water, and then water was removed in anhydrous MgSO4. The solvent was removed with a rotary evaporator. The residue was recrystallized from diethyl ether and petroleum ether to obtain Compound 2a (8.7 g, 45%). Analysis results of this compound are as follows. [0093] 1H NMR (500 MHz, CDCl3) 7.78 (dd, 4H), 7.38 (dd, 4H), 6.82 (dd, 2H), 6.73 (dd, 2H), 6.46 (dd, 2H), 2.60 (t, 4H), 2.37 (t, 4H), 1.64 (m, 8H); MS [M+1-H2O] 526
45%	Stage #1: 1-Bromonaphthalene With n-butyllithium In tetrahydrofuran at -78℃; for 0.5h; Stage #2: 2-bromoanthracene-9,10-dione In tetrahydrofuran for 2h;	3.1 Synthesis of compound 2a (2- bromo-9,10-di - naphthalene-1-yl-9,10- Dihydro - anthracene-9,10-diol) 13.7mL of 5-bromo-1,2,3,4-tetrahydro - naphthalene (88.0mmo) was dissolved in anhydrous THF (tetrahydrofuran, 100mL).while maintaining at -78 , n-BuLi 42.6mL the (106mmol) was slowly added dropwise. After 30 minutes, 2-bromo-9,10-anthraquinone 10.2g (35.5mmol) was added and stirred. After 2 hours, the reaction mixture was washed with NH4Cl solution, 2 with distilled waterAfter further washing times, water was removed with anhydrous MgSO4. Removal of the solvent on a rotary evaporatorIt was removed, and recrystallized from diethyl ether and petroleum ether compound 2a (8.7g, 45%)It was obtained. Analysis results of this compound are as follows.
45%	Stage #1: 1-Bromonaphthalene With n-butyllithium In tetrahydrofuran at -78℃; for 0.5h; Stage #2: 2-bromoanthracene-9,10-dione In tetrahydrofuran at 20℃; for 2h;	1.2 (2) Compound Synthesis of (2-bromo-9,10-di-naphthalene-l-yl-9,10-dihydro-anthracene-9, 10-diol)1-bromonaphthalene of 10.5ml (75.23 mmol) was melted bytetrahydrofuran anhydride of 100ml to be stirred. After maintaining the temperatureat -78 "C, 2.5M N-BuLi of 30ml (75.23 mmol) was dropped slowly. Thirty minuteslater, the mixture was mixed with the compound of 9g (31.34 mmol) to be stirred at room temperatures. The reaction mixture was cleansed by NH4Cl twohours later, extracted by dichloromethane, and water was dried by magnesiumsulfate anhydride. Then, the solvent was removed from the mixture under reducedpressure. The mixture was cleansed by methanol to obtain a following compound (7.7g, 45%).Compound
	Stage #1: 1-Bromonaphthalene With n-butyllithium In tetrahydrofuran at -78℃; for 1.5h; Stage #2: 2-bromoanthracene-9,10-dione In tetrahydrofuran at 20℃; for 24h; Stage #3: With hydrogenchloride In tetrahydrofuran; water	9.9-1 Synthesis Example 9-(1): Synthesis of 2-bromo-9,10-di (1'-naphthyl)anthracene While stirring a 500 ml round bottom flask, 43.3 g (0.209 mol) of 1-naphthylbenzene and 100 ml of (THF) were added. After the temperature was dropped to -78 ° C, 9.1 ml (0.209 mol) of n-BuLi was slowly added dropwise.After the dropwise addition, stir for 1 hour and 30 minutes,2-bromoanthraquinone 20g (0.070mol) was dissolved in THF 100ml and added at high speed.After standing for 10 minutes, the mixture was stirred at room temperature for 1 day.When the reaction was completed, 100 ml of 2N hydrochloric acid was added to make it acidic, and concentrated. The concentrated reaction was placed in a 500 ml round bottom flask and refluxed for 3 hours with 34.69 g (0.209 mol) of KI, 44.30 g (0.418 mol) of NaH2PO2H2O, and 200 ml of acetic acid. Upon completion of the reaction, the mixture was lowered to room temperature, and the resulting solid was filtered, washed with methanol, and recrystallized from toluene. As a result, 25.0 g (0.049 mol, yield 70.5%) of an ocher solid was obtained.

Reference： [1]Current Patent Assignee: LG CHEM CO.,LTD. - WO2008/143440, 2008, A1 Location in patent: Page/Page column 74-75
[2]Current Patent Assignee: LG CHEM CO.,LTD. - EP2311826, 2011, A2 Location in patent: Page/Page column 67
[3]Current Patent Assignee: LG CHEM CO.,LTD. - EP2327679, 2011, A2 Location in patent: Page/Page column 26
[4]Current Patent Assignee: LG CHEM CO.,LTD. - KR101567610, 2015, B1 Location in patent: Paragraph 0223-0225
[5]Current Patent Assignee: WS CO., LTD. - KR101528769, 2015, B1 Location in patent: Paragraph 0188; 0189; 0190; 0191; 0192
[6]Current Patent Assignee: WS CO., LTD. - KR101528767, 2015, B1 Location in patent: Paragraph 0188-0192
[7]Current Patent Assignee: LG CHEM CO.,LTD. - US2014/77165, 2014, A1 Location in patent: Paragraph 0091-0093
[8]Current Patent Assignee: LG CHEM CO.,LTD. - JP5847151, 2016, B2 Location in patent: Paragraph 0069
[9]Current Patent Assignee: DONGJIN SEMICHEM CO.,LTD. - WO2008/140208, 2008, A1 Location in patent: Page/Page column 46-47
[10]Current Patent Assignee: HODOGAYA CHEMICAL CO LTD - KR101553561, 2015, B1 Location in patent: Paragraph 0252-0256

20
[ 572-83-8 ]
[ 76656-50-3 ]

Yield	Reaction Conditions	Operation in experiment
38%	With hydrogenchloride; tin(ll) chloride In water; acetic acid for 5h; Heating / reflux;	2; 3.1 (1) Synthesis of compound <2a>The compound of S.llg (20.1 mmol), tinchloride (SnCl2-H2O) of 13.9Og (61.5 mmol) and 12M hydrochloric acid aqueous solution of 15ml weremelted by acetic acid of 90ml to be refluxed. The mixture was cooled five hourslater, diluted by water, and neutralized by sodium hydrogen carbonate aqueoussolution. After the mixture was extracted by dichloromethane, water was dried bymagnesium sulfate anhydride. After the solvent was removed from the mixtureunder reduced pressure, the solid was purified by column chromatography to obtaina compound <2a> of 2.18g (yield 38%).Compound <2a>

Reference： [1]Current Patent Assignee: DONGJIN SEMICHEM CO.,LTD. - WO2008/140208, 2008, A1 Location in patent: Page/Page column 6; 12-13; 49-50; 92-93

21
[ 57102-42-8 ]
[ 572-83-8 ]
[ 948860-03-5 ]

Yield	Reaction Conditions	Operation in experiment
73%	Stage #1: N-(4-bromophenyl)carbazole With n-butyllithium In tetrahydrofuran; hexane at -78℃; for 0.833333h; Stage #2: 2-bromoanthracene-9,10-dione In tetrahydrofuran; hexane at -78 - 20℃; for 4h;	2.3 The compound of formula 2-B (4.38 g, 13.2 mmol) was dissolved inanhydrous tetrahydrofuran (80 mL) under a nitrogen atmosphere. Thesolution was cooled to ~78 C , n-butyl lithium (6.6 mL, 2.5 M hexanesolution) was slowly added over 10 minutes to the cooled solution, and thesolution was stirred at -78 C for about 40 minutes. 2-bromoanthraquinone compound (3.59 g, 5.5 mmol) was added to thereaction mixture, and the mixture was further stirred at -78 C for about 3hours. The mixture was stirred at room temperature for about 1 hour.To the mixture, an aqueous ammonium chloride solution (50 mL) was added.The organic layer was separated, and the aqueous layer was extractedfrom diethyl ether (60 mL). The combined organic extract was dried overmagnesium sulfate, and concentrated under reduced pressure. Theobtained solid was suspended in diethyl ether, stirred about 1 hour, filtered, and then dried to obtain a compound of formula 2-C (3.32 g, yield 73%),which is a dialcohol compound. MS [M+ H]+ = 773
73%	Stage #1: N-(4-bromophenyl)carbazole With n-butyllithium In tetrahydrofuran; hexane at -78℃; for 0.833333h; Stage #2: 2-bromoanthracene-9,10-dione In tetrahydrofuran; hexane at -78 - 20℃; for 4h;	5.2 2) Synthesis of compound of the following formula 5-B[228] [Formula 5-B][229][230] The compound of the formula 5-A (4.4 g, 13.7 mmol) was dissolved in anhydrous tetrahydrofuran (80 mL) under a nitrogen atmosphere. The solution was cooled to - 78°C, n-butyl lithium (6.6 mL, 2.5 M hexane solution) was slowly added over 10 minutes to the cooled solution, and the solution was stirred at -78°C for about 40 minutes. 2-bromoanthraquinone compound (1.6 g, 5.6 mmol) was added to the reaction mixture, and the mixture was further stirred at -78°C for about 3 hours. The mixture was stirred at room temperature for about 1 hour. To the mixture, an aqueous ammonium chloride solution (50 mL) was added. The organic layer was separated, and the aqueous layer was extracted from diethyl ether (60 mL). The combined organic extract was dried over magnesium sulfate, and concentrated under reduced pressure. The obtained solid was suspended in diethyl ether, stirred about 1 hour, filtered, and then dried to obtain a compound of the formula 5-B (7.7 g, yield 73%), which is a dialcohol compound.
73%	Stage #1: N-(4-bromophenyl)carbazole With n-butyllithium In tetrahydrofuran; hexane at -78℃; for 0.833333h; Inert atmosphere; Stage #2: 2-bromoanthracene-9,10-dione In tetrahydrofuran; hexane at -78 - 20℃; for 4h; Stage #3: With water; ammonium chloride In tetrahydrofuran; hexane	4 The compound of Formula 1-E (4.38 g, 13.2 mmol) was dissolved in dried tetrahydrofurane (80 mL) under the nitrogen atmosphere. The above solution was cooled to -78°C, n-butyl lithium (6.6 mL, 2.5 M hexane solution) was slowly added to the cooled solution for 10 min, and agitated at -78°C for about 40 min. 2-bromoanthraquinone compound (3.59 g, 5.5 mmol) was added to the reaction mixture, and further agitated at -78°C for 3 hours. The mixture was agitated at room temperature for about 1 hour. To the above mixture, aqueous ammonium chloride solution (50 mL) was applied. The organic layer was separated, and the aqueous solution layer was extracted with diethyl ether (60 mL). The extracted organic solution layer was dried with magnesium sulfate and concentrated under the reduced pressure. The obtained solid was suspended with diethyl ether, agitated for 1 hour, and filtered. After the drying, the compound of Formula 1-F (3.32 g, 73%) that was the dialcohol compound was manufactured. MS: [M+H] + = 774

Reference： [1]Current Patent Assignee: LG CHEM CO.,LTD. - WO2008/143440, 2008, A1 Location in patent: Page/Page column 71-73
[2]Current Patent Assignee: LG CHEM CO.,LTD. - WO2007/102683, 2007, A1 Location in patent: Page/Page column 48-49
[3]Current Patent Assignee: LG CHEM CO.,LTD. - EP2327679, 2011, A2 Location in patent: Page/Page column 27

22
[ 109-72-8 ]
2H₂O [ No CAS ]
[ 580-13-2 ]
[ 124-38-9 ]
[ 572-83-8 ]
[ 474688-76-1 ]

Yield	Reaction Conditions	Operation in experiment
	With hydrogenchloride; stannous chloride; In tetrahydrofuran; acetic acid; acetone;	Synthesis of 2-Bromo-9,10-di(naphthalen-2-yl)anthracene 4.3 g (21 mmole) of 2-bromonaphthalene was placed in an 100 ml round bottom flask, and was dissolved in dry THF. The solution was cooled down to 31 70 C. by dry-ice/acetone, then 1.6M n-Butyllithium 13 ml (21 mmole) was added slowly over 30 minutes. The reaction was stirred for 2 hours while the reaction temperature was maintained at -70 C., 2-bromoanthraquinone 2 g (6.9 mmole; manufactured by Tokyo Chemical Industry Co., LTD.,) was added to the cooled reaction mixture, the reaction was stirred for overnight at room temperature. Then, 30 ml of 10% HCl was added to the resulting solution, and stirred for 30 minutes, the organic layer was separated, and was evaporated to dryness, the brown color residue was dissolved in 50 ml of acetic acid, and 1.6 g of SnCl2. 2H2O were added to the brown solution. The reaction mixture was heated to reflux for 6 hours, and then, cooled down to room temperature. Thus, the Brown product was collect by filtration. (2.47 g, 70.4%)

Reference： [1]Patent: US2008/299294,2008,A1

23
[ 7789-45-9 ]
[ 117-79-3 ]
[ 572-83-8 ]

Yield	Reaction Conditions	Operation in experiment
58%	With hydrogenchloride; tert.-butylnitrite In toluene; acetonitrile	1.i (i) (i) Synthesis of 2-bromo-9,10-anthraquinone A synthesis scheme of 2-bromo-9,10-anthraquinone is represented by (C-1). 46 g (0.20 mol) of copper(II) bromide and 500 mL of acetonitrile were put in a 1 L three-neck flask. Further, 17 g (0.17 mol) of tert-butyl nitrite was added thereto, and the mixture was heated to 65° C. 25 g (0.11 mol) of 2-amino-9,10-anthraquinone was added to the mixture and stirred for six hours at the same temperature. After reaction, the reaction solution was poured into 500 mL of hydrochloric acid (3 mol/L) and this suspension was stirred for three hours, so that a solid substance was precipitated. The precipitation was collected by suction filtration and washed with water and ethanol while being subjected to suction filtration. The residue was dissolved in toluene and was subjected to suction filtration through Florisil (manufactured by Floridin Company), Celite (manufactured by Celite Co., Ltd.), and alumina, and the filtrate was obtained. The obtained filtrate was concentrated, so that a solid substance was obtained. The obtained solid substance was recrystallized with a mixed solvent of chloroform and hexane, so that 18.6 g of a milky white powdered solid substance, 2-bromo-9,10-anthraquinone was obtained in 58% yield.
58%	With tert.-butylnitrite In hexane; chloroform; toluene; acetonitrile	1.1 Step 1: Step 1: Synthesis of 2-bromo-9,10-anthraquinone Into a 1 L three-neck flask were put 46 g (206 mmol) of copper(II) bromide and 500 mL of acetonitrile, and 17.3 g (168 mmol) of tert-butyl nitrite was added thereto. While this mixture was heated at 65° C., 25 g (111 mmol) of 2-amino-9,10-anthraquinone was added to the mixture. This mixture was stirred for six hours at the same temperature. After the stirring, this reaction solution was poured into approximately 500 mL (3.0 mol/L) of hydrochloric acid and this mixture was stirred for three hours. After the stirring, the mixture including precipitate was filtered and the residue was washed with water and ethanol. After the washing, the residue was dissolved in toluene and this solution was subjected to suction filtration through Florisil (produced by Wako Pure Chemical Industries, Ltd., Catalog No. 540-00135), Celite (produced by Wako Pure Chemical Industries, Ltd., Catalog No. 531-16855), and alumina. The obtained filtrate was concentrated, so that a solid substance was obtained. The obtained solid substance was recrystallized with a mixed solution of chloroform/hexane to give 18.6 g of a light-yellow powdered solid substance, 2-bromo-9,10-anthraquinone, which was the target matter of the synthesis, in 58% yield. The synthesis scheme of Step 1 is shown in (B-1).

Reference： [1]Current Patent Assignee: SEMICONDUCTOR ENERGY LABORATORY CO.,LTD. - US2009/4506, 2009, A1
[2]Current Patent Assignee: SEMICONDUCTOR ENERGY LABORATORY CO.,LTD. - US2009/267497, 2009, A1

24
[ 2052-07-5 ]
[ 572-83-8 ]
[ 474688-70-5 ]

Yield	Reaction Conditions	Operation in experiment
94%	Stage #1: 2-Bromobiphenyl With tert.-butyl lithium In tetrahydrofuran; pentane at -78℃; for 1h; Stage #2: 2-bromoanthracene-9,10-dione In tetrahydrofuran; pentane at -78 - 20℃; for 3h;	5 Synthesis of Compound 1052-Bromo biphenyl (9.0 mL, 52 mmol) was dissolved in dried tetrahydrofuran (100 mL) under a nitrogen atmosphere at room temperature. The solution was cooled to -78° C. in a cooling bath, and t-butyl lithium (40 mL, 1.7 M pentane solution) was slowly added thereto. After stirring at the same temperature for 1 hour, Compound 104 (4.9 g, 17 mmol) was added to the mixture. The cooling bath was removed, and the mixture was stirred for about 3 hours at room temperature. Aqueous ammonium chloride solution was added to the mixture, which was then extracted with methylene chloride. The organic extract was dried over magnesium sulfate and concentrated under reduced pressure. The concentrated solid was dispersed in ethanol, which was stirred for 1 hour, filtered off with suction, and washed with ethanol. After drying, Compound 105 (9.50 g, 94%) was obtained.
94%	Stage #1: 2-Bromobiphenyl With tert.-butyl lithium In tetrahydrofuran; pentane at -78℃; for 1h; Stage #2: 2-bromoanthracene-9,10-dione In tetrahydrofuran; pentane at -78 - 20℃; for 3h; Stage #3: With ammonium chloride In tetrahydrofuran; water; pentane	5 2-Bromo biphenyl (9.0 mL, 52 mmol) was dissolved in dried tetrahydrofuran (100 mL) under a nitrogen atmosphere at room temperature. The solution was cooled to-78°C in a cooling bath, and t-butyl lithium (40 mL, 1.7 M pentane solution) was slowly added thereto. After stirring at the same temperature for 1 hour, Compound 104 (4.9 g, 17 mmol) was added to the mixture. The cooling bath was removed, and the mixture was stirred for about 3 hours at room temperature. Aqueous ammonium chloride solution was added to the mixture, which was then extracted with methylene chloride. The organic extract was dried over magnesium sulfate and concentrated under reduced pressure. The concentrated solid was dispersed in ethanol, which was stirred for 1 hour, filtered off with suction, and washed with ethanol. After drying, Compound 105 (9.50 g, 94%) was obtained.
94%	Stage #1: 2-Bromobiphenyl With tert.-butyl lithium In tetrahydrofuran; pentane at -78℃; for 1h; Inert atmosphere; Stage #2: 2-bromoanthracene-9,10-dione In tetrahydrofuran; pentane Stage #3: With ammonium chloride In tetrahydrofuran; water; pentane	5 Preparation Example 5 (Preparation of starting material represented by the Chemical Formula e) [0047] 2-Bromo biphenyl (9.0 mL, 52 mmol) was dissolved in dried tetrahydrofuran (100 mL) under a nitrogen atmosphere, and t-butyl lithium (40 mL, 1.7 M pentane solution) was slowly added at -78°C. After stirring at the same temperature for 1 hour, the compound of the Chemical Formula d prepared in Preparation Example 4 (4.9 g, 17 mmol) was added. Aqueous ammonium chloride solution was added to the mixture, and then it was extracted with methylene chloride. The organic extract was dried over magnesium sulfate and concentrated under reduced pressure. The obtained solid was dispersed in ethanol, stirred for 1 hour, filtered off with suction, and washed with ethanol. After drying, a compound of the Chemical Formula e (9.50 g, 94%) was obtained.

92%	Stage #1: 2-Bromobiphenyl With tert.-butyl lithium In tetrahydrofuran; pentane at -78℃; for 0.666667h; Stage #2: 2-bromoanthracene-9,10-dione In tetrahydrofuran; pentane at -78 - 20℃; for 3h;	1 To a solution of 2-bromobiphenyl (9.00 ml, 52.0 mmol) in THF (100 ml) was added dropwise t-BuLi (40 ml of a 1.7 M solution in pentane) at -78° C. under nitrogen. After the mixture had been stirred for 40 min, 2-bromoanthraquinone (5.00 g, 17.0 mmol) was added at -78° C. The cooling bath was removed and the mixture was stirred for 3 hours at room temperature. The reaction mixture was poured into diethyl ether (150 ml) and 2 N HCl (150 ml), and stirred for 40 min at room temperature. The precipitate was filtered off with suction, washed with water and ethyl ether, and then dried to obtain 2-bromo-9,10-bis(2-biphenyl-hydroxy)-anthracene (9.50 g, 92%).
	Stage #1: 2-Bromobiphenyl With alkyl lithium In tetrahydrofuran; pentane at -78℃; for 0.666667h; Inert atmosphere; Stage #2: 2-bromoanthracene-9,10-dione In tetrahydrofuran; pentane at -78 - 20℃; for 3h; Inert atmosphere;	A Preparation A: Preparation of intermediate compound A In a 500 mL round bottom flask in a nitrogen atmosphere, 2-bromobiphenyl (2.68 g, 11.5 mmol) of the compound y-1 was dissolved in 35 ml of THF, cooled to -78°C, and tert-butyllithium (t-BuLi) 16.9 ml (1.7 M in pentane) was added dropwise and then stirred at the same temperature for 40 minutes. After adding 2-bromoanthraquinone, compound x-1, to the prepared solution, the temperature was gradually raised to room temperature and stirred for 3 hours. Thereafter, the reactant was poured into a mixed solution of 15 ml of diethyl ether and 25 ml of 2N hydrochloric acid aqueous solution, stirred for 30 minutes, and the resulting solid was filtered, washed with water and diethyl ether, and dried. 2.5 g of the dried solid sample was taken and dissolved in 50 ml of acetic acid, and then a catalytic amount (10 drops) of concentrated sulfuric acid was added and refluxed for 3 hours. Thereafter, the resulting solid compound was filtered, washed with acetic acid, and dried to obtain a white solid compound A-1 (2.2 g, yield: 79%).
	Stage #1: 2-Bromobiphenyl With butyllithium In tetrahydrofuran; pentane at -78℃; for 0.666667h; Inert atmosphere; Stage #2: 2-bromoanthracene-9,10-dione In tetrahydrofuran; pentane at 20℃; for 3h;	Preparation A: Preparation of intermediate compound A In a nitrogen atmosphere, in a 500 mL round bottom flask, compound y-1, 2-bromobiphenyl (2.68 g, 11.5 mmol) was dissolved in 35 ml of THF,After cooling to -78°C tert-Butyllithium (t-BuLi) 16.9 ml (1.7 M in pentane)was added dropwise and stirred at the same temperature for 40 minutes.After adding 2-bromoanthraquinone as compound x-1 to the prepared solution, the temperature was slowly raised to room temperature and stirred for 3 hours.Thereafter, the reaction product was poured into a mixed solution of 15 ml of diethyl ether and 25 ml of 2N aqueous hydrochloric acid, stirred for 30 minutes, and the resulting solid was filtered,After washing with water and diethyl ether, it was dried. 2.5 g of the dried solid sample was taken and dissolved in 50 ml of acetic acid, and then a catalytic amount (10 drops) of concentrated sulfuric acid was added and refluxed for 3 hours. Thereafter, the resulting solid compound was filtered, washed with acetic acid, and dried to obtain an intermediate compound A (2.2 g, yield: 79%) as a white solid compound.

Reference： [1]Current Patent Assignee: LG CHEM CO.,LTD. - US7485733, 2009, B2 Location in patent: Page/Page column 75
[2]Current Patent Assignee: LG CHEM CO.,LTD. - WO2003/95445, 2003, A1 Location in patent: Page/Page column 70-71
[3]Current Patent Assignee: LG CHEM CO.,LTD. - EP1465874, 2004, A2 Location in patent: Paragraph 0047
[4]Current Patent Assignee: LG CHEM CO.,LTD. - US6998487, 2006, B2 Location in patent: Page/Page column 44
[5]Current Patent Assignee: LG CHEM CO.,LTD. - KR2021/46484, 2021, A Location in patent: Paragraph 0203-0205
[6]Current Patent Assignee: LG CHEM CO.,LTD. - KR2021/46920, 2021, A Location in patent: Paragraph 0235-0238

25
[ 29488-24-2 ]
[ 572-83-8 ]
[ 624744-61-2 ]

Yield	Reaction Conditions	Operation in experiment
82%		Synthesis of Compound 113Compound 111 (1.00 g, 4.18 mmol) was dissolved in dried tetrahydrofuran (30 mL) at room temperature under a nitrogen atmosphere. The solution then was cooled to -78 C. in a cooling bath, and t-butyl lithium (3.3 mL, 1.7 M pentane solution) was slowly added to the solution at that temperature. The mixture was stirred for about 1 hour at the same temperature, and Compound 104 (0.4 g, 1.4 mmol) was added thereto. After stirring for 30 minutes at -78 C., the cooling bath was removed, and the mixture was further stirred for about 3 hours at room temperature. The mixture was quenched with 1 N HCl (50 ml) and extracted with diethyl ether. The organic layer was dried over magnesium sulfate and concentrated in vacuo. The crude product was slurried in petroleum ether, filtered off with suction, and dried to obtain Compound 113 (0.70 g, 82%).
82%		Compound 111 (1.00 g, 4.18 mmol) was dissolved in dried tetrahydrofuran (30 mL) at room temperature under a nitrogen atmosphere. The solution then was cooled to-78C in a cooling bath, and t-butyl lithium (3.3 mL, 1.7 M pentane solution) was slowly added to the solution at that temperature. The mixture was stirred for about 1 hour at the same temperature, and Compound 104 (0.4 g, 1.4 mmol) was added thereto. After stirring for 30 minutes at-78C, the cooling bath was removed, and the mixture was further stirred for about 3 hours at room temperature. The mixture was quenched with 1 N HCl (50 ml) and extracted with diethyl ether. The organic layer was dried over magnesium sulfate and concentrated in vacuo. The crude product was slurried in petroleum ether, filtered off with suction, and dried to obtain Compound 113 (0.70 g, 82%).

Reference： [1]Patent: US7485733,2009,B2 .Location in patent: Page/Page column 77
[2]Patent: WO2003/95445,2003,A1 .Location in patent: Page/Page column 73-74

26
[ 580-13-2 ]
[ 572-83-8 ]
[ 474688-75-0 ]

Yield	Reaction Conditions	Operation in experiment
94%	Stage #1: 2-bromonaphthalene With tert.-butyl lithium In tetrahydrofuran; pentane at -78℃; for 1h; Inert atmosphere; Stage #2: 2-bromoanthracene-9,10-dione In tetrahydrofuran; pentane at -78 - 20℃; for 3h;	9 Preparation Example 9 (Preparation of starting material represented by Chemical Formula i) 2-Bromonaphthalene (11.0 g, 53.1 mmol) was dissolved in dry tetrahydrofuran (100 mL) under a nitrogen atmosphere, and t-butyllithium (47.0 mL, 1.7 pentane solution) was slowly added at -78°C. After agitating at the same temperature for 1 hour, the compound of the Chemical Formula d prepared in Preparation Example 4 (6.31 g, 22.0 mmol) was added. The cooling bath was removed and the reaction mixture was stirred at room temperature for 3 hours. After adding an aqueous ammonium chloride solution to the reaction mixture, the reaction mixture was extracted with methylene chloride. The organic extract was dried over magnesium sulfate and concentrated under reduced pressure. The crude product was dissolved in diethyl ether, and then petroleum ether was added and the mixture was agitated for several hours to obtain a solid compound. The solid was filtered and vacuum dried to obtain dinaphthyl dialcohol (11.2 g, 94%). Dinaphthyl dialcohol, synthesized above, (11.2 g, 20.6 mmol) was dispersed in 600 mL of acetic acid under a nitrogen atmosphere, and then potassium iodide (34.2 g, 206 mmol) and sodium hypophosphite hydrate (36.0 g, 340 mmol) were added, and the mixture was agitated while boiling for 3 hours.
93%	Stage #1: 2-bromonaphthalene With tert.-butyl lithium In tetrahydrofuran; pentane at -78℃; for 1h; Stage #2: 2-bromoanthracene-9,10-dione In tetrahydrofuran; pentane at -78 - 20℃; for 3h;	9 Synthesis of Compound 109 Synthesis of Compound 1092-Bromonaphthalene (11.0 g, 53.1 mmol) was dissolved in dry tetrahydrofuran (100 mL) under a nitrogen atmosphere at room temperature. The solution was cooled to -78° C. in a cooling bath, and t-butyllithium (47.0 mL, 1.7 pentane solution) was slowly added thereto. The mixture was stirred at the same temperature for about 1 hour, and Compound 104 (6.31 g, 22.0 mmol) was added thereto still at the same temperature. Then the cooling bath was removed, and the mixture was stirred at room temperature for about 3 hours. To the stirred mixture an aqueous ammonium chloride solution was added. The resulting mixture was extracted with methylene chloride. The organic extract was dried over magnesium sulfate and concentrated under reduced pressure. The crude product was dissolved in diethyl ether, and then petroleum ether was added thereto. The mixture was agitated for several hours to obtain a solid compound. The solid was filtered and vacuum dried to obtain dinaphthyl dialcohol (11.2 g, 93%). The dinaphtyl dialcohol (11.2 g, 20.5 mmol) was dispersed in 600 mL of acetic acid under a nitrogen atmosphere, to which potassium iodide (34.2 g, 206 mmol) and sodium hypophosphite hydrate (36.0 g, 340 mmol) were added. The resulting mixture was agitated while boiling for about 3 hours. After cooling to room temperature, the mixture was filtered and washed with water and methanol, and then vacuum dried to obtain Compound 109 (10.1 g, 96%) a light yellow color.
93%	Stage #1: 2-bromonaphthalene With tert.-butyl lithium In tetrahydrofuran; pentane at -78℃; for 1h; Stage #2: 2-bromoanthracene-9,10-dione In tetrahydrofuran; pentane at -78 - 20℃; for 3h; Stage #3: With ammonium chloride In tetrahydrofuran; water; pentane	9 2-Bromonaphthalene (11.0 g, 53.1 mmol) was dissolved in dry tetrahydrofuran (100 mL) under a nitrogen atmosphere at room temperature. The solution was cooled to-78°C in a cooling bath, and t-butyllithium (47.0 mL, 1.7 pentane solution) was slowly added thereto. The mixture was stirred at the same temperature for about 1 hour, and Compound 104 (6.31 g, 22.0 mmol) was added thereto still at the same temperature. Then the cooling bath was removed, and the mixture was stirred at room temperature for about 3 hours. To the stirred mixture an aqueous ammonium chloride solution was added. The resulting mixture was extracted with methylene chloride. The organic extract was dried over magnesium sulfate and concentrated under reduced pressure. The crude product was dissolved in diethyl ether, and then petroleum ether was added thereto. The mixture was agitated for several hours to obtain a solid compound. The solid was filtered and vacuum dried to obtain dinaphthyl dialcohol (11.2 g, 93%). The dinaphtyl dialcohol (11.2 g, 20.5 mmol) was dispersed in 600 mL of acetic acid under a nitrogen atmosphere, to which potassium iodide (34.2 g, 206 mmol) and sodium hypophosphite hydrate (36.0 g, 340 mmol) were added. The resulting mixture was agitated while boiling for about 3 hours. After cooling to room temperature, the mixture was filtered and washed with water and methanol, and then vacuum dried to obtain Compound 109 (10.1 g, 96%) a light yellow color.

93%	Stage #1: 2-bromonaphthalene With tert.-butyl lithium In tetrahydrofuran; pentane at -78℃; for 0.5h; Stage #2: 2-bromoanthracene-9,10-dione In tetrahydrofuran; pentane at -78 - 20℃; for 2h;	16 To a solution of 2-bromonaphthalene (6.49 g, 31.3 mmol) in dry THF (50 ml) was added dropwise t-BuLi (18.4 ml of a 1.7 M solution in pentane) at -78° C. under nitrogen. After the mixture had been stirred for 30 min, 2-bromoanthraquinone (3.00 g, 10.4 mmol) was added at -78° C. The cooling bath was removed and the mixture was stirred for 2 hours at room temperature. The mixture was quenched with saturated aqueous ammonium chloride solution (50 ml) and extracted with ethyl ether (3*50 ml). The combined organic extracts were dried over MgSO4 and concentrated under vacuum. The crude product was slurried in petroleum ether, filtered off with suction, and washed with petroleum ether. After drying, the 2-bromo-9,10-di-naphthalene-2-yl-9,10-dihydro-anthracene-9,10-diol (5.30 g, 93%) was obtained.
93%	Stage #1: 2-bromonaphthalene With n-butyllithium In tetrahydrofuran; pentane at -78℃; for 1h; Stage #2: 2-bromoanthracene-9,10-dione In tetrahydrofuran; pentane at 20℃; for 3h;	1.1-B 1-B. Production of compound Ib; [62] 2-bromonaphthalene (11.0 g, 53.1 mmol) was dissolved in THF (100 mL) that was dried in a nitrogen atmosphere, t-butyl lithium (46.8 mL, a 1.7M pentane solution) was slowly added thereto at -780C, agitation was performed at the same temperature for 1 hour, and the compound Ia (6.36 g, 22.0 mmol) was added. After the cooling vessel was removed, agitation was performed at normal temperature for 3 hours. After an ammonium chloride aqueous solution was added to the reaction mixture, extraction was performed by using methylene chloride. The organic layer was dried by using anhydrous magnesium sulfate and the solvent was removed. After the obtained mixture was dissolved in a small amount of ethyl ether, petroleum ether was added and agitation was performed for several hours to obtain a solid compound. The solid compound was filtered and then subjected to vacuum drying to obtain a compound Ib (11.2 g, 93%).[63] MS [M] = 543
58%	Stage #1: 2-bromonaphthalene With n-butyllithium In tetrahydrofuran at -78℃; for 1h; Inert atmosphere; Stage #2: 2-bromoanthracene-9,10-dione In toluene at -78 - 20℃; Inert atmosphere;	17 Intermediates(7) synthesis of 3 2-bromonaphthalene multi function cap to opening 500 ml (10.8g, 0.05mol) THF and adaptation and agitating the added under nitrogen. Reaction temperature and in -78 ° C n-BuLi (32.6 ml, 0.05mol) is slowly added to the polymerization reaction mixture to visitor is checked through a stirring time 1. 2-bromoanthracene-9 herein, 10-dione (5g, 0.02mol) adding an 4-5 time was reacted at ambient. After reaction is completed, water are added after vacuum distilling a reaction mixture, out by extracting with distilled water and a Methylene Chloride. Extracted Methylene Chloride layer MgSO4after for holding a order to form an exterior, of methanol removing the solvent by the string grudge liquid obtained. An Column Chromatography method using yellow solid(7) separated the. (5.5g, 58%)
58%	Stage #1: 2-bromonaphthalene With n-butyllithium In tetrahydrofuran at -78℃; for 1h; Inert atmosphere; Stage #2: 2-bromoanthracene-9,10-dione In tetrahydrofuran at 20℃;	17 Synthesis of intermediate (7) Three-necked 500ml flask to 2-bromonaphthalene (10.8g, 0.05mol) and THF were added under nitrogen and stirring. And added slowly to the reaction temperature at -78 n-BuLi (32.6mL, 0.05mol) and stirred 1 hour. To this was added the 2-bromoanthracene-9,10-dione (5g, 0.02mol) and allowed to react at room temperature for 4 to 5 hours. After completion of the reaction, after addition of water, and distilled under reduced pressure, the reaction solution was extracted with Methylene Chloride with distilled water. After japahjun moisture Methylene Chloride the extracted layer with MgSO4, the solvent was removed by distillation under reduced pressure to give a viscous liquid. The liquid using a method Column Chromatography was isolated yellow solid (7). (5.5g, 58%)
	Stage #1: 2-bromonaphthalene With n-butyllithium In tetrahydrofuran; hexane at -78℃; for 2h; Inert atmosphere; Stage #2: 2-bromoanthracene-9,10-dione In tetrahydrofuran; hexane at -78 - 25℃; Inert atmosphere; Stage #3: With ammonium chloride In tetrahydrofuran; hexane; water	5 Preparation of Compound (130)Under nitrogen atmosphere, 2-bromonaphthalene (27.3 g, 132 mmol) was dissolved in tetrahydrofuran (250 mL), and n-BuLi (2.5 M in n-hexane) (79.2 mL, 198 mmol) was added dropwise at -78° C. thereto. After stirring for 2 hours, the reaction mixture was slowly added dropwise at -78° C. to a solution of 2-bromoanthraquinone (Compound III) (12.6 g, 44 mmol) dissolved in tetrahydrofuran (200 mL) at 25° C. under nitrogen atmosphere. The temperature was slowly raised from -78° C. to 25° C., and the reaction mixture was stirred for 12 hours. After quenching the reaction by adding saturated aqueous ammonium chloride solution (200 mL), the reaction mixture was extracted with ethyl acetate (200 mL) and dried over anhydrous magnesium sulfate. Evaporation of the organic layer under reduced pressure and recrystallization from dichloromethane (200 mL) gave Compound (130) (20.0 g, 36.8 mmol).
	Stage #1: 2-bromonaphthalene With n-butyllithium In tetrahydrofuran at -78℃; for 1h; Stage #2: 2-bromoanthracene-9,10-dione In tetrahydrofuran at 20℃; for 12h; Stage #3: With hydrogenchloride In tetrahydrofuran; water	3.3-1 Synthesis Example 3: Synthesis of Compound 16 3-1) Synthesis of 2-bromo-9,10-di(2-naphthyl)anthracene 360 g (1.74 mol) of bromonaphthalene was dissolved with THF in a 5L flask and the temperature was lowered to -78°C and 1600 ml (1.6 mol) of 1.6M n-BuLi was slowly added dropwise thereto. The mixture was stirred for one hour, and then 200 g (0.68 mol) of 2-bromoanthraquinone was added thereto in a solid state and then the temperature was slowly raised to room temperature and the resultant mixture was stirred. After 12 hours, 500 ml of 2N HCl(aq) was added thereto. Then, an organic layer was isolated and dried over MgSO4 and condensed under reduced pressure, thereby producing Compound C. The Compound C was used in the subsequent reaction without purification. Compound C, 346 g (2.09 mol) of KI, and 443 g (4.1 mol) of NaH2PO2-H2O were diluted with an acetic acid and then the mixture was refluxed while heating. The temperature was lowered to room temperature and thus a solid was precipitated. The solid was filtered, washed with excess water and MeOH, and re-crystallized with 300 ml of toluene, thereby producing 2-bromo-9,10-di(2-naphthyl)anthracene (230 g, 64%).
	Stage #1: 2-bromonaphthalene With n-butyllithium In tetrahydrofuran at -78℃; Stage #2: 2-bromoanthracene-9,10-dione In tetrahydrofuran at -40℃; for 12h;
	Stage #1: 2-bromonaphthalene With n-butyllithium In tetrahydrofuran at -78℃; for 1.5h; Stage #2: 2-bromoanthracene-9,10-dione In tetrahydrofuran at 20℃; for 24h; Stage #3: With hydrogenchloride In tetrahydrofuran; water	5.5-1 Synthesis 5-(1): Synthesis of 2-bromo-9,10-di(2'-naphthyl) anthracene 43.3 g (0.209) of 2-naphthylbenzene while stirring a 500 ml round bottom flaskmol) and 100 ml of THF.After the temperature was dropped to -78 ° C, 9.1 ml (0.209 mol) of n-BuLi was slowly added dropwise. After the dropwise addition, stir for 1 hour and 30 minutes,20 g (0.070 mol) of 2-bromoanthraquinoneIt was dissolved in 100 ml and added at a high speed.After standing for 10 minutes, the mixture was stirred at room temperature for 1 day.When the reaction was completed, 100 ml of 2N hydrochloric acid was added to make it acidic, and concentrated.The concentrated reaction was placed in a 500 ml round bottom flask and refluxed for 3 hours with 34.69 g (0.209 mol) of KI, 44.30 g (0.418 mol) of NaH2PO2H2O, and 200 ml of acetic acid. Upon completion of the reaction, the mixture was lowered to room temperature, and the resulting solid was filtered, washed with methanol, and recrystallized from toluene. As a result, 18.0 g (0.043 mol, yield 61.6%) of an ocher solid was obtained.

Reference： [1]Current Patent Assignee: LG CHEM CO.,LTD. - EP1465874, 2004, A2 Location in patent: Paragraph 0051
[2]Current Patent Assignee: LG CHEM CO.,LTD. - US7485733, 2009, B2 Location in patent: Page/Page column 76
[3]Current Patent Assignee: LG CHEM CO.,LTD. - WO2003/95445, 2003, A1 Location in patent: Page/Page column 72
[4]Current Patent Assignee: LG CHEM CO.,LTD. - US6998487, 2006, B2 Location in patent: Page/Page column 51
[5]Current Patent Assignee: LG CHEM CO.,LTD. - WO2008/13399, 2008, A1 Location in patent: Page/Page column 13
[6]Current Patent Assignee: WS CO., LTD. - KR101528769, 2015, B1 Location in patent: Paragraph 0199; 0200; 0201; 0202; 0203
[7]Current Patent Assignee: WS CO., LTD. - KR101528767, 2015, B1 Location in patent: Paragraph 0199-0203
[8]Current Patent Assignee: DOW INC - US2011/54228, 2011, A1 Location in patent: Page/Page column 12
[9]Current Patent Assignee: SAMSUNG ELECTRONICS CO.,LTD.; Samsung Display (in: Samsung) - EP2292604, 2011, A2 Location in patent: Page/Page column 24
[10]Location in patent: experimental part Shin, Min-Gi; Kim, Seul Ong; Park, Hyun Tae; Park, Sung Jin; Yu, Han Sung; Kim, Yun-Hi; Kwon, Soon-Ki [Dyes and Pigments, 2012, vol. 92, # 3, p. 1075 - 1082]
[11]Current Patent Assignee: HODOGAYA CHEMICAL CO LTD - KR101553561, 2015, B1 Location in patent: Paragraph 0198-0203

27
[ 117-79-3 ]
2-bromo-9,10-anthracene [ No CAS ]
[ 572-83-8 ]

Yield	Reaction Conditions	Operation in experiment
58%	With hydrogenchloride; tert.-butylnitrite In copper(II)bromide; toluene; acetonitrile	1.i EXAMPLE 1 (i) Synthesis of 2-Bromo-9,10-anthraquinone A synthesis scheme of 2-bromo-9,10-anthraquinone is illustrated in (C-1). In a IL three-neck flask were put 46 g (206 mmol) of copper(II) bromide and 500 mL of acetonitrile. To the mixture was added 17.3 g (168 mmol) of tert-butyl nitrite. This mixture was heated to 65° C. While the mixture was heated, to this mixture was added 25 g (111 mmol) of 2-amino-9,10-anthraquinone. This mixture was stirred at the same temperature for 6 hours. Then, this solution was poured into about 500 niL of hydrochloric acid (3 mol/L). This mixture was stirred for 3 hours. Then, the solid precipitated from the mixture was filtered off. The obtained residue was washed with water and ethanol. Then, the residue was dissolved in toluene, and this solution was suction filtered through Florisil (a product of Wako Pure Chemical Industries, Ltd., Catalog No. 540-00135), Celite (a product of Wako Pure Chemical Industries, Ltd., Catalog No. 531-16855), and alumina. The obtained filtrate was concentrated to give a solid. The solid was recrystallized with chloroform/hexane to give 2-bromo-9,10-anthracene, which was the object of the synthesis, as 18.6 g of a light yellow powdered solid in a yield of 58%.

Reference： [1]Current Patent Assignee: SEMICONDUCTOR ENERGY LABORATORY CO.,LTD. - US2009/267498, 2009, A1

28
[ 572-83-8 ]
[ 103068-20-8 ]
[ 474688-78-3 ]

Yield	Reaction Conditions	Operation in experiment
74%	Stage #1: 1-bromo-3,5-diphenylbenzene With tert.-butyl lithium In tetrahydrofuran; pentane at -78℃; for 0.5h; Stage #2: 2-bromoanthracene-9,10-dione In tetrahydrofuran; pentane at -78 - 20℃; for 2h;	18 To a solution of 3,5-(diphenyl)bromobenzene (5.00 g, 16.2 mmol) in dry THF (50 ml) was added dropwise t-BuLi (9.53 ml of a 1.7 M solution in pentane) at -78° C. under nitrogen. After the mixture had been stirred for 30 min, 2-bromoanthraquinone (1.55 g, 5.39 mmol) was added at -78° C. The cooling bath was removed and the mixture was stirred for 2 hours at room temperature. The mixture was quenched with saturated aqueous ammonium chloride solution (50 ml) and extracted with ethyl ether (3*50 ml). The combined organic extracts were dried over MgSO4 and concentrated under vacuum. The crude product was slurried in petroleum ether, filtered off with suction, and washed with petroleum ether. After drying, 2-bromo-9,10-[1,1',3',1"]terphenyl-5'-yl-9,10-dihydro-anthracene-9,10-diol (3.00 g, 74%) was obtained.

Reference： [1]Current Patent Assignee: LG CHEM CO.,LTD. - US6998487, 2006, B2 Location in patent: Page/Page column 52

29
[ 29786-93-4 ]
[ 572-83-8 ]
[ 88020-03-5 ]
[ 1244370-26-0 ]

Yield	Reaction Conditions	Operation in experiment
79%	Stage #1: n-butyllithium; 4-n-dodecylphenylacetylene In tetrahydrofuran; hexane at 0℃; for 1h; Stage #2: 2-bromoanthracene-9,10-dione In tetrahydrofuran; hexane at 20℃; for 8h; Stage #3: With tin(II)chloride dihydrate In tetrahydrofuran; water at 20℃;

Reference： [1]Location in patent: experimental part Cui, Weibin; Fu, Yingying; Qu, Yao; Tian, Hongkun; Zhang, Jingping; Xie, Zhiyuan; Geng, Yanhou; Wang, Fosong [Chemistry - An Asian Journal, 2010, vol. 5, # 4, p. 932 - 940]

30
[ 540-80-7 ]
[ 117-79-3 ]
[ 572-83-8 ]

Yield	Reaction Conditions	Operation in experiment
89%	With hydrogenchloride; copper(ll) bromide; In water; acetonitrile;	1-1) Synthesis of 2-bromoanthraquinone 200 g (0.896 mol) of <strong>[117-79-3]2-aminoanthraquinone</strong>, 240.13 g (1.075 mol) of CuBr2, 4L of acetonitrile, and 138.58 g (1.344 mol) of t-butylnitrite were loaded into a 10 L reactor and then the temperature was increased to 65 C. After 3-hour reaction, the temperature was decreased to room temperature and then 3 L of 2N HCl was added thereto, thereby producing a solid. The solid was filtered and washed with 10 L of water, thereby producing a dark brown solid (203 g, 89%).

Reference： [1]Patent: US2011/31484,2011,A1

31
HCl(aq) [ No CAS ]
[ 90-11-9 ]
[ 572-83-8 ]
NaH₂PO_2.H₂O [ No CAS ]
[ 474688-76-1 ]

Yield	Reaction Conditions	Operation in experiment
64%	With Ki; In tetrahydrofuran; n-butyllithium; toluene;	3-1) Synthesis of 2-bromo-9,10-di(naphthyl)anthracene 360 g (1.74 mol) of bromonaphthalene was dissolved with THF in a 5 L flask and the temperature was lowered to -78 C. and 1600 ml (1.6 mol) of 1.6M n-BuLi was slowly added dropwise thereto. The mixture was stirred for one hour, and then 200 g (0.68 mol) of 2-bromoanthraquinone was added thereto in a solid state and then the temperature was slowly raised to room temperature and the resultant mixture was stirred. After 12 hours, 500 ml of 2N HCl(aq) was added thereto. Then, an organic layer was isolated and dried over MgSO4 and condensed under reduced pressure, thereby producing Compound C. The Compound C was used in the subsequent reaction without purification. Compound C, 346 g (2.09 mol) of KI, and 443 g (4.1 mol) of NaH2PO2.H2O were diluted with an acetic acid and then the mixture was refluxed while heating. The temperature was lowered to room temperature and thus a solid was precipitated. The solid was filtered, washed with excess water and MeOH, and re-crystallized with 300 ml of toluene, thereby producing 2-bromo-9,10-di(2-naphthyl)anthracene (230 g, 64%).

Reference： [1]Patent: US2011/31484,2011,A1

32
[ 108-86-1 ]
[ 572-83-8 ]
[ 860530-98-9 ]

Yield	Reaction Conditions	Operation in experiment
60%	Stage #1: bromobenzene With n-butyllithium In tetrahydrofuran at -78℃; for 1h; Inert atmosphere; Stage #2: 2-bromoanthracene-9,10-dione In tetrahydrofuran at -78 - 20℃; Inert atmosphere;	1 synthesis of intermediate 1 3 opening 500 ml multi function cap to bromobenzene (16.4g, 0.11mol) THF and he and agitating the added under nitrogen. Reaction temperature and in -78 ° C n-BuLi (65.3 ml, 0.11mol) is slowly added to the polymerization reaction mixture to visitor is checked through a stirring time 1. 2-bromoanthracene-9 herein, 10-dione (10g, 0.04mol) adding an 4-5 time was reacted at ambient. After reaction is completed, water are added after vacuum distilling a reaction mixture, out by extracting with distilled water and a Methylene Chloride. Extracted Methylene Chloride layer MgSO4after for holding a order to form an exterior, of methanol removing the solvent by the string grudge liquid obtained. An Column Chromatography method using yellow solid(1) separated the. (9.2g, 60%)
60%	Stage #1: bromobenzene With n-butyllithium In tetrahydrofuran at -78℃; for 1h; Inert atmosphere; Stage #2: 2-bromoanthracene-9,10-dione In tetrahydrofuran at 20℃;	1 Synthesis of intermediate (1) Three-necked 500ml flask was added bromobenzene (16.4g, 0.11mol) and THF under nitrogen and the mixture was stirred. And added slowly to the reaction temperature at -78 n-BuLi (65.3mL, 0.11mol) and stirred 1 hour.To this was added the 2-bromoanthracene-9,10-dione (10g, 0.04mol) and allowed to react at room temperature for 4 to 5 hours.After completion of the reaction, after addition of water, and distilled under reduced pressure, the reaction solution was extracted with Methylene Chloride with distilled water. After japahjun moisture Methylene Chloride the extracted layer with MgSO4, the solvent was removed by distillation under reduced pressure to give a viscous liquid. The liquid using a method Column Chromatography was isolated yellow solid (1). (9.2g, 60%)
	Stage #1: bromobenzene With n-butyllithium In tetrahydrofuran; hexane at -78℃; for 2h; Inert atmosphere; Stage #2: 2-bromoanthracene-9,10-dione In tetrahydrofuran; hexane at -78 - 25℃; Inert atmosphere; Stage #3: With ammonium chloride In tetrahydrofuran; hexane; water	1 Preparation of Compound (112)Under nitrogen atmosphere, 1-bromobenzene (7.1 g, 45.0 mmol) was dissolved in tetrahydrofuran (100 mL), and n-BuLi (2.5 M in n-hexane) (27.0 mL, 67.5 mmol) was added dropwise at -78° C. thereto. After stirring for 2 hours, the reaction mixture was slowly added dropwise at -78° C. to a solution of 2-bromoanthraquinone (Compound III) (4.3 g, 15.0 mmol) dissolved in tetrahydrofuran (50 mL) at 25° C. under nitrogen atmosphere. The temperature was slowly raised from -78° C. to 25° C., and the reaction mixture was stirred for 12 hours. After quenching the reaction by adding saturated aqueous ammonium chloride solution (50 mL), the reaction mixture was extracted with ethyl acetate (100 mL), dried over anhydrous magnesium sulfate. Removal of the organic layer under reduced pressure and recrystallization from dichloromethane (100 mL) gave Compound (112) (5.7 g, 12.9 mmol).

	Stage #1: bromobenzene With n-butyllithium In tetrahydrofuran at -78℃; for 1h; Stage #2: 2-bromoanthracene-9,10-dione In tetrahydrofuran at 20℃; for 6h; Stage #3: With hydrogenchloride In tetrahydrofuran; water	1.1-2 1-2) Synthesis of 2-bromo-9,10-diphenylanthracene 164 g (1.045 mol) of bromobenzene was loaded into a 2 L reactor, and then 700 ml of THF was added thereto. The temperature of the reactor was lowered to - 78°C, and then 653.06 ml (1.045 mol) of 1.6M n-BuLi was slowly added dropwise thereto. Then, the mixture was stirred for about one hour at low temperature and then, 100 g (0.348 mol) of 2-bromoanthraquinone obtained from 1-1) was added thereto. The resultant mixture was reacted at room temperature for 6 hours and then 200 ml of 2N HCl was added thereto. The reaction mixture was subjected to layer isolation and an organic solvent included in an organic layer was removed under reduced pressure, thereby obtaining intermediate A. Intermediate A, 173.45 g (1.045 mol) of KI, 221.50 g (2.090 mol) of sodium hyphophousfite, and 1000 ml of AcOH were added to a 2 L reactor and refluxed for 3 hours. The resultant product was cooled to room temperature, thereby producing a solid. The solid was filtered and washed with methanol and water, and then, re-crystallized with toluene, thereby producing a brown solid (105 g, 73%).
	Stage #1: bromobenzene With n-butyllithium In tetrahydrofuran at -78℃; for 1.5h; Stage #2: 2-bromoanthracene-9,10-dione In tetrahydrofuran at 20℃; for 24h; Stage #3: With hydrogenchloride In tetrahydrofuran; water	4.4-1 Synthesis Example 4-(1): Synthesis of 2-bromo-9,10-diphenylanthracene While stirring the 2L round bottom flask, 164.1 g (1.045 mol) and 700 ml (THF) of bromobenzene were added.After the temperature was dropped to -78 ° C, 227.5 ml (1.045 mol) of n-BuLi was slowly added dropwise. After the dropwise addition, stir for 1 hour and 30 minutes,100 g (0.348 mol) of 2-bromoanthraquinone was dissolved in 300 ml of THF and rapidly added.After standing for 10 minutes, the mixture was stirred at room temperature for 1 day.When the reaction was completed, 200 ml of 2N hydrochloric acid was added to make it acidic, and concentrated. The concentrated reactant was placed in a 2 L round bottom flask, KI 173.45 g (1.045 mol), NaH2PO2H2O 221.50 g (2.090 mol),It was refluxed with 1000 ml of acetic acid for 3 hours. When the reaction is finished, it is lowered to room temperature,The resulting solid is filtered and washed with methanol,Recrystallized from toluene. As a result, 40.0 g (0.097 mol, yield 27.94%) of an ocher solid was obtained.

Reference： [1]Current Patent Assignee: WS CO., LTD. - KR101528769, 2015, B1 Location in patent: Paragraph 0088; 0089; 0090; 0091; 0092
[2]Current Patent Assignee: WS CO., LTD. - KR101528767, 2015, B1 Location in patent: Paragraph 0088-0092
[3]Current Patent Assignee: DOW INC - US2011/54228, 2011, A1 Location in patent: Page/Page column 6
[4]Current Patent Assignee: SAMSUNG ELECTRONICS CO.,LTD.; Samsung Display (in: Samsung) - EP2292604, 2011, A2 Location in patent: Page/Page column 22
[5]Current Patent Assignee: HODOGAYA CHEMICAL CO LTD - KR101553561, 2015, B1 Location in patent: Paragraph 0185-0189

33
[ 92-66-0 ]
[ 572-83-8 ]
[ 1158227-80-5 ]

Yield	Reaction Conditions	Operation in experiment
	Stage #1: 4-bromo-1,1'-biphenyl With n-butyllithium In tetrahydrofuran; hexane at -78℃; for 2h; Inert atmosphere; Stage #2: 2-bromoanthracene-9,10-dione In tetrahydrofuran; hexane at -78 - 25℃; Inert atmosphere; Stage #3: With ammonium chloride In tetrahydrofuran; hexane; water	6 Preparation of Compound (133)Under nitrogen atmosphere, 4-bromobiphenyl (21 g, 90 mmol) was dissolved in tetrahydrofuran (200 mL), and n-BuLi (2.5 M in n-hexane) (54 mL, 135 mmol) was slowly added dropwise thereto at -78° C. After stirring for 2 hours, the reaction mixture was slowly added dropwise at -78° C. to a solution of 2-bromoanthraquinone (Compound III) (8.7 g, 30 mmol) dissolved in tetrahydrofuran (100 mL) at 25° C. under nitrogen atmosphere. The temperature was slowly raised from -78° C. to 25° C., and the reaction mixture was stirred for 12 hours. After quenching the reaction by adding saturated aqueous ammonium chloride solution (300 mL), the reaction mixture was extracted with ethyl acetate (300 mL), dried over anhydrous magnesium sulfate. Evaporation of the organic layer under reduced pressure and recrystallization from dichloromethane (200 mL) gave Compound (133) (14.8 g, 24.9 mmol).
	Stage #1: 4-bromo-1,1'-biphenyl With n-butyllithium In tetrahydrofuran at -78℃; for 1.5h; Stage #2: 2-bromoanthracene-9,10-dione In tetrahydrofuran at 20℃; for 24h; Stage #3: With hydrogenchloride In tetrahydrofuran; water	6.6-1 Synthesis Example 6- (1): 2-Bromo-9,10-di (4'-biphenyl) anthracenesynthesis 73.1 g of 4-bromobiphenyl with stirring 500 ml round bottom flask(0.313 mol) and 200 ml of THF were added.After the temperature was dropped to -78 ° C, 20.5 ml (0.313 mol) of n-BuLi was slowly added dropwise.After the dropwise addition, the mixture was stirred for 1 hour and 30 minutes, and 30.0 g (0.104 mol) of 2-bromoanthraquinone was dissolved in 100 ml of THF and rapidly added.After standing for 10 minutes, the mixture was stirred at room temperature for 1 day. When the reaction ends,150 ml of 2N hydrochloric acid was added to make it acidic, and concentrated.The concentrated reaction was placed in a 500 ml round-bottom flask, KI 52.04 g (0.313 mol), NaH2PO2H2O 66.45 g (0.627 mol),It was refluxed with 300 ml of acetic acid for 3 hours.Upon completion of the reaction, it was lowered to room temperature,The resulting solid was filtered, washed with methanol, and recrystallized from toluene.As a result, 40.0 g (0.071 mol, yield 68.2%) of an ocher solid was obtained.

Reference： [1]Current Patent Assignee: DOW INC - US2011/54228, 2011, A1 Location in patent: Page/Page column 13
[2]Current Patent Assignee: HODOGAYA CHEMICAL CO LTD - KR101553561, 2015, B1 Location in patent: Paragraph 0212-0217

34
[ 572-83-8 ]
[ 28320-31-2 ]
[ 955123-67-8 ]

Yield	Reaction Conditions	Operation in experiment
	Stage #1: 2-bromo-9,9-dimethyl-9H-fluorene With n-butyllithium In tetrahydrofuran; hexane at -78℃; for 2h; Inert atmosphere; Stage #2: 2-bromoanthracene-9,10-dione In tetrahydrofuran; hexane at -78 - 25℃; Inert atmosphere; Stage #3: With ammonium chloride In tetrahydrofuran; hexane; water	7 Preparation of Compound (138)Under nitrogen atmosphere, Compound (137) (14.3 g, 52.2 mmol) was dissolved in tetrahydrofuran (150 mL), and n-BuLi (2.5 M in n-hexane) (31.3 mL, 78.3 mmol) was slowly added dropwise at -78° C. thereto. After stirring for 2 hours, the reaction mixture was slowly added dropwise at -78° C. to a solution of 2-bromoanthraquinone (Compound III) (5.0 g, 17.4 mmol) dissolved in tetrahydrofuran (50 mL) at 25° C. under nitrogen atmosphere. The temperature was slowly raised from -78° C. to 25° C., and the reaction mixture was stirred for 12 hours. After quenching the reaction by adding saturated aqueous ammonium chloride solution (200 mL), the reaction mixture was extracted with ethyl acetate (200 mL), and the extract was dried over anhydrous magnesium sulfate and filtered. Evaporation of the organic layer under reduced pressure and recrystallization from hexane (200 mL) gave Compound (138) (9.9 g, 14.6 mmol).

Reference： [1]Current Patent Assignee: DOW INC - US2011/54228, 2011, A1 Location in patent: Page/Page column 15

35
[ 572-83-8 ]
[ 677-22-5 ]
[ 1269013-86-6 ]

Yield	Reaction Conditions	Operation in experiment
65%	Stage #1: 2-bromoanthracene-9,10-dione; tert-butylmagnesium chloride In tetrahydrofuran; diethyl ether at -78 - 20℃; for 1.5h; Inert atmosphere; Stage #2: With ammonium chloride In tetrahydrofuran; diethyl ether; water	1 Synthesis of Intermediate 3; 2.9 g (10 mmol) of 2-bromo-anthraquinone was dissolved in 50 mL of purified tetrahydrofuran under a nitrogen atmosphere. The reaction product was cooled to -78°C and then 5 mL of (CH3)3CMgCl (2.0M in diethylether) was slowly added thereto. The reaction product was stirred at -78°C for 30 minutes and the temperature thereof was increased to room temperature by removing a cooler. The reaction product was stirred for one hour and was heated to 0°C when the reaction was completed, and then 10 mL of an ammonium chloride aqueous solution was slowly added thereto. The reaction product was extracted twice with 40 mL of diethylether. The organic layer was collected and dried using magnesium sulfate, followed by filtration. The solvent was evaporated, and the residue was separated and purified using silica gel column chromatography to obtain 2.6 g (yield: 65 %) of Intermediate 3. This compound was identified using HR-MS. C22H27BrO2 calc.: 402.1194; found 402.1198.

Reference： [1]Current Patent Assignee: SAMSUNG ELECTRONICS CO.,LTD.; Samsung Display (in: Samsung) - EP2292602, 2011, A1 Location in patent: Page/Page column 26-27

36
[ 1059575-28-8 ]
[ 572-83-8 ]
[ 1337570-09-8 ]

Yield	Reaction Conditions	Operation in experiment
100%	Stage #1: 2,5-dimethyl-4-trimethylsilyl-1-phenylboronic acid; 2-bromoanthracene-9,10-dione With sodium carbonate In ethanol; water; toluene for 0.25h; Inert atmosphere; Stage #2: With tetrakis(triphenylphosphine) palladium⁽⁰⁾ In ethanol; water; toluene for 36h; Reflux; Inert atmosphere;
98%	With tetrakis(triphenylphosphine) palladium⁽⁰⁾; sodium carbonate In tetrahydrofuran; water Reflux;
96%	With tetrakis(triphenylphosphine) palladium⁽⁰⁾; sodium carbonate In ethanol; water; toluene Reflux; Inert atmosphere;

76%	With tetrakis(triphenylphosphine) palladium⁽⁰⁾; sodium carbonate In tetrahydrofuran; water at 85℃; for 20h; Inert atmosphere;
	With tetrakis(triphenylphosphine) palladium⁽⁰⁾; sodium carbonate In water; toluene

Reference： [1]Bonn, Annabell G.; Neuburger, Markus; Wenger, Oliver S. [Inorganic Chemistry, 2014, vol. 53, # 20, p. 11075 - 11085]
[2]Kuss-Petermann, Martin; Wenger, Oliver S. [Angewandte Chemie - International Edition, 2016, vol. 55, # 2, p. 815 - 819][Angew. Chem., 2016, vol. 128, # 2, p. 826 - 830,5]
[3]Hankache, Jihane; Wenger, Oliver S. [Chemical Communications, 2011, vol. 47, # 36, p. 10145 - 10147]
[4]Neumann, Svenja; Wenger, Oliver S. [Inorganic Chemistry, 2019, vol. 58, # 1, p. 855 - 860]
[5]Location in patent: scheme or table Hankache, Jihane; Wenger, Oliver S. [Physical Chemistry Chemical Physics, 2012, vol. 14, # 8, p. 2685 - 2692]

37
[ 572-83-8 ]
[ 73183-34-3 ]
[ 1337570-04-3 ]

Yield	Reaction Conditions	Operation in experiment
97%	With (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; potassium acetate In dimethyl sulfoxide at 80℃; for 24h; Inert atmosphere;
89.6%	With (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; potassium carbonate In toluene Inert atmosphere; Reflux;	1 Synthetic Example 1 Synthesis of Compound A1 Under nitrogen protection, 2-bromoanthraquinone M1 (26.5 g, 0.01 mol), pinacol boronate (0.015 mol), Pd(dppf)Cl2(1%) Potassium carbonate was mixed in 500 ml of toluene, heated to reflux, and reacted overnight. The reaction liquid was subjected to column chromatography, concentrated, and washed with petroleum ether to give Intermediate M2 (20.1 g, yield 89.6%).
89.6%	With (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; potassium carbonate In toluene Inert atmosphere; Reflux;	1 Under nitrogen protection,2-bromoanthraquinone (M1) (26.5 g, 0.01 mol),Bis(pinacolato)diboron (0.015mol),Pd(dppf)Cl2(1%),Potassium carbonate is dissolved in 500ml of toluene.Heat to reflux and react overnight.Reactant column chromatography, concentration, petroleum ether wash,Intermediate M2 was obtained (20.1 g, yield 89.6%).

75%	With (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; potassium acetate In 1,4-dioxane at 110℃; for 24h; Schlenk technique;
48%	With dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH₂Cl₂; potassium acetate In dimethyl sulfoxide at 80℃; for 48h;
	With (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride
	With palladium bis[bis(diphenylphosphino)ferrocene] dichloride; potassium acetate In dimethyl sulfoxide at 80℃; for 48h; Inert atmosphere; Schlenk technique;

Reference： [1]Kawai, Takuma; Oyaizu, Kenichi; Nishide, Hiroyuki [Macromolecules, 2015, vol. 48, # 8, p. 2429 - 2434]
[2]Current Patent Assignee: BEIJING ETERNAL MATERIAL TECHNOLOGY CO LTD - CN107915732, 2018, A Location in patent: Paragraph 0069; 0070; 0073; 0087; 0090
[3]Current Patent Assignee: BEIJING ETERNAL MATERIAL TECHNOLOGY CO LTD - CN107954942, 2018, A Location in patent: Paragraph 0069; 0074; 0090; 0096
[4]Liu, Shunjie; Zhang, Haoke; Li, Yuanyuan; Liu, Junkai; Du, Lili; Chen, Ming; Kwok, Ryan T. K.; Lam, Jacky W. Y.; Phillips, David Lee; Tang, Ben Zhong [Angewandte Chemie - International Edition, 2018, vol. 57, # 46, p. 15189 - 15193][Angew. Chem., 2018, vol. 130, p. 15409 - 15413,5]
[5]Hankache, Jihane; Wenger, Oliver S. [Chemical Communications, 2011, vol. 47, # 36, p. 10145 - 10147]
[6]Li, Yanxia; Tan, Tingfeng; Wang, Shirong; Xiao, Yin; Li, Xianggao [Dyes and Pigments, 2017, vol. 144, p. 262 - 270]
[7]Kakiuchi, Fumitoshi; Kochi, Takuya; Kumagai, Takaaki; Muto, Kazuma [Angewandte Chemie - International Edition, 2021, vol. 60, # 46, p. 24500 - 24504][Angew. Chem., 2021, vol. 133, # 46, p. 24705 - 24709]

38
[ 572-83-8 ]
[ 591-51-5 ]
[ 1299493-18-7 ]

Yield	Reaction Conditions	Operation in experiment
	Stage #1: 2-bromoanthracene-9,10-dione; phenyllithium In diethyl ether; dibutyl ether; toluene at -20℃; for 6h; Stage #2: With water In diethyl ether; dibutyl ether; toluene	1 Exemplary Synthesis 1; Synthesis of Compound 1; Synthesis of 9,10-Diphenylanthracene-2-Boronic Acid; An amount of 6.8 g (23.7 mmol) of 2-bromoanthraquinone was suspended in a mixed solvent of 50 ml of dehydrated toluene and 50 ml of dehydrated ether and cooled to -20° C. An amount of 26.3 ml (50 mmol) of a solution of phenyllithium (1.9 mmol/ml) in butylether was added and allowed to react for six hours. Then, distilled water was added to stop the reaction. Then, the separated organic layer was applied to column chromatography to obtain a diol form. Then, the obtained diol form, 39 g (237 mmol) of potassium iodide, and 41 g (390 mmol) of sodium hypophosphite monohydrate were dissolved in acetic acid and refluxed for six hours. After cooling, the deposit was filtered and purified by column chromatography to obtain 4.68 g (11.4 mmol) of 2-bromo-9,10-diphenylanthracene. The yield was 48.3%.An amount of 4.68 g (11.4 mmol) of 2-bromo-9,10-diphenylanthracene was dissolved in dehydrated THF and cooled to -80° C. An amount of 7.9 ml (12 mmol) of a solution of n butyllithium in n hexane was added dropwise and, 40 minutes later, 3.33 g (22.8 mmol) of triethyl borate was further added. After two-hour reaction, a dilute hydrochloric acid solution was added and the mixture was allowed to stand for 12 hours. Then, the separated organic layer was recrystallized to obtain 3.07 g (8.2 mmol) of 9,10-diphenylanthracene-2-boronic acid. The yield was 72%.

Reference： [1]Current Patent Assignee: FUTABA CORPORATION - US2011/295017, 2011, A1 Location in patent: Page/Page column 21

39
[ 572-83-8 ]
benzofurano[3,2-b]dibenzofuran-6-boronic acid [ No CAS ]
[ 1256544-91-8 ]

Yield	Reaction Conditions	Operation in experiment
65%	With sodium carbonate In 1,2-dimethoxyethane; water for 8h; Inert atmosphere; Reflux;	49.49-1 (49-1) Synthesis of 2-[benzofurano[3,2-b]dibenzofuran-6-yl]-9,10-anthraquinone In the atmosphere of argon, 28.5g of 2-bromoantraquinone, 30.2g of benzofurano[3,2-b]dibenzofuran-6-boronic acid, 2.31g of tetrakistriphenylphosphine palladium (0), 400 mL of 1,2-dimethoxyethane and 200 mL of a 2M aqueous sodium carbonate solution were placed in a flask. The resulting mixture was stirred with heating under reflux for 8 hours. The resulting mixture was cooled to room temperature, and deposited solids were filtered out. The resulting solids were washed with water and methanol, and recrystallized from toluene, whereby 30.2g (yield: 65%) of2-[benzofurano[3,2-b]dibenzofuran-6-yl]-9,10-anthraquinone was obtained

Reference： [1]Current Patent Assignee: IDEMITSU KOSAN CO LTD - EP2436679, 2012, A1 Location in patent: Page/Page column 74

40
[ 572-83-8 ]
[ 89343-06-6 ]
[ 1403609-28-8 ]

Yield	Reaction Conditions	Operation in experiment
80%	Stage #1: tris-iso-propylsilyl acetylene With n-butyllithium In tetrahydrofuran; hexane at -78℃; Inert atmosphere; Stage #2: 2-bromoanthracene-9,10-dione In tetrahydrofuran; hexane at -78 - 20℃; for 22.5h; Inert atmosphere; Stage #3: With acetic acid; tin(ll) chloride In tetrahydrofuran; water at 20℃;
80%	Stage #1: tris-iso-propylsilyl acetylene With n-butyllithium In tetrahydrofuran; hexane at -78℃; for 2h; Inert atmosphere; Stage #2: 2-bromoanthracene-9,10-dione In tetrahydrofuran; hexane at -78 - 25℃; for 22.5h; Inert atmosphere; Stage #3: With acetic acid; tin(ll) chloride In tetrahydrofuran; water at 20℃; for 12h; Inert atmosphere;	2 The method for preparing 2-bromo-9,10-ditriisopropylsilylethynylanthracene 1 includes the following steps: Under nitrogen protection, add 1.5 mL of anhydrous tetrahydrofuran and triisopropylsilylacetylene (0.52 mL, 2.31 mmol) to a three-necked flask equipped with a stirrer, cool to -78 ° C, and add 3.14 mmol (1.90 mL) ) Butyl lithium (a hexane solution with a concentration of 1.65 M of butyl lithium), and stirred for 2 hours to obtain a solution A. 2-bromoanthraquinone (2.30 g, 8.03 mmol) was dissolved in anhydrous tetrahydrofuran (15 ml) and added to the solution A, followed by stirring at -78 ° C for 1.5 hours, and then warming to room temperature of 20-25 ° C. The reaction was performed at room temperature for 21 hours, and then quenched with water. The resulting intermediate was extracted with chloroform, the organic layer was washed with water, dried over anhydrous sodium sulfate, and concentrated in vacuo.The concentrated intermediate product was dissolved in 35 mL of tetrahydrofuran and a mixed solution of stannous chloride (4.54 g, 24 mmol) dissolved in water (20 mL) and glacial acetic acid (3.60 mL, 62.9 mmol) was added dropwise (i.e., A mixed solution of stannous chloride in water and glacial acetic acid), and stirred at room temperature for 12 hours. After pouring into water, the solid obtained by filtration was washed with ethyl acetate. The filtrate was transferred to a separating funnel, and the organic layer was separated. The aqueous layer was extracted with ethyl acetate. The combined organic layers were washed with water, dried over anhydrous sodium sulfate, and concentrated in vacuo. Purification by silica gel column chromatography (petroleum ether as eluent) gave 2-bromo-9,10-ditriisopropylsilylethynylanthracene 1 (3.98 g, 6.45 mmol) as a green solid in a yield of 80%.Send feedbackHistorySavedCommunity
80%	Stage #1: tris-iso-propylsilyl acetylene With n-butyllithium In tetrahydrofuran; hexane at -78℃; for 2h; Inert atmosphere; Stage #2: 2-bromoanthracene-9,10-dione In tetrahydrofuran; hexane at -78 - 25℃; for 22.5h; Inert atmosphere; Stage #3: With acetic acid; tin(ll) chloride In tetrahydrofuran; water at 20 - 25℃; for 12h;	2 Under nitrogen protection, add 1.5 mL of anhydrous tetrahydrofuran and triisopropylsilylacetylene (0.52 mL, 2.31 mmol) to a three-necked flask equipped with a stirrer, cool to -78 ° C, and add 3.14 mmol (1.96 mL) ) N-butyllithium (1.6M hexane solution with n-butyllithium concentration), and stirred for 2 hours to obtain solution A. 8.03 mmol of 2-bromoanthraquinone (2.30 g) was dissolved in 15 ml of anhydrous tetrahydrofuran and added to the solution A, followed by stirring at -78 ° C for 1.5 hours, and then warming to room temperature of 20-25 ° C. The reaction was performed at room temperature for 21 hours, and then quenched with water. The resulting intermediate was extracted with chloroform, the organic layer was washed with water, dried over anhydrous sodium sulfate, and concentrated in vacuo. The concentrated intermediate product was dissolved in 35 mL of tetrahydrofuran and a mixed solution of stannous chloride (4.54 g, 24 mmol) dissolved in water (20 mL) and glacial acetic acid (3.60 mL, 62.9 mmol) was added dropwise (i.e., A mixed solution of stannous chloride in water and glacial acetic acid), and stirred at room temperature for 12 hours. After pouring into water, the solid obtained by filtration was washed with ethyl acetate. The filtrate was transferred to a separating funnel, and the organic layer was separated. The aqueous layer was extracted with ethyl acetate. The combined organic layers were washed with water, dried over anhydrous sodium sulfate, and concentrated in vacuo. Purification by silica gel column chromatography (petroleum ether as eluent) gave 2-bromo-9,10-ditriisopropylsilylethynylanthracene 1 (3.98 g, 6.45 mmol) as a green solid in a yield of 80%.

Reference： [1]Goto, Kiyohiko; Yamaguchi, Ryuichi; Hiroto, Satoru; Ueno, Hiroshi; Kawai, Tsuyoshi; Shinokubo, Hiroshi [Angewandte Chemie - International Edition, 2012, vol. 51, # 41, p. 10333 - 10336]
[2]Current Patent Assignee: TIANJIN UNIVERSITY - CN110627602, 2019, A Location in patent: Paragraph 0074; 0083; 0085-0090
[3]Current Patent Assignee: TIANJIN UNIVERSITY - CN110627601, 2019, A Location in patent: Paragraph 0072; 0082-0089

41
[ 572-83-8 ]
[ 1415568-88-5 ]
[ 1415568-95-4 ]

Yield	Reaction Conditions	Operation in experiment
37%	With copper(l) iodide; tetrakis(triphenylphosphine) palladium⁽⁰⁾; triethylamine In N,N-dimethyl-formamide at 80℃; for 16h; Inert atmosphere;	5-(9,10-Dioxo-9,10-dihydroanthracen-2-yl)-3,3-bis((9,10-dioxo-9,10-dihydroanthracen-2-yl)ethynyl)pent-4-yn-1-yl pivalate (9) TEM unit 1 (10 mg, 0.046 mmol), 2-bromoanthraquinone (43 mg, 0.15 mmol), CuI (1.8 mg, 9.2 mmol), and Pd(PPh3)4 (5.3 mg, 4.6 mmol) were placed in a dried two-neck round bottom flask, under an argon atmosphere. Anhydrous N,N-dimethylformamide (1.0 ml) and triethylamine (1.0 ml) were added and the reaction mixture was stirred at 80 °C for 16 h. The reaction mixture was concentrated in vacuo. The residue was purified by column chromatography on silica gel (CHCl3) and then by GPC to give 9 (14 mg, 37%). 1H NMR (600 MHz, CDCl3) δ 1.22 (s, 9H), 2.73 (t, J = 7.2 Hz, 2H), 4.62 (t, J = 7.2 Hz, 2H), 7.81-7.84 (m, 6H), 7.95 (dd, J = 1.8 Hz, 3H), 8.31-8.34 (m, 9H), 8.42 (d, J = 1.8 Hz, 3H); 13C NMR (150 MHz, CDCl3) δ 27.173, 28.466, 38.758, 41.822, 60.917, 81.079, 89.658, 127.335, 127.354, 127.382, 128.024, 130.781, 132.897, 133.309, 133.357, 133.434, 134.295, 134.362, 136.995, 178.445, 182.361, 182.437; HRMS Calculated for [C56H34NaO8]+: 857.2146, found: 857.2147.

Reference： [1]Otabe, Takahiro; Matsumoto, Saki; Nakagawa, Hiroki; Hong, Changfeng; Dohno, Chikara; Nakatani, Kazuhiko [Tetrahedron Letters, 2013, vol. 54, # 2, p. 143 - 146]

42
[ 572-83-8 ]
[ 81290-20-2 ]
[ 1449478-73-2 ]

Yield	Reaction Conditions	Operation in experiment
100%	Stage #1: 2-bromoanthracene-9,10-dione; (trifluoromethyl)trimethylsilane With potassium carbonate In N,N-dimethyl-formamide at 20℃; for 15h; Stage #2: With hydrogenchloride In ethanol; water for 3h; Reflux;

Reference： [1]Yamada, Shigeyuki; Kinoshita, Keita; Iwama, Shota; Yamazaki, Takashi; Kubota, Toshio; Yajima, Tomoko [RSC Advances, 2013, vol. 3, # 19, p. 6803 - 6806]

43
[ 2554-06-5 ]
[ 572-83-8 ]
[ 13388-33-5 ]

Yield	Reaction Conditions	Operation in experiment
96%	With tetrabutyl ammonium fluoride; bis(dibenzylideneacetone)-palladium(0); johnphos; In tetrahydrofuran; at 80℃; for 8h;Inert atmosphere;	2-Bromoanthraquinone (1.5 g, 5.22 mmol), bis(dibenzylideneacetone)palladium(0) (0.060 g, 0.104 mmol), biphenyl-2-yldi-tert-butylphosphine (0.062 g, 0.209 mmol) are dissolved in a 0.3 M solution of tetrabutylammonium fluoride in tetrahydrofuran. The solution is purged with argon, and <strong>[2554-06-5]2,4,6,8-tetramethyl-2,4,6,8-tetravinyl-1,3,5,7,2,4,6,8-tetraoxatetrasiloxane</strong> (0.902 nil, 2.61 mmol) is added dropwise. The mixture is stirred at 80° C. under an argon atmosphere for 8 hours. The reaction mixture is cooled to room temperature and added to 250 ml of ethanol. The precipitate is filtered off and washed twice with n-hexane. After drying under reduced pressure, almost pure 2-vinylanthraquinone (3) (1.175 g, 5.02 mmol, 96percent) is obtained as a yellowish solid, the purity of which is sufficient for the next reaction step. Anal. Calcd for C16H10O2: C, 81.90; H, 4.30. Found: C, 81.85; H, 4.31. 1H NMR (CDCl3, 300 MHz, ppm): delta 5.54 (d, 1H), 6.05 (d, 1H), 6.87 (dd, 1H), 7.80 (m, 3H), 8.32 (m, 4H). 13C NMR (CDCl3, 75 MHz, ppm): delta 183.2, 182.6, 143.2, 135.4, 134.1, 134.0, 133.8, 133.6, 133.5, 132.5, 131.4, 128.3, 127.8, 127.2, 124.8, 118.4.

Reference： [1]Journal of Materials Chemistry A,2014,vol. 2,p. 8999 - 9001
[2]Patent: US9890230,2018,B2 .Location in patent: Page/Page column 42; 43

44
[ 110-91-8 ]
[ 201230-82-2 ]
[ 572-83-8 ]
2-(morpholine-4-carbonyl)anthracene-9,10-dione [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
96%	With C₅₁H₄₅NO₄P₂PdS; triethylamine In 1,4-dioxane at 45℃; for 16h; Sealed tube; Inert atmosphere;

Reference： [1]Friis, Stig D.; Skrydstrup, Troels; Buchwald, Stephen L. [Organic Letters, 2014, vol. 16, # 16, p. 4296 - 4299]

45
[ 201230-82-2 ]
[ 572-83-8 ]
[ 2235-46-3 ]
3-(9,10-dioxo-9,10-dihydroanthracen-2-yl)-N,N-diethyl-3-oxopropanamide [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
91%	Stage #1: carbon monoxide; 2-bromoanthracene-9,10-dione; N,N-diethyl-3-oxobutanamide With dichloro(1,5-cyclooctadiene)palladium(II); triethylamine; 4,5-bis(diphenylphosphino)-9,9-dimethylxanthene; magnesium chloride In 1,4-dioxane at 80℃; for 18h; Stage #2: With hydrogenchloride In 1,4-dioxane; water at 80℃; for 1h;
91%	With dichloro(1,5-cyclooctadiene)palladium(II); triethylamine; 4,5-bis(diphenylphosphino)-9,9-dimethylxanthene; magnesium chloride In 1,4-dioxane at 80℃; for 18h; Sealed tube;

Reference： [1]Nielsen, Dennis U.; Korsager, Signe; Lindhardt, Anders T.; Skrydstrup, Troels [IUBMB Life, 2014, vol. 356, # 17, p. 3519 - 3524]
[2]Nielsen, Dennis U.; Korsager, Signe; Lindhardt, Anders T.; Skrydstrup, Troels [Advanced Synthesis and Catalysis, 2014, vol. 356, # 17, p. 3519 - 3524]

46
[ 572-83-8 ]
[ 201802-67-7 ]
2-(4-(diphenylamino)phenyl)anthracene-9,10-dione [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
84.26%	Stage #1: 2-bromoanthracene-9,10-dione; 4-(diphenylamino)phenyl boronic acid With teterabutylammonium; potassium carbonate In toluene at 20℃; for 0.25h; Inert atmosphere; Stage #2: With tetrakis(triphenylphosphine) palladium⁽⁰⁾ In toluene for 12h; Reflux; Inert atmosphere;	1 2.3.1 Synthesis of 4,4'-((4-(9,10-dioxo-9,10-dihydroanthracen-2-yl)phenyl)azanediyl)dibenzaldehyde (dye 1) General procedure: Compound 7 (0.38 g, 1.0 mmol), 10 (0.44 g, 1.3 mmol), tetrabutylammonium (0.16 g, 0.5 mmol) were dissolved in toluene (40 mL) under argon, and K2CO3 (2 M, 2.5 mL) was added. The mixture was stirred at room temperature for 15 min, and then Pd(PPh3)4 catalyst (0.05 g, 0.04 mmol) was added. The reaction mixture was heated to reflux for 12 h. After cooling, the product was extracted with CH2Cl2, washed with water, dried over anhydrous MgSO4. The organic layer was evaporated and the compound was purified by flash chromatography on silica gel column (petroleum ether:ethyl acetate = 10:1 as eluent) to give orange solid 0.28 g, yield: 54.90%, m.p. 182-183 °C.
61%	With bis-triphenylphosphine-palladium(II) chloride; potassium phosphate In N,N-dimethyl-formamide at 20 - 80℃; for 15h; Inert atmosphere;

Reference： [1]Li, Yanxia; Tan, Tingfeng; Wang, Shirong; Xiao, Yin; Li, Xianggao [Dyes and Pigments, 2017, vol. 144, p. 262 - 270]
[2]Zhang, Qisheng; Kuwabara, Hirokazu; Potscavage, William J.; Huang, Shuping; Hatae, Yasuhiro; Shibata, Takumi; Adachi, Chihaya [Journal of the American Chemical Society, 2014, vol. 136, # 52, p. 18070 - 18081]

47
[ 572-83-8 ]
[ 100622-34-2 ]
C₂₈H₁₆O₂ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
59%	With palladium diacetate; tetraethylammonium hydroxide; tricyclohexylphosphine; In ethanol; toluene; at 110℃;	In a 500 mL round-bottomed flask, Compound 3(0.5 g, 1.76 mmol), Compound 4 (0.58 g, 2.64 mmol),Pd(OAc)2 (11.8 mg, 0.05 mmol) and tricyclohexylphosphine(29.5 mg, 0.1 mmol) were placed with AnhydrousToluene and Ethanol. It was raised to 110 C and(Et)4NOH was added to reaction flask. After reaction iscompleted, it is extracted by Chloroform and water. Afterremoving water from the mixture, it was filtered by usingMgSO4. The mixture was columned under MC:Hexane(1:4) mixed solvent. The product was concentrated underreduced pressure and re-precipitated with methanol toobtain pure solid material. The yield was 59%.

Reference： [1]Journal of Nanoscience and Nanotechnology,2015,vol. 15,p. 1850 - 1854

48
[ 572-83-8 ]
[ 1313615-33-6 ]
2-(3,4-dibutylthiophen-2-yl)anthracene-9,10-dione [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
56%	With tetrakis(triphenylphosphine) palladium⁽⁰⁾; potassium carbonate In toluene at 80℃; for 12h; Inert atmosphere;	2-(3,4-Dibutylthiophen-2-yl)anthracene-9,10-dione (3) To a solution of toluene (55 mL) and 1M K2CO3 solution (31.64 mL,31.64 mmol), added compound 1 (4.54 g, 15.82 mmol) and 2 (23.73 mmol). The solution was de-aerated at -78 C by three freeze-pump-thaw cycles. The solution was allowed to reach room temperature, then Pd(PPh3)4 (0.36 g, 0.32mmol) was added under N2 atmosphere. The reaction mixture was heated at 80 C for 12 h. After cooling down to room temperature, water and 2 mL concentrated HCl were added. The reaction mixture was extracted with methylene chloride,washed with brine, and dried over anhydrous MgSO4. The crude product was purified by column chromatography (n-hexane/ethyl acetate [50:1, v/v]) to afford the 3 as yellow solid. Yield: 3.60 g (56%);

Reference： [1]Shaik, Baji; Noh, Young Ri; Choi, Ho June; Yoon, Soon Byung; Yun, Myoung Hee; Kim, Jin Young; Lee, Sang-Gyeong [Bulletin of the Korean Chemical Society, 2015, vol. 36, # 4, p. 1215 - 1220]

49
[ 572-83-8 ]
[ 75-16-1 ]
C₁₆H₁₅Br [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
71%	In tetrahydrofuran; diethyl ether for 12h; Inert atmosphere; Reflux;	1 Synthesis of intermediate compound [1-1] The reaction flask of 2-bromo-anthraquinone 20g ( 69.66mmol ) , and the mixture was stirred into a 400mL anhydrous tetrahydrofuran at room temperature . nitrogenMethyl magnesium bromide in the atmosphere ( 1.4M in diethyl ether ) 149.3ml ( 208.98mmol ) was added dropwise slowly and reacted onThe temperature was raised to Figure stirred under reflux for 12 hours. Ethyl When the reaction is complete the reaction solution at room temperature was poured into 1N aqueous hydrochloric acid solutionAnd extracted with acetate . After the organic layer was separated and recrystallized with dichloromethane and methanol, the intermediate compound of yellow solid[1-1] to give the 14.1g ( 71 % ) .

Reference： [1]Current Patent Assignee: CS ELSOLAR - KR101536181, 2015, B1 Location in patent: Paragraph 0114; 0115

50
[ 108-86-1 ]
[ 572-83-8 ]
C₂₆H₁₉Br [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
47%	Stage #1: bromobenzene With n-butyllithium In tetrahydrofuran; hexane at -78℃; for 0.5h; Stage #2: 2-bromoanthracene-9,10-dione In tetrahydrofuran; hexane at 20℃; for 12h;	2 The reaction flask and stirred bromobenzene 24g (153.25mmol) in 300mL of anhydrous tetrahydrofuran. At -78 n- butyl lithium (2.5M in hexane) was added dropwise 61.3mL (153.25mmol) and 30 minutes later 2-bromo-anthraquinone 20g (69.66mmol) was slowly added as a solid and the reaction temperature to room temperature for 12 hours ups. After the reaction was terminated by extraction with ethyl acetate and a saturated aqueous solution of ammonium and the organic layer was separated, filtered, dried over anhydrous magnesium sulfate. Filtering the solution after concentration under reduced pressure the solid obtained was recrystallized with dichloromethane and hexane, 46.2g of potassium iodide 1 hydrate (278.64mmol) sodium teeth 59.1g (557.58mmol), and stirred under reflux into the acetic acid 200ml. The solid was filtered from the resulting intermediate compound After the reaction at room temperature and the light green yellow solid was recrystallized with dichloromethane and methanol, and [58-1] to give the 13.4g (47%).

Reference： [1]Current Patent Assignee: CS ELSOLAR - KR101536181, 2015, B1 Location in patent: Paragraph 0114; 0115

51
[ 572-83-8 ]
[ 474688-76-1 ]

Reference： [1]Patent: KR101528769,2015,B1
[2]Patent: KR101553561,2015,B1

52
[ 108-86-1 ]
[ 572-83-8 ]
[ 201731-79-5 ]

Yield	Reaction Conditions	Operation in experiment
93%	Stage #1: bromobenzene With n-butyllithium In tetrahydrofuran at -78℃; for 0.25h; Inert atmosphere; Stage #2: 2-bromoanthracene-9,10-dione In tetrahydrofuran at -78 - 20℃; for 1h;	1.1 500 ml three-neck bottle with magnetic stirringAfter Ar gas replacement, 3.9 g of bromobenzene (molecular weight 156, Ar, 0.025 mol) and 110 ml of THF were added in the above amounts in that order. Add BuLi15ml at -78 °C(2.5 M, 0.0375 mol), after completion, stirring for 15 minutes, keeping -78 ° C or less, and adding 2.25 g of 2-bromoindole (molecular weight 286, 99%, 0.0117 mol). After the addition, vigorously stir, naturally warm to room temperature, and stir at room temperature for 1 hrs.Add 200ml of water to hydrolyze, extract with ethyl acetate, evaporate the solvent, add 200ml of acetic acid, KI20g and sodium hypophosphite 20g, reflux, reaction for 1-2 hours, cool down, room temperature, precipitate, and filter to obtain pale yellow crude product The mixture was washed repeatedly with a mixture of THF and water to HPLC over 97% to give a pale-yellow product 4.44 g, molecular weight 408, yield 93%.
82%	Stage #1: bromobenzene With n-butyllithium In tetrahydrofuran; hexane at -78℃; for 1h; Stage #2: 2-bromoanthracene-9,10-dione In tetrahydrofuran; hexane at 20℃; for 12h; Stage #3: With acetic acid at 120℃; for 1h;	1.9 Synthesis of Intermediate 7-1 2.71 g (17.2 mmol) of bromobenzene was dissolved in 50 mL of THF, 6.9 mL (17.2 mmol, 2.5M in hexane) of nBuLi was slowly added thereto at a temperature of -78° C., and then, the resultant mixture was stirred for 1 hour. 2.16 g (7.5 mmol) of 2-bromo-4a,9a-dihydro-anthraquinone was slowly dropped to the reaction solution and then, the resultant reaction solution was stirred at room temperature for 12 hours. 50 mL of water was added to the reaction solution, the resultant solution was extracted there times by using 50 mL of ethylacetate, and then, the obtained organic layer was dried by using magnesium sulfate. 11.2 g (67.5 mmol) of KI and 10.6 g (82.5 mmol) of Na2H2PO2.H2O, which had been prepared by dissolving in 40 mL of an acetic acid, were added to the residual obtained by evaporating the solvent therefrom, and then, the resultant solution was stirred at a temperature of 120° C. for 1 hour. The reaction solution was cooled at room temperature, and then, 50 mL of water was added thereto, and filtered. The obtained residual was separation-purified by using silica gel column chromatography to obtain 5.77 g (yield: 82%) of Intermediate 7-1.
	Stage #1: bromobenzene With n-butyllithium In tetrahydrofuran at -78℃; for 1h; Inert atmosphere; Stage #2: 2-bromoanthracene-9,10-dione In tetrahydrofuran	1.2 Synthesis of Compound 1: Under nitrogen, 5.5 ml of bromobenzene was dissolved in 100 ml of anhydrous tetrahydrofuran,After cooling to -78 ° C, 45 ml of t-butyllithium was added dropwise. After the mixture was stirred for 1 hour, 2-bromoanthraquinone was added.An aqueous ammonium chloride solution was added, extracted with methylene chloride, dried, and the solvent was evaporated under reduced pressure. The product was dissolved in acetic acid, 19 g of potassium iodide and 20 g of NaH2PO2 were added and the mixture was refluxed for 3 hours. Filtration products,The product was washed with water and methanol to give compound 1.

Reference： [1]Current Patent Assignee: BEIJING ETERNAL MATERIAL TECHNOLOGY CO LTD - CN104649955, 2018, B Location in patent: Paragraph 0041; 0044; 0045
[2]Current Patent Assignee: Samsung Display (in: Samsung); SAMSUNG ELECTRONICS CO.,LTD. - KR2015/35331, 2015, A Location in patent: Paragraph 0213; 0214; 0231; 0232
[3]Current Patent Assignee: CHANGCHUN HAIPU RUNSI TECHNOLOGY CO LTD - CN106220571, 2016, A Location in patent: Paragraph 0044

53
[ 572-83-8 ]
[ 79887-11-9 ]
2-bromo-9,10-bis((4-hexylphenyl)ethynyl)anthracene [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
67.2%	Stage #1: 4-hexylphenylacetylene With isopropylmagnesium chloride In tetrahydrofuran at 60℃; Stage #2: 2-bromoanthracene-9,10-dione In tetrahydrofuran at 60℃; for 2h; Stage #3: With hydrogenchloride; tin(ll) chloride In tetrahydrofuran; water at 60℃;	1.1 Step 1: 2-bromo-9,10-bis ((4-hexylphenyl) ethynyl)anthracene (2-bromo-9,10-bis ((4-hexylphenyl) ethynyl) anthracene (DHPEA))Synthesis of Flask to 1-hexyl-4 - pentyl benzene (3.07 g, 16.5 mL) andthe mixture of tetrahydrofuran (THF) in 50 mL dissolved and then isopropylmagnesium chloride (8.3 mL, 16.5 mmol, 2 M in THF) was added to. After 60 eseo 30 bungan haon was heated to room temperature (23 ). 2-bromo-anthracene-9,10-dione (1 g, 3.5 mmol) was heated to60 until all of the solid disappears after adding the solution to beadded is dark brown (about 2 hours). After cooling again after the reaction toroom temperature, SnCl2 (4 g, 21 mmol) in 10mL 10% HCl were added and dissolvedslowly. After 30 more minutes the reaction was heated at 60 rapidly cooled to room temperature was added 400 mL of methanol. Filterthe precipitated orange solid, after washing with methanol and dried.Keolreomreul passed through a silica gel short length of a solid product was dissolvedin toluene (100m). Hexanes / toluene (1: 2, v / v) and recrystallized orangeobjective compound 2-bromo-9,10-bis ((4-hexylphenyl) ethynyl) anthracene wasobtained (DHPEA) a (1.68g, yield = 67.2%).

Reference： [1]Current Patent Assignee: GYEONGSANG NATIONAL UNIVERSITY - KR2016/101676, 2016, A Location in patent: Paragraph 0106-0109

54
[ 344-04-7 ]
[ 572-83-8 ]
C₂₆H₉BrF₁₀O₂ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
28.5 g	Stage #1: bromopentafluorobenzene With iodine; magnesium In tetrahydrofuran at 20℃; for 1h; Stage #2: 2-bromoanthracene-9,10-dione In tetrahydrofuran	1 Example 1 Next, under a nitrogen atmosphere, magnesium (2.9 g, 120 mmol), tetrahydrofuran (THE) (210 ml) and a small amount of iodine were added in a reactor, and the compound represented by the aforementioned formula (5) (30 g, 120 mmol) was added dropwise therein at an internal temperature of 20° C. or less. Thereafter, the reaction solution was stirred for 1 hour while maintaining an internal temperature of 20° C. or less. Then, the compound represented by the following formula (6) (14.5 g, 50 mmol) was added therein, and the reaction solution was further stirred overnight. Thereafter, hydrochloric acid (2 N, 140 ml) was added dropwise therein, to thereby terminate the reaction, and the reaction solution was extracted with ethyl acetate (200 ml). Thereafter, the extracted solution was washed with a saturated saline solution and water. Then, anhydrous magnesium sulfate was added therein, and the solution was stirred for 1 hour. Thereafter, the solution was filtrated, and the obtained filtrate was concentrated under a reduced pressure, to thereby obtain the compound represented by the following formula (7) (28.5 g).

Reference： [1]Current Patent Assignee: TOSHIBA CORPORATION - US2016/351828, 2016, A1 Location in patent: Paragraph 0135

55
[ 572-83-8 ]
3-(3,4-ethylenedioxythiophene)prop-1-yne [ No CAS ]
2-(3-(2,3-dihydrothieno[3,4-b][1,4]dioxin-2-yl)prop-1-yn-1-yl)anthracene-9,10-dione [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
65%	With copper(l) iodide; tetrakis(triphenylphosphine) palladium⁽⁰⁾; triethylamine In tetrahydrofuran at 75℃; for 0.5h; Inert atmosphere;	2-(3-(2,3-Dihydrothieno[3,4-b][1,4]dioxin-2-yl)prop-1-yn-1-yl)anthracene-9,10-dione(12). In a heavy-walled Smith process vial (25 mL) 2-bomoanthraquinone (300 mg, 1.05mmol) and pyEDOT (207 mg, 1.15 mmol) were dissolved in dry THF (15 mL). The solutionwas then degassed with nitrogen over 30 minutes. CuI (20 mg, 0.104 mmol), Pd(PPh3)4 (36mg, 0.031 mmol) and TEA (0.3 mL, 2.09 mmol) were consecutively added. The vial wassealed with a Teflon cap under nitrogen atmosphere, and heated at 75 °C in an oil bathovernight. The resulting black slurry was filtered through a pad of celite by suction filtration.The filtrate was concentrated under vacuum, affording the crude product as a black-brownsolid. This solid was purified through column chromatography (SiO2; pentane/DCM, 1:2) toafford pyEDOT derivative 12 as a yellow solid, mp 165-169 °C. (290 mg, 65%). 1H NMR (499.93 MHz, CDCl3, 25 °C) δ = 8.33 - 8.30 (m, 3H, H-14,23,26), 8.26 (dd, J = 0.5, 8.0 Hz,1H, H-17), 7.81 (m, 2 H, H-24,25), 7.79 (dd, J = 1.7, 8.0 Hz, 1H, H-18), 6.38 (d, J = 3.6 Hz,1H, H-1/4), 6.37 (d, J = 3.6 Hz, 1H, H-1/4), 4.43 (m, 1H, H-8), 4.37 (dd, J = 2.2, 11.6 Hz, 1H,H-7), 4.15 (dd, J = 7.1, 11.6 Hz, 1H, H-7’), 2.97 (dd, J = 5.5, 17.2 Hz, 1H, H-12), 2.88 (dd, J= 7.9, 17.2 Hz, 1H, H-12’). 13C NMR (125.7 MHz, CDCl3, 25 °C): δ = 182.7 (C-19), 182.6(C-22), 141.4 (C-2/3), 141.3 (C-2/3), 136.8 (C-18), 134.5 (C-24/25), 134.4 (C-24/25), 133.6(C-20/21), 133.5 (C-20/21), 133.5 (C-15), 132.6 (C-16), 130.5 (C-14), 129.4 (C-13), 127.5(C-23/26), 127.4 (C-23/26), 100.2 (C-1/4), 100.1 (C-1/4), 89.3 (C-10), 82.3 (C-11), 71.8 (C-8), 67.4 (C-7), 22.3 (C-12). IR (neat, /cm-1): 2919, 1672, 1591, 1485, 1304, 709. APCI-MS:387.59 (M+H+). HRMS, calculated for C23H15O4S: m/z = 387.06856, found: m/z = 387.06828([M + H+]).

Reference： [1]Huang, Xiao; Yang, Li; Emanuelsson, Rikard; Bergquist, Jonas; Strømme, Maria; Sjödin, Martin; Gogoll, Adolf [Beilstein Journal of Organic Chemistry, 2016, vol. 12, p. 2682 - 2688]

56
[ 648905-68-4 ]
[ 572-83-8 ]
C₂₅H₂₂O₅S [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
94%	With tetrakis(triphenylphosphine) palladium⁽⁰⁾; potassium carbonate In ethanol; water; toluene at 115℃; for 3h; Inert atmosphere;	Synthesis of 2-sulfophenyl anthracene precursor 2-Sulfophenyl anthraquinone(2-SPAQ) precursor was synthesized according to established procedure.S7 Toluene (100mL), ethanol (20 mL) and 1M K2CO3 solution (30 mL) were added to a mixture ofneopentyl 4-(4,4,5,5-tetramethyl-1,3-dioxaboran-2-yl)benzenesulfonate (1.06 g, 3.00mmol), 2-anthraquinoneboronic acid (0.858 g, 3.00 mmol) andtetrakis(triphenylphosphine) palladium (0) (0.104 g, 9.00×10-2 mmol) under N2atmosphere. The reaction mixture was refluxed at 115 °C and stirred for 3 hours. Then,the mixture was concentrated in vacuo, extracted with chloroform, washed with waterand brine, and dried over anhydrous Na2SO4. The product was purified with columnchromatography (silica gel, 1,2-dichloroethane) to give 2-sulfophenyl anthraquinoneprecursor (1.23 g, 94%) as a pale yellow solid. 1H NMR (400MHz, CDCl3). δ 8.58 (d,J1 = 1.6 Hz, 1H, Ar-H), δ 8.45 (d, J1 = 7.4 Hz, 1H, Ar-H), δ 8.37 (m, 2H, Ar-H), 8.07 (m,3H, Ar-H), 7.92 (d, J1 = 8.0 Hz, 2H, Ar-H), 7.85 (m, 2H, Ar-H), 3.76 (s, 2H, CH2), 0.96(s, 9H, CH3) ppm.

Reference： [1]Miyano, Tetsuya; Hisaki, Ichiro; Tohnai, Norimitsu [Chemistry Letters, 2017, vol. 46, # 2, p. 225 - 227]

57
[ 572-83-8 ]
[ 597553-98-5 ]

Reference： [1]Patent: CN106220571,2016,A
[2]Patent: CN104649955,2018,B

58
[ 572-83-8 ]
[ 78600-31-4 ]
2’-bromo-10,10’’-diphenyl-10 H,10’’H-dispiro[acridine-9,9’-anthracene-10’,9’’-acridine] [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
85%		After dissolving 2-bromo-N, N-diphenylaniline (20 g, 61.68 mmol) in THF (250 ml), the temperature was lowered to -78 C.,After adding BuLi (34.5 ml) dropwise, 30 minutes later, 2-bromoanthracene-9,10-dione (17.7 g, 61.68 mmol)Followed by stirring RT for 1 hour. Add 1N HCl (300 ml) and filter. After washing with ethyl acetate, chloroform and Recrystallization; resulting solid was placed in acetic acid (250 ml), 2 ml of sulfuric acid was added dropwise, and the mixture was refluxed with stirring. The temperature was lowered to room temperature and water, And the filtered solid was recrystallized from ethyl acetate to give Compound A1 (38.9 g, 85%).

Reference： [1]Patent: KR2017/41648,2017,A .Location in patent: Paragraph 0117-0121

59
[ 902518-11-0 ]
[ 572-83-8 ]
C₅₀H₂₉BrN₂ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
85%		9- (2-bromophenyl) -9H-carbazole (20 g, 62.07 mmol)Was dissolved in THF (250 ml), the temperature was lowered to -78 ° C, 2.5M n-BuLi (34.7 ml) was added dropwise, and after 30 minutes, 2-bromoanthracene-9,10-dione (17.7 g, 61.68 mmol) And the mixture was stirred at RT for 1 hour. Add 1N HCl (300 ml) and filter. Washed with ethyl acetate, and then recrystallized from chloroform and ethyl acetateThe obtained solid was dissolved in acetic acid (250 ml), 2 ml of sulfuric acid was added dropwise, and the mixture was refluxed with stirring. The temperature was lowered to room temperature and neutralized with water. The filtered solid was recrystallized from ethyl acetate to give Compound A1 (38.9 g, 85percent).

Reference： [1]Patent: KR2017/41647,2017,A .Location in patent: Paragraph 0108-0112

60
[ 654067-65-9 ]
[ 572-83-8 ]
2-(4-(di-p-tolylamino)phenyl)anthracene-9,10-dione [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
85.59%	Stage #1: [4-[bis(4-methylphenyl)amino]phenyl]boronic acid; 2-bromoanthracene-9,10-dione With teterabutylammonium; potassium carbonate In toluene at 20℃; for 0.25h; Inert atmosphere; Stage #2: With tetrakis(triphenylphosphine) palladium⁽⁰⁾ In toluene for 12h; Reflux; Inert atmosphere;	1 2.3.1 Synthesis of 4,4'-((4-(9,10-dioxo-9,10-dihydroanthracen-2-yl)phenyl)azanediyl)dibenzaldehyde (dye 1) General procedure: Compound 7 (0.38 g, 1.0 mmol), 10 (0.44 g, 1.3 mmol), tetrabutylammonium (0.16 g, 0.5 mmol) were dissolved in toluene (40 mL) under argon, and K2CO3 (2 M, 2.5 mL) was added. The mixture was stirred at room temperature for 15 min, and then Pd(PPh3)4 catalyst (0.05 g, 0.04 mmol) was added. The reaction mixture was heated to reflux for 12 h. After cooling, the product was extracted with CH2Cl2, washed with water, dried over anhydrous MgSO4. The organic layer was evaporated and the compound was purified by flash chromatography on silica gel column (petroleum ether:ethyl acetate = 10:1 as eluent) to give orange solid 0.28 g, yield: 54.90%, m.p. 182-183 °C.

Reference： [1]Li, Yanxia; Tan, Tingfeng; Wang, Shirong; Xiao, Yin; Li, Xianggao [Dyes and Pigments, 2017, vol. 144, p. 262 - 270]

61
[ 201802-29-1 ]
[ 572-83-8 ]
2‐(4‐(bis(4-methoxyphenyl)amino)phenyl)anthracene-9,10-dione [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
91%	With caesium carbonate In tetrahydrofuran; water; N,N-dimethyl-formamide at 100 - 180℃; for 29h; Irradiation;	1-3 A method for preparing a fluorescent compound for tertiary oil chemistry viscous viscosity detection, comprising the steps of: (1) 286 mg of 2-bromoindole-9,10-dione was dissolved in 100 mL of dry THF in water, and stirred by ultrasonic to obtain a solution 1;(2) Dissolve 1745 mg of (4-(bis(4-methoxyphenyl)amino)phenyl)boronic acid in 500 mL of dry water-removed DMF, and stir evenly to obtain a solution 2(3) simultaneously dissolving 3.26 g of cesium carbonate in deionized water and uniformly stirring by ultrasonic to obtain a 5 mol/L aqueous solution of Cs2CO3 (solution 3);(4) The solution 1 of the step (1) and the solution 2 of the step (2) are mixed, uniformly mixed, and 106 mg of a palladium catalyst is added thereto, and a vacuum is applied to perform a heating reaction to control the reaction temperature to 100 ° C. After reacting for 5 hours, a 5 mol/L Cs2CO3 aqueous solution (solution 3) obtained in the step (3) was added dropwise thereto, followed by a second heating reaction, and the reaction temperature was controlled at 180 ° C. After the reaction was continued for 24 hours, the reaction was cooled to room temperature. The organic phase was extracted with ethyl acetate and dried over anhydrous sodium sulfate. The solvent was evaporated under reduced pressure and purified by silica gel column chromatography eluting with methylene chloride: methanol: V/V=20/1 And neutral alumina column (purified by dichloromethane to ethyl acetate: V / V = 1 / 1), to obtain 465.0mg dark red solid powder 2- (4- (double (4- Oxyphenyl)amino)phenyl)indole-9,10-dione (fluorescent compound used for the detection of viscosity in tertiary oil chemistry) with a yield of 91%. The characterization of the fluorescent compound obtained for the third-stage oil chemistry chemical viscosity measurement in this example is the same as that characterization in Example 1, and reference can be made to FIGS. 2 and 3.
90.02%	Stage #1: N,N'-bis(4-methoxyphenyl)-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)aniline; 2-bromoanthracene-9,10-dione With teterabutylammonium; potassium carbonate In toluene at 20℃; for 0.25h; Inert atmosphere; Stage #2: With tetrakis(triphenylphosphine) palladium⁽⁰⁾ In toluene for 12h; Reflux; Inert atmosphere;	1 2.3.1 Synthesis of 4,4'-((4-(9,10-dioxo-9,10-dihydroanthracen-2-yl)phenyl)azanediyl)dibenzaldehyde (dye 1) General procedure: Compound 7 (0.38 g, 1.0 mmol), 10 (0.44 g, 1.3 mmol), tetrabutylammonium (0.16 g, 0.5 mmol) were dissolved in toluene (40 mL) under argon, and K2CO3 (2 M, 2.5 mL) was added. The mixture was stirred at room temperature for 15 min, and then Pd(PPh3)4 catalyst (0.05 g, 0.04 mmol) was added. The reaction mixture was heated to reflux for 12 h. After cooling, the product was extracted with CH2Cl2, washed with water, dried over anhydrous MgSO4. The organic layer was evaporated and the compound was purified by flash chromatography on silica gel column (petroleum ether:ethyl acetate = 10:1 as eluent) to give orange solid 0.28 g, yield: 54.90%, m.p. 182-183 °C.

Reference： [1]Current Patent Assignee: SOUTH CHINA UNIVERSITY OF TECHNOLOGY - CN110272350, 2019, A Location in patent: Paragraph 0052-0070
[2]Li, Yanxia; Tan, Tingfeng; Wang, Shirong; Xiao, Yin; Li, Xianggao [Dyes and Pigments, 2017, vol. 144, p. 262 - 270]

62
[ 572-83-8 ]
[ 214360-73-3 ]
[ 856357-68-1 ]

Yield	Reaction Conditions	Operation in experiment
70.23%	Stage #1: 2-bromoanthracene-9,10-dione; 4-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)aniline With teterabutylammonium; potassium carbonate In toluene at 20℃; for 0.25h; Inert atmosphere; Stage #2: With tetrakis(triphenylphosphine) palladium⁽⁰⁾ In toluene for 12h; Reflux; Inert atmosphere;	1 2.3.1 Synthesis of 4,4'-((4-(9,10-dioxo-9,10-dihydroanthracen-2-yl)phenyl)azanediyl)dibenzaldehyde (dye 1) General procedure: Compound 7 (0.38 g, 1.0 mmol), 10 (0.44 g, 1.3 mmol), tetrabutylammonium (0.16 g, 0.5 mmol) were dissolved in toluene (40 mL) under argon, and K2CO3 (2 M, 2.5 mL) was added. The mixture was stirred at room temperature for 15 min, and then Pd(PPh3)4 catalyst (0.05 g, 0.04 mmol) was added. The reaction mixture was heated to reflux for 12 h. After cooling, the product was extracted with CH2Cl2, washed with water, dried over anhydrous MgSO4. The organic layer was evaporated and the compound was purified by flash chromatography on silica gel column (petroleum ether:ethyl acetate = 10:1 as eluent) to give orange solid 0.28 g, yield: 54.90%, m.p. 182-183 °C.

Reference： [1]Li, Yanxia; Tan, Tingfeng; Wang, Shirong; Xiao, Yin; Li, Xianggao [Dyes and Pigments, 2017, vol. 144, p. 262 - 270]

63
[ 572-83-8 ]
[ 544-97-8 ]
2-bromo-9,9,10,10-tetramethyl-9,10-dihydroanthracene [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
50%	Stage #1: dimethyl zinc(II) With titanium tetrachloride In dichloromethane at -40℃; for 0.333333h; Stage #2: 2-bromoanthracene-9,10-dione In dichloromethane at 20℃;	Synthesis of 2-bromo-9,9,10,10-tetramethyl-9,10-dihydroanthraquinone Titanium (IV) chloride (62.7 ml, 62.7 mmol) was added to a dry three-neck round bottom flask. The solution was degassed under N2 and cooled to -40 °C. Dimethylzinc (50.2 ml, 100 mmol) was added dropwise. Stir the mixture at the same temperature20min. It will then be added dropwise to 250 mL DCM.2-bromostilbene-9,10-dione (3.6 g, 12.54 mmol). The reaction mixture was allowed to warm to room temperature and stirred overnight. The reaction flask was cooled to 0 °C and quenched with MeOH. The mixture was diluted with water and extracted with DCM. The combined organic phases were washed with brine. After removal of the solvent, the crude product was adsorbed on celite and purified by flash chromatography (heptane) to give 2-bromo-9,9,10,10-tetramethyl-9,10-dihydroanthracene (2 g, 50 %).

Reference： [1]Current Patent Assignee: UNIVERSAL DISPLAY CORP - CN107868109, 2018, A Location in patent: Paragraph 0254-0256

64
[ 572-83-8 ]
[ 122-39-4 ]
N-(anthraquinone-2-yl)-N,N-diphenylamine [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
68%	With palladium diacetate; potassium carbonate In dimethyl sulfoxide at 120℃; for 24h; Inert atmosphere;	2.1.1. Synthesis of monomer DPA-AQ [32] Under a nitrogen atmosphere, diphenylamine (1.694 g,10 mmol), 2-bromoanthraquinone (4.305 g, 15 mmol), potassium carbonate (2.072 g, 15 mmol), and dimethyl sulfoxide (45 mL) were successively added to a dry three-neck flask. Then Pd(OAc)2(115 mg, 0.5 mmol) was added and the reaction was carried out at 120 °C for 24 h. After cooling to room temperature, the reaction solution was added dropwise to a saturated ammonium chloride solution, separated by suction filtration, and the solid was washed with water until neutral. Drying at 80 °C for 24 h gives a red crude product which was purified by column chromatography on silica gel/petroleum ether and dichloromethane (v/v 3:1) to give the final product as an orange-red solid powder (2.562 g, 68%). 1H NMR(500 MHz, CDCl3, δ): 7.19 (s, 2H), 7.21-7.22 (m, 4H), 7.25-7.27 (dd,1H), 7.35-7.38 (m, 4H), 7.71-7.78 (m, 3H), 8.11-8.12 (d, 1H),8.21-8.23 (dd, 1H), 8.28-8.30 (dd, 1H). 13C NMR (125 MHz, CDCl3, δ): 116.95, 124.31, 125.70, 126.26, 126.45, 127.08, 128.28, 129.28,130.03, 133.63, 134.10, 135.02, 137.12, 145.12, 145.74, 152.93, 181.73,183.52. FT-IR (KBr, v): 3057, 1672, 1568, 1487, 1323, 715.

Reference： [1]Huang, Wanrong; Jia, Tao; Zhou, Guangying; Chen, Sha; Hou, Qiong; Wang, Yuhai; Luo, Suilian; Shi, Guang; Xu, Bingjia [Electrochimica Acta, 2018, vol. 283, p. 1284 - 1290]

65
[ 108-86-1 ]
[ 572-83-8 ]
2-bromo-10,10-diphenyl-10H-anthrone [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
65%	Stage #1: bromobenzene With magnesium In tetrahydrofuran at 65℃; for 3h; Inert atmosphere; Reflux; Stage #2: 2-bromoanthracene-9,10-dione In tetrahydrofuran for 3h; Reflux;	2 Metal magnesium (0.21 mol) was added to a 1 L three-necked flask equipped with a constant pressure dropping funnel.Bromobenzene (0.20 mol) was dissolved in 300 mL of tetrahydrofuran, placed in a constant pressure dropping funnel, and protected with nitrogen. The three-necked flask was heated to a temperature of 65 ° C, and a tetrahydrofuran solution of bromobenzene was added through a constant pressure dropping funnel. First, add 50mL, after the reaction is initiated, slowly drop the remaining part, complete the dropwise addition in 1h, react at reflux temperature for 2h, transfer to room temperature and transfer to a constant pressure funnel for use;2 - bromo anthraquinone(0.080 mol) was dissolved in 200 mL of tetrahydrofuran and added to a 2 L three-necked flask, and then the above-mentioned standby solution was slowly added dropwise, and reacted at reflux temperature for 3 hours. After the reaction was completed, the temperature was lowered to 25 ° C, and the above reaction was carried out. The solution was slowly poured into 200 g of dilute hydrochloric acid having a mass concentration of 10%, stirred for 15 min, and liquid-separated, the organic phase was collected, the solvent was removed under reduced pressure, and the material was obtained by column chromatography to give the material A2, HPLC purity 99.5%, yield 65%;

Reference： [1]Current Patent Assignee: VALIANT CO., LTD. - CN108250145, 2018, A Location in patent: Paragraph 0066; 0067; 0068; 0069; 0070

66
[ 572-83-8 ]
4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-N-(4-hydroxyphenyl)diphenylamine [ No CAS ]
2-(N-(4-hydroxyphenyl)diphenylamino)-4′-anthraquinone [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
75%	With tetrakis(triphenylphosphine) palladium⁽⁰⁾; potassium carbonate In water; toluene at 100℃; for 24h; Inert atmosphere;
75%	With tetrakis(triphenylphosphine) palladium⁽⁰⁾; potassium carbonate In water; toluene for 24h; Inert atmosphere;

Reference： [1]Yang, Yun; Zhao, Lei; Wang, Shumeng; Ding, Junqiao; Wang, Lixiang [Macromolecules, 2018]
[2]Yang, Yun; Zhao, Lei; Wang, Shumeng; Ding, Junqiao; Wang, Lixiang [Macromolecules, 2018, vol. 51, # 23, p. 9933 - 9942]

67
[ 572-83-8 ]
C₂₇H₂₀B₂N₂O₄ [ No CAS ]
C₅₅H₃₀N₂O₄ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With tetrakis(triphenylphosphine) palladium⁽⁰⁾; potassium carbonate In acetone at 100 - 120℃; for 5h; Inert atmosphere;	3 (3) Compound L41 Slowly join the three-necked bottle with A under the protection of N2Pd(PPh3)4 (Chinese name: tetrakis-(triphenylphosphine)-palladium (0) compound), K2CO3,Acetone mixed solution,Then, after slowly adding a certain amount of D compound,The mixture was slowly heated to 100 to 120 ° C for 5 hours until the mixture was sufficiently chemically reacted. then,After cooling the mixture to room temperature,Rinse with ether,The organic phase is rinsed with salt water,Then, it is sufficiently dried with magnesium sulfate to remove the solvent.The final product obtained,The column was passed through a column (pre-organic phase was toluene/n-hexane = 1:1,The later organic phase was a toluene/n-hexane solution = 2:1) to obtain a product L41 having a purity of 98% or more.To further increase the purity of L41,Sublimation by one or more times using a vacuum sublimation instrument,L41 products with a purity greater than 99.0% can be obtained.Using CDCL3 as a solvent,Tetramethylsilane (δ = 0.00 ppm) was recorded as an internal standard 1H NMR spectrum.

Reference： [1]Current Patent Assignee: AAC ACOUSTIC TECHNOLOGIES HOLDINGS INC. - CN108822088, 2018, A Location in patent: Paragraph 0076; 0077; 0078

68
[ 572-83-8 ]
[ 292638-85-8 ]
(E)-methyl 3-(9,10-dioxo-9,10-dihydroanthracen-2-yl)acrylate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
93%	With sodium acetate; palladium diacetate In 1-methyl-pyrrolidin-2-one at 115℃; for 17h; Inert atmosphere;	4 4.1.4 (E)-Methyl 3-(9,10-dioxo-9,10-dihydroanthracen-2-yl)acrylate (5) To an oven dried round bottomed flask, charged with a magnetic stir bar were added 2-bromoanthraquinone (2.0 g, 7.0 mmol), methyl acrylate (0.88 ml), NaOAc (0.62 g, 7.6 mmol) and Pd(OAc)2 (0.62 mg, 0.00279 mmol) in NMP (50 mL) under argon atmosphere. The reaction flask was fitted with a reflux condenser, heated to 115 °C and stirred overnight under argon atmosphere. After completion, the reaction mixture was cooled to room temperature and extracted with ethyl acetate. The organic layer was washed with water, dried over Na2SO4, and concentrated under reduced pressure to afford compound 5 in 93% yield. 1H NMR (500 MHz, CDCl3) δ 8.41 (s, 1H), 8.30 (d, J = 6.3 Hz, 3H), 7.87 (d, J = 7.4 Hz, 1H), 7.79-7.75 (m, 3H), 6.64 (d, J = 16.0 Hz, 1H), 3.84 (s, 3H). 13C NMR (125 MHz, CDCl3) δ 182.7, 182.5, 166.7, 142.5, 140.0, 134.5, 134.4, 134.0, 133.9, 133.5, 133.4, 133.0, 128.1, 127.5, 127.4, 126.6, 121.8, 52.2 ESI MS (m/z) = 293.08 [M+H]+.

Reference： [1]Song, Yoojin; Lim, Jiah; Seo, Young Ho [European Journal of Medicinal Chemistry, 2019, vol. 164, p. 263 - 272]

69
[ 572-83-8 ]
9,9,9'9'-tetramehtyl-9,9'10,10'-tetrahydro-2,10'-biacridine [ No CAS ]
C₄₄H₃₄N₂O₂ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
37%	With tris-(dibenzylideneacetone)dipalladium⁽⁰⁾; tri-tert-butyl phosphine; sodium t-butanolate In toluene for 24h; Reflux; Inert atmosphere;	3 Preparation of Compound M4: Add 2,10'-biacidine (189 mg, 0.4528 mmol) and 2-bromoindole (100 mg, in sequence) to a 100 mL two-necked vial.0.3483mmol),Tri-tert-butylphosphine (5.64 mg, 27.86 μmol),Sodium tert-butoxide (134 mg, 1.393 mmol),Tris(dibenzylideneacetone)dipalladium (12.7 mg, 13.93 mmol)And toluene (60mL),The mixture was refluxed under nitrogen for 24 h.After the reaction solution is cooled to room temperature,The mixture was extracted with CH 2 Cl 2 (3×30 mL);The organic layer was washed successively with water (50 mL).Drying and distilling off the solvent under reduced pressure.Residue with petroleum ether: dichloromethane (V: V = 5: 1)Separation of red for eluent column chromatographyColor solid 80 mg (yield: 37%).

Reference： [1]Current Patent Assignee: XIANGTAN UNIVERSITY - CN109096252, 2018, A Location in patent: Paragraph 0056; 0057; 0058; 0065; 0066

70
[ 109-04-6 ]
[ 572-83-8 ]
C₂₄H₁₇BrN₂O₂ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Stage #1: 2-bromo-pyridine With tert.-butyl lithium In tetrahydrofuran; pentane at -78℃; for 1h; Inert atmosphere; Stage #2: 2-bromoanthracene-9,10-dione In tetrahydrofuran; pentane at 20℃; for 4h;	1 Example 1: Synthesis of Compound (A-1) 2-Bromopyridine (0.8 g, 5.3 mmol) was dissolved in anhydrous tetrahydrofuran (10 mL), and the mixture was evaporated in vacuo to remove oxygen, and the temperature was lowered to -78 ° C under nitrogen atmosphere, and t-butyl lithium (4.7 mL) was slowly added dropwise. , 1.7 M pentane solution), maintaining the temperature for further 1 hour, adding the compound (S-2) (0.7 g, 2.5 mmol), stirring was continued for 1 hour, the temperature was naturally raised to room temperature, stirred for 3 hours, and an aqueous solution of ammonium chloride was added. The organic phase was combined and dried over anhydrous magnesium sulfate and the solvent was evaporated to give intermediate (S-3).

Reference： [1]Current Patent Assignee: AAC ACOUSTIC TECHNOLOGIES HOLDINGS INC. - CN109705108, 2019, A Location in patent: Paragraph 0089; 0090; 0091

71
[ 572-83-8 ]
[ 117-79-3 ]
2,2′,2″-nitrilotris(anthracene-9,10-dione) [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
50%	With dicyclohexyl-(2',6'-dimethoxybiphenyl-2-yl)-phosphane; tris-(dibenzylideneacetone)dipalladium(0); sodium t-butanolate; In toluene; at 100℃; for 48h;Inert atmosphere; Schlenk technique;	mixture of <strong>[117-79-3]2-aminoanthracene-9,10-dione</strong> (223 mg, 1 mmol, 85%purity), 2-bromoanthracene-9,10-dione (718 mg, 2.5 mmol), Pd2(dba)3(80 mg, 0.08 mmol), 2-dicyclohexylphosphino-2?,6?-dimethoxybiphenyl(SPhos, 50 mg, 0.12 mmol) and t-BuONa (300 mg, 3.1 mmol) in 20 mltoluene was stirred under N2 atmosphere at 100 C for 2 days. Back toroom temperature, the solvent was removed by reduced pressure. Thecrude product was purified by column chromatography on silica gel byusing CH2Cl2 as eluent to afford 2,2?,2?-nitrilotris(anthracene-9,10-dione) (NAQ3) as an orange-red solid. Yield: 317 mg, 50%. 1H NMR(400 MHz, CDCl3, delta): 8.35-8.32 (m, 6H), 8.26 (d, J=8.0 Hz, 3H), 8.02(s, 3H), 7.81 (q, J=8.0 Hz, 6H), 7.56 (d, J = 8.0 Hz, 3H); High-resolutionESI mass spectrum Calcd. [M + Na, C42H21NO6Na]+:658.1267, Found: [M+Na]+ 658.1270.

Reference： [1]Organic electronics,2019,vol. 73,p. 102 - 108

72
[ 572-83-8 ]
[ 133113-76-5 ]
C₂₀H₁₁BrS₄ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
78%	Stage #1: dimethyl (1,3-dithiol-2-yl)phosphonate With n-butyllithium In tetrahydrofuran; hexane at -78℃; for 0.666667h; Inert atmosphere; Stage #2: 2-bromoanthracene-9,10-dione In tetrahydrofuran; hexane at -78 - 20℃; for 20h; Inert atmosphere;

Reference： [1]Skaisgirski, Michael; Larsen, Christopher B.; Kerzig, Christoph; Wenger, Oliver S. [European Journal of Inorganic Chemistry, 2019]

73
[ 572-83-8 ]
3,6-di-tert-butyl-1-(2,4,6-trimethylphenyl)-9H-carbazole [ No CAS ]
C₄₃H₄₁NO₂ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
89%	With palladium diacetate; sodium t-butanolate; tri tert-butylphosphoniumtetrafluoroborate In toluene at 110℃; for 24h; Schlenk technique;	3 1-(2,4,6-trimethyl)phenyl-3,6-di-tert-butylcarbazole (0.24 g, 0.6 mmol), 2-bromoindole(0.14 g, 0.5 mmol), palladium acetate (5.6 mg, 0.025 mmol), tri-tert-butylphosphine tetrafluoroborate (14.5 mg, 0.05 mmol), sodium tert-butoxide (96.1 mg, 1 mmol) added to 50 ml of Schlenk To the flask, toluene (10 mL) was added, and the reaction was refluxed at 110 ° C for 24 h.After completion of the reaction, it was cooled to room temperature, and the reaction mixture was poured into water, and extracted three times with dichloromethane, and the organic phase was combined.The organic phase was washed three times with 30 ml of water and dried over anhydrous sodium sulfate.The solution was filtered and concentrated.Separation by a silica gel column gave 0.27 g of a red solid, yield 89%..

Reference： [1]Current Patent Assignee: CHINESE ACADEMY OF SCIENCES - CN109810097, 2019, A Location in patent: Paragraph 0110; 0115; 0116; 0117

74
[ 572-83-8 ]
[ 917-54-4 ]
[ 103438-64-8 ]

Yield	Reaction Conditions	Operation in experiment
44%	Stage #1: 2-bromoanthracene-9,10-dione; methyllithium In tetrahydrofuran at -78 - 20℃; Inert atmosphere; Darkness; Stage #2: With hydrogenchloride; tin(II) chloride dihdyrate In tert-butyl methyl ether at 20℃; for 3.5h; Cooling with ice;	Preparation of 2-bromo-9,10-dimethylanthracene (35-2) In a 4-neck 10 L flask, 2-bromoanthraquinone (compound 35-1, 500 g, 1.74 mole) was dissolved in anhydrous THF (6.5 L). The solution was cooled to -78° C. under nitrogen atmosphere and MeLi (2.39 L, 3.83 mole) was added dropwise over 2 h. The darkened reaction mixture was stirred for another 1 h at -78° C. and then was allowed to reach room temperature overnight. The reaction was quenched with saturated NH4Cl (1.5 L). The organic layer was separated, washed with H2O, dried over anhydrous Na2SO4, and concentrated under reduced pressure. The resulting yellow solid was then dissolved in MTBE (3.4 L). A solution of SnCl2.2H2O (2.12 kg, 9.40 mole) in concentrated HCl (1.67 L) was added under ice bath cooling over 30 min. The reaction mixture was stirred for 3 h at room temperature, then transferred to a separatory funnel, washed with H2O, dried over anhydrous sodium sulfate, and concentrated under reduced pressure. The residue was purified by column chromatography (SiO2, eluent: petroleum ether/DCM 20:1) to give the title compound 35-2 (220 g, 44%) as a yellow solid.

Reference： [1]Current Patent Assignee: PROFUSA INC - US2020/383, 2020, A1 Location in patent: Paragraph 0561-0562

75
[ 572-83-8 ]
[ 867044-28-8 ]

Reference： [1]Patent: KR101553561,2015,B1

76
[ 572-83-8 ]
[ 204530-94-9 ]
C₄₆H₃₁BrO₂ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
		While stirring a 1 L round bottom flask, 88.8 g (0.313 mol) of 1-bromo-4(1'-naphthyl)benzene and 200 ml of THF were added.After the temperature was dropped to -78 C, 20.5 ml (0.313 mol) of n-BuLi was slowly added dropwise.After the dropwise addition, the mixture was stirred for 1 hour and 30 minutes, and 30.0 g (0.104 mol) of 2-bromoanthraquinone was dissolved in 100 ml of THF and rapidly added.After standing for 10 minutes, the mixture was stirred at room temperature for 1 day.When the reaction was completed, 150 ml of 2N hydrochloric acid was added to make it acidic, and concentrated.The concentrated reaction was placed in a 500 ml round-bottom flask, KI 52.04 g (0.313 mol), NaH2PO2H2O 66.45 g (0.627 mol),It was refluxed with 300 ml of acetic acid for 3 hours. Upon completion of the reaction, the mixture was lowered to room temperature, and the resulting solid was filtered, washed with methanol, and determined with toluene.As a result, 41.6 g (0.063 mol, yield 60.2%) of an ocher solid was obtained.

Reference： [1]Patent: KR101553561,2015,B1 .Location in patent: Paragraph 0226-0230

77
[ 591-17-3 ]
[ 572-83-8 ]
C₂₈H₂₃BrO₂ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Stage #1: meta-bromotoluene With n-butyllithium In tetrahydrofuran at -78℃; for 1.5h; Stage #2: 2-bromoanthracene-9,10-dione In tetrahydrofuran at 20℃; for 24h; Stage #3: With hydrogenchloride In tetrahydrofuran; water	8.8-1 Synthesis Example 8- (1): Synthesis of 2-bromo-9,10-di (3'-methylphenylanthracene While stirring the 1L round bottom flask, 53.6 g (0.313 mol) of 3-bromotoluene and 200 ml of THF were added.After the temperature was dropped to -78 ° C, 20.5 ml (0.313 mol) of n-BuLi was slowly added dropwise.After the dropwise addition, the mixture was stirred for 1 hour and 30 minutes, and 30.0 g (0.104 mol) of 2-bromoanthraquinone was dissolved in 100 ml of THF and rapidly added.After standing for 10 minutes, the mixture was stirred at room temperature for 1 day. When the reaction ends,150 ml of 2N hydrochloric acid was added to make it acidic, and concentrated.The concentrated reaction was placed in a 500 ml round bottom flask, 52.04 g (0.313 mol) of KI, 66.45 g (0.627 mol) of NaH2PO2H2O,It was refluxed with 300 ml of acetic acid for 3 hours. Upon completion of the reaction, it was lowered to room temperature,The resulting solid was filtered, washed with methanol, and recrystallized from toluene. As a result, 31.7 g (0.073 mol, yield 69.4%) of an ocher solid was obtained.

Reference： [1]Current Patent Assignee: HODOGAYA CHEMICAL CO LTD - KR101553561, 2015, B1 Location in patent: Paragraph 0239-0243

78
[ 4165-57-5 ]
[ 572-83-8 ]
C₂₆H₉⁽²⁾H₁₀BrO₂ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Stage #1: bromobenzene-d5 With n-butyllithium In tetrahydrofuran at -78℃; for 1.5h; Stage #2: 2-bromoanthracene-9,10-dione In tetrahydrofuran at 20℃; for 24h; Stage #3: With hydrogenchloride In tetrahydrofuran; water	10.10-1 Synthesis Example 10- (1): Synthesis of 2-bromo-9,10-di(phenyl-d5)anthracene With stirring 500ml round bottom flaskBromobenzene disubstituted33.9 g (0.209 mol) and 100 ml of THF were added. After the temperature was dropped to -78 ° C, 9.1 ml (0.209 mol) of n-BuLi was slowly added dropwise.After the dropwise addition, the mixture was stirred for 1 hour and 30 minutes, and 20 g (0.070 mol) of 2-bromoanthraquinone was dissolved in 100 ml of THF and rapidly added.After standing for 10 minutes, the mixture was stirred at room temperature for 1 day. When the reaction ends,100 ml of 2N hydrochloric acid was added to make it acidic, and concentrated. 34.69 g (0.209 mol) of KI was added to the concentrated reaction mass in a 500 ml round bottom flask,NaH2PO2H2O was refluxed with 44.30 g (0.418 mol) and 200 ml of acetic acid for 3 hours.Upon completion of the reaction, the mixture was lowered to room temperature, and the resulting solid was filtered, washed with methanol, and recrystallized from toluene. As a result, 18.0 g (0.043 mol, yield 61.6%) of an ocher solid was obtained.

Reference： [1]Current Patent Assignee: HODOGAYA CHEMICAL CO LTD - KR101553561, 2015, B1 Location in patent: Paragraph 0265-0269

79
[ 1082549-89-0 ]
[ 572-83-8 ]
C₄₄H₂₆N₂O₂ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
60%	With tetrakis(triphenylphosphine) palladium(0); Aliquat 336; potassium carbonate; In water; toluene; at 100℃; for 24h;Inert atmosphere;	According to the reaction formula, compound 8 is prepared as follows:M7 (6.41 g, 12.00 mmol) and 2-bromoanthraquinone (3.44 g, 12 mmol) were added to a 300 mL pressure flask with a magnetic stir bar. Toluene (75 mL) and K2CO3 aqueous solution (2M, 25 mL H2O) were added and sparged with nitrogen, and then Aliquat 336 (0.2 mmol) and tetrakis(triphenylphosphine)palladium (0.46 g, 0.40 mmol) were added to the flask. The reaction was stirred at 100C for 24 hours, and then cooled to room temperature. The reaction was washed with water and ethyl acetate. The organic layer was dried over MgSO4, and the solvent was removed under vacuum. Purification by column chromatography gave compound 8 as a yellow product in 60% yield.

Reference： [1]Patent: CN111171010,2020,A .Location in patent: Paragraph 0100; 0101

80
[ 572-83-8 ]
[ 676578-20-4 ]

Reference： [1]Organic electronics,2020,vol. 85

81
[ 572-83-8 ]
C₂₅H₂₈BNO₂S [ No CAS ]
C₃₃H₂₃NO₂S [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
81%	With tetrakis(triphenylphosphine) palladium⁽⁰⁾; potassium carbonate In water; toluene at 80℃; for 24h; Inert atmosphere;	2.50g, 6mmol of the 9,9-dimethyl-10-(5-pinacol ester thiophen-2-yl)acridine, 1.44g, 5mmol of 2-bromoanthraquinone, 20mL of toluene and 10 mL of a 2.5 M potassium carbonate aqueous solution was added to a 100 mL Shrek bottle, and argon gas was used for pumping to obtain an eighth solution. 0.24g, 0.2mmol of tetratriphenylphosphine palladium was added to the eighth solution, and the reaction was refluxed at a temperature of 80°C for 24h to obtain a ninth solution. After cooling to room temperature, the ninth solution was extracted with dichloromethane, washed with water, dried, filtered and spin-dried to obtain a tenth solution;The tenth solution column was chromatographed with 200-300 mesh silica gel, and the post-interim eluent was petroleum ether/DCM to obtain 2.02 g of the target product with a yield of 81%.

Reference： [1]Current Patent Assignee: TCL TECHNOLOGY GROUP CORPORATION - CN111018726, 2020, A Location in patent: Paragraph 0040; 0050-0053

82
[ 78602-28-5 ]
[ 572-83-8 ]
C₄₂H₂₇Br [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
69%	Stage #1: 1-bromo-2-(2-phenylethenyl)benzene With n-butyllithium In tetrahydrofuran at -78℃; for 2h; Inert atmosphere; Stage #2: 2-bromoanthracene-9,10-dione In tetrahydrofuran at -78 - 20℃; for 6h; Inert atmosphere; Further stages;	5.1 Under a nitrogen atmosphere, the reactant 1-bromo-2-styrylbenzene (B) (6 mmol) was added to 100 mL of anhydrous THF, and stirred at -78°C for 10 min. After the reaction solution was cooled, 1.6M n-BuLi (6mmol) was added dropwise. After the addition was completed, the reaction was kept at -78 for 2h; 2-bromoanthraquinone (A) (3mmol) was dissolved in 50mL of anhydrous THF solution, and then added dropwise to the low-temperature reaction solution with a syringe After the dripping is over, the reaction is continued at low temperature for 1 hour, and then the temperature is raised to room temperature for 5 hours. After the reaction is over, add a small amount of water to quench, add water and dichloromethane for extraction, collect the organic phase and dry with anhydrous sodium sulfate, collect the filtrate by suction and spin off the solvent to obtain the crude product.The above crude product was added to 80 mL of acetic acid under nitrogen, stirred and heated, and reacted at 120° C. for 2 hours, then 5 mL of hydrochloric acid was added, and the reaction was heated at this temperature for 12 hours. After the reaction is over, cool and extract, collect the organic phase and spin off the solvent, and purify by column chromatography to obtain intermediate E4 (yield 69%).

Reference： [1]Current Patent Assignee: TIANMA MICROELECTRONICS CO., LTD. - CN111732494, 2020, A Location in patent: Paragraph 0137-0143

83
[ 78602-28-5 ]
[ 572-83-8 ]
C₂₈H₁₇BrO [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
63%	Stage #1: 1-bromo-2-(2-phenylethenyl)benzene With n-butyllithium In tetrahydrofuran at -78℃; for 2h; Inert atmosphere; Stage #2: 2-bromoanthracene-9,10-dione In tetrahydrofuran at -78 - 20℃; for 6h; Inert atmosphere; Further stages;	1.1 Under a nitrogen atmosphere, the reactant 1-bromo-2-styrylbenzene (B) (6 mmol) was added to 100 mL of dry THF (tetrahydrofuran), and stirred at -78°C for 10 min. After the reaction solution was cooled, 1.6M N-BuLi (6mmol) was added dropwise. When the addition is over, keep the reaction at -78 for 2h; dissolve 2-bromoanthraquinone (A) (6mmol) into 50mL anhydrous THF solution, and then add dropwise with a syringe In the low-temperature reaction solution, after the dropping is finished, the reaction is continued at low temperature for 1 hour, and then the temperature is raised to room temperature for 5 hours. After the reaction is over, add a small amount of water to quench, add water and dichloromethane for extraction, collect the organic phase and dry with anhydrous sodium sulfate, collect the filtrate by suction and spin off the solvent to obtain the crude product.The above crude product was added to 80 mL of acetic acid under nitrogen, stirred and heated, and reacted at 120° C. for 2 hours, then 5 mL of hydrochloric acid was added, and the reaction was heated at this temperature for 12 hours. After the reaction is complete, cool and extract, collect the organic phase and spin off the solvent, and purify by column chromatography to obtain Intermediate C (yield 63%).

Reference： [1]Current Patent Assignee: TIANMA MICROELECTRONICS CO., LTD. - CN111732494, 2020, A Location in patent: Paragraph 0088-0093

84
[ 572-83-8 ]
[ 15861-48-0 ]
C₂₆H₁₅BrOS [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
69%	Stage #1: 2-bromophenyl phenyl sulfide With n-butyllithium In tetrahydrofuran at -78℃; for 2h; Inert atmosphere; Stage #2: 2-bromoanthracene-9,10-dione In tetrahydrofuran at -78 - 20℃; for 7h; Inert atmosphere; Further stages;	6.1 Example 6: Synthesis of compound H-69 Under a nitrogen atmosphere, add the reactant re-2 (4 mmol) to 100 mL of anhydrous THF, stir at -78°C for 10 min, wait for the reaction solution to cool, add 1.6M n-BuLi (4 mmol) dropwise, and wait for it to be added. At the end, keep the reaction at -78 for 2h; dissolve re-7 (4mmol) into 50mL anhydrous THF solution, then add it dropwise to the low-temperature reaction solution with a syringe. When the addition is over, continue the reaction at low temperature for 1h, then heat up Reaction at room temperature for 6h. After the reaction is over, add a small amount of water to quench, add water and dichloromethane for extraction, collect the organic phase and dry with anhydrous sodium sulfate, collect the filtrate by suction and spin off the solvent to obtain a crude product.The above crude product was added to 80 mL of acetic acid under nitrogen, stirred and heated, and reacted at 120° C. for 2 hours, and then 5 mL of hydrochloric acid was added, and the reaction was continued to be heated for 12 hours. After the reaction is over, cooling and extraction are performed, the organic phase is collected and the solvent is removed by spinning off, and purified by column chromatography to obtain the intermediate compound M33 (yield 69%).

Reference： [1]Current Patent Assignee: TIANMA MICROELECTRONICS CO., LTD. - CN111718322, 2020, A Location in patent: Paragraph 0162-0166

85
[ 572-83-8 ]
[ 1421752-82-0 ]
C₄₄H₂₇BrN₂ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
90%	With n-butyllithium In tetrahydrofuran at -78 - 20℃; for 2h;	10 Dissolve HP-NP14-PY4 (1mmol, 284mg) in anhydrous tetrahydrofuran solution (10ml), add 1.6M butyllithium solution (1mmol, 0.63ml) dropwise at -78°C, and then add 2-bromoanthraquinone (0.5mmol , 144mg), warm to room temperature and stir for 2 hours, add water (20ml) and extract with dichloromethane (340ml), dry the organic phase with anhydrous magnesium sulfate, and concentrate to obtain a dark solid. The dark solid was dissolved in acetic acid (30ml), potassium iodide (3mmol, 500mg), sodium hypophosphite monohydrate (6mmol, 1.1g) were added, stirred at 120°C for 3 hours, and then cooled to room temperature, a solid precipitated. The filtered solid was washed with cold water (320ml) and dried to obtain a white solid HP-AN-NP14-PY4 (300mg, 90% yield).
90%	Stage #1: 2-bromoanthracene-9,10-dione; 4-(4-bromonaphthalen-1-yl)pyridine With n-butyllithium In tetrahydrofuran at 20℃; for 2h; Stage #2: With sodium hypophosphite monohydrate; acetic acid; potassium iodide In tetrahydrofuran at 120℃; for 3h;	10 Preparation of compound HP-AN-NP14-PY4 Dissolve HP-NP14-PY4 (1mmol, 284mg) in anhydrous tetrahydrofuran solution (10ml), add 1.6M butyllithium solution (1mmol, 0.63ml) dropwise at -78°C, and then add 2-bromoanthraquinone (0.5mmol , 144mg), warm to room temperature and stir for 2 hours, add water (20ml) and extract with dichloromethane (340ml), dry the organic phase with anhydrous magnesium sulfate, and concentrate to obtain a dark solid.The dark solid was dissolved in acetic acid (30ml), potassium iodide (3mmol, 500mg), sodium hypophosphite monohydrate (6mmol, 1.1g) were added, and stirred at 120°C for 3 hours, then cooled to room temperature, and a solid precipitated.The filtered solid was washed with cold water (320ml) and dried to obtain a white solid HP-AN-NP14-PY4 (300mg, 90% yield).

Reference： [1]Current Patent Assignee: SHANGHAI PHICHEM MATERIAL COMPANY LIMITED - CN104744347, 2021, B Location in patent: Paragraph 0122-0125
[2]Current Patent Assignee: SHANGHAI PHICHEM MATERIAL COMPANY LIMITED - CN104744346, 2021, B Location in patent: Paragraph 0132-0135

86
[ 572-83-8 ]
[ 106-54-7 ]
C₂₀H₁₁ClO₂S [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
91%	With copper(l) iodide; potassium carbonate In N,N-dimethyl-formamide at 85℃; for 12h;	2.1. Synthesis of 2-((4-chlorophenyl)thio)anthracene-9,10-dione (AQ-SCl) 2-bromoanthracene-9,10-dione (0.50 g, 1.75 mmol), 4-chlorothiophenol(0.31 g, 2.11 mmol) and K2CO3 (1.10 g, 7.48 mmol) were dissolvedin 50 mL of N,N-Dimethylformamide (DMF) solution. Thereaction mixture was stirred for 5 min under the nitrogen, and CuI (0.02g, 0.12 mmol) was added to the solution, then the reaction temperaturewas adjusted to 85 C. After heating and stirring at 85 C for 12 h, thereaction was stopped and filtrated. The filtrate was put into NaOH solutionand collect the precipitated yellow solid through vacuum filtration.After further purification by silica gel column chromatography[dichloromethane: petroleum ether (DCM:PE) = 1:1.5], 0.56 g (1.60mmol) bright yellow powder was obtained, yield: 91%. 1H NMR (400 MHz, DMSO-d6) 8.22-8.18 (m, 1H), 8.18-8.12 (m, 2H), 7.95-7.92 (m,2H), 7.80 (s, 1H), 7.76 (d, J = 8.5 Hz, 2H), 7.68 (dd, J = 8.3, 2.0 Hz, 1H),7.57 (d, J = 8.4 Hz, 2H). 13C NMR (101 MHz, DMSO-d6) 182.52,182.19, 145.90, 136.52, 135.21, 134.01, 133.71, 133.50, 133.29,132.77, 130.23, 128.45, 127.24, 124.46, 123.83. (Figs. S1-2, SupportingInformation).

Reference： [1]Hu, Yingyuan; Huang, Fei-xiang; Li, Hao-ze; Li, Yan-Qing; Tang, Jian-Xin; Wei, Huai-xin; Wu, Ping; Xie, Feng-ming; Zhao, Xin [Organic electronics, 2021, vol. 96]

87
[ 572-83-8 ]
[ 89343-06-6 ]
C₂₅H₂₈O₂Si [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
97%	With palladium diacetate; triethylamine; XPhos In water at 80℃; for 1h; Milling;

Reference： [1]Feng, Chi; Gao, Yunpeng; Ito, Hajime; Kubota, Koji; Seo, Tamae [Chemical Science, 2022, vol. 13, # 2, p. 430 - 438]

88
[ 572-83-8 ]
[ 108-91-8 ]
C₃₄H₂₅NO₄ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
80%	With bis(tri-tertiary-butylphosphine)palladium⁽⁰⁾; sodium tertiary butoxide In 5,5-dimethyl-1,3-cyclohexadiene for 12h; Reflux;	6.1 1) Preparation of compound 6-1 After dissolving 2-bromoanthracene-9,10-dione (10 g, 34 mmol) in 200 mL of xylene, cyclohexylamine (1.6 g, 15.7 mmol), sodium-t-butoxide ( 6.7 g, 70 mmol) was added, and 0.102 g (0.005 mol%)) of BTP (bis(trittbutylphosphine)palladium(0)) was added under reflux stirring, followed by stirring under reflux for 12 hours. After completion of the reaction, the solvent is removed by cooling to room temperature, filtration and then reduced pressure. Then, ethyl acetate and an excess of hexane were added to the concentrated compound, and the slurry was filtered to obtain compound 6-1 as a gray solid. (6.4 g, yield 80%)

Reference： [1]Current Patent Assignee: LG CHEM CO.,LTD. - KR2021/152729, 2021, A Location in patent: Paragraph 0213-0216

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