[ CAS No. 7025-06-1 ] {[proInfo.proName]}

Name: 7025-06-1|1-Bromo-2-phenoxybenzene|97%
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Quality Control of [ 7025-06-1 ]

COA NMR CNMR HPLC LC-MS

Related Doc. of [ 7025-06-1 ]

SDS Specification

Alternatived Products of [ 7025-06-1 ]

Product Details of [ 7025-06-1 ]

CAS No. :	7025-06-1	MDL No. :	MFCD00626462
Formula :	C₁₂H₉BrO	Boiling Point :	-
Linear Structure Formula :	-	InChI Key :	RRWFUWRLNIZICP-UHFFFAOYSA-N
M.W :	249.10	Pubchem ID :	37483
Synonyms :

Calculated chemistry of [ 7025-06-1 ] Expand+

Physicochemical Properties

Num. heavy atoms :	14
Num. arom. heavy atoms :	12
Fraction Csp3 :	0.0
Num. rotatable bonds :	2
Num. H-bond acceptors :	1.0
Num. H-bond donors :	0.0
Molar Refractivity :	60.66
TPSA :	9.23 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) :	-5.1 cm/s

Lipophilicity

Log Po/w (iLOGP) :	2.83
Log Po/w (XLOGP3) :	3.83
Log Po/w (WLOGP) :	4.24
Log Po/w (MLOGP) :	4.01
Log Po/w (SILICOS-IT) :	3.73
Consensus Log Po/w :	3.73

Druglikeness

Lipinski :	0.0
Ghose :	None
Veber :	0.0
Egan :	0.0
Muegge :	1.0
Bioavailability Score :	0.55

Water Solubility

Log S (ESOL) :	-4.3
Solubility :	0.0125 mg/ml ; 0.0000502 mol/l
Class :	Moderately soluble
Log S (Ali) :	-3.72
Solubility :	0.0475 mg/ml ; 0.000191 mol/l
Class :	Soluble
Log S (SILICOS-IT) :	-5.51
Solubility :	0.000766 mg/ml ; 0.00000308 mol/l
Class :	Moderately soluble

Medicinal Chemistry

PAINS :	0.0 alert
Brenk :	0.0 alert
Leadlikeness :	2.0
Synthetic accessibility :	1.76

Safety of [ 7025-06-1 ]

Signal Word:	Warning	Class:	N/A
Precautionary Statements:	P280-P305+P351+P338	UN#:	N/A
Hazard Statements:	H302	Packing Group:	N/A
GHS Pictogram:

Application In Synthesis of [ 7025-06-1 ]

* 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 [ 7025-06-1 ]
Downstream synthetic route of [ 7025-06-1 ]

[ 7025-06-1 ] Synthesis Path-Upstream 1~12

1
[ 95-56-7 ]
[ 98-80-6 ]
[ 7025-06-1 ]

Yield	Reaction Conditions	Operation in experiment
47%	With copper diacetate; triethylamine In dichloromethane at 20℃; for 18 h; Molecular sieve	A mixture of 2-bromophenol (0.211 ml, 2 mmol), phenylboronic acid (490 mg, 4 mmol), copper acetate (364 mg, 2 mmol), TEA (1.38 ml, 10 mmol) and 4A molecular sieves in DCM (25 ml) was stirred at r.t. for 18 h. The slurry was filtered through celite and concentrated in vacuo. This was then diluted with EtOAc and NaHCO₃ solution, extracted and the organic portions were washed with brine and dried (MgSO₄). The crude mixture was purified by flash chromatography (hexane) to yield the desired product as a colourless oil, 232 mg, 47 percent yield. R.f. 0.75 (DCM),LCMS: U = 1.3 min (95 percent MeOH in water), m/z M-H 246.84, 248.86,HPLC: U= 2.88 min (90 percent ACN in water), 98percent,¹H NMR (CDCl₃, 270 MHz,): δ 6.95-7.04 (4H, m, ArH), 7.11 (IH, td, J=Ll, 8.0 Hz,ArH), 7.22-7.37 (3H, m, ArH), 7.61-7.65 (IH, m, ArH), 1³C NMR (CDCl₃, 68 MHz): 115.0 (ArC), 118.2, 120.7, 123.5, 125.1, 128.8, 129.9, 133.9(ArCH), 153.8, 156.9 (ArC).
15.1%	With pyridine; copper diacetate In dichloromethane at 20℃; for 18 h; Molecular sieve	1-Bromo-2-phenoxybenzene 2-Bromophenol (1.22 mL, 11.6 mmol), phenylboronic acid (2.8 g, 23.1 mmol), Cu(OAc)₂ (4.2 g, 23.1 mmol) and pyridine (4.66 mL, 57.8 mmol) were dissolved in dichloromethane (100 mL) in a reaction vessel holding 1 g of 4 Å M.S. and stirred at room temperature for 18 hours. After the reaction was completed, the reaction mixture was diluted with dichloromethane and filtered through Celite. The filtrate was extracted with 1 N NaOH and brine, and the organic layer was dried with anhydrous MgSO₄ and filtered again. The filtrate was concentrated under reduced pressure) to obtain 436 mg of the target compound (1.75 mmol, 15.1percent). ¹H NMR (300 MHz, CDCl₃) δ 7.63 (dd, J=8.1 Hz, J=1.8 Hz, 1H), 7.36-7.23 (m, 3H), 7.13-7.08 (m, 1H), 7.04-6.94 (m, 4H).
612 mg	With copper diacetate; triethylamine In dichloromethane at 20℃; for 16 h; Molecular sieve	To a solution of 2-bromophenol (1 g, 5.84 mmol), phenylboronic acid (1.42 g, 11.69 mmol) and TEA (2.95 g, 29.2 mmol) in DCM (30 mL) was added Cu(OAc)₂ (1.05 g, 5.84 mmol) and 4A molecular sieves (500 mg). The reaction mixture was stirred at room temperature over air with a dry tube attached for 16h. The mixture was filtered and the filtrate was washed by water (50 mL) and brine (30 mL). The organic layer was dried over anhydrous Na₂S0₄, filtered and concentrated with the residue purified by column chromatography to give 612 mg of the desired product.

Reference： [1] Patent: WO2009/66072, 2009, A2, . Location in patent: Page/Page column 99
[2] Patent: US2014/228568, 2014, A1, . Location in patent: Paragraph 0162-0163
[3] Journal of Medicinal Chemistry, 2004, vol. 47, # 3, p. 744 - 755
[4] Patent: WO2014/100695, 2014, A1, . Location in patent: Paragraph 00386

2
[ 2688-84-8 ]
[ 7025-06-1 ]

Yield	Reaction Conditions	Operation in experiment
45%	Stage #1: With hydrogen bromide; sodium nitrite In water at 0℃; for 0.166667 h; Stage #2: With copper(I) bromide In water for 0.5 h; Heating / reflux	A solution of sodium nitrite (9.2 g, 0.135 mol) in water (20 ml) was added dropwise to a solution of 2-phenoxyaniline (25 g, 0.135 mol) in 40percent hydrobromic acid (50 ml) at 0° C. and stirred for another 10 minutes. Then the reaction mixture was added to the boiling mixture of cuprous bromide (21.3 g, 0.149 mol) in 40percent hydrobromic acid (50 ml) and after addition it was allowed to reflux for another 30 minutes. Reaction mixture was cooled, diluted with water and extracted with diethyl ether. The diethyl ether layer was washed with 5percent hydrochloric acid, 10percent potassium hydroxide, water, brine, dried over sodium sulfate and concentrated to give the crude intermediate. The sub.-title compound (14.8 g, 45percent) was obtained by column purification of the crude intermediate using pet ether as eluent

Reference： [1] Patent: US2008/15237, 2008, A1, . Location in patent: Page/Page column 34
[2] Journal of Organic Chemistry, 1960, vol. 25, p. 1590 - 1595
[3] Organometallics, 2017, vol. 36, # 12, p. 2338 - 2344

3
[ 108-86-1 ]
[ 95-56-7 ]
[ 7025-06-1 ]

Yield	Reaction Conditions	Operation in experiment
62%	With potassium <i>tert</i>-butylate In dimethyl sulfoxide at 40 - 45℃;	General procedure: Phenol (94mg, 1mmol) and bromobenzene (314mg, 2.0mmol) were added to a single necked flask containing DMSO (1mL) and resulted reaction mixture was stirred for 5min. After this potassium tert-butoxide (280mg, 2.5mmol) was added portion wise and stirring continued for 6–8h at 40–45°C. The progress of reaction was monitored by TLC. Upon completion of the reaction, mixture poured into water, and extracted four times with 20mL of ethyl acetate. The combined organic layer was dried over Na₂SO₄, and filtered. The solvent was removed in vacuo and the residue was purified by column chromatography (silica gel, eluent: hexane/ethyl acetate) to afford the coupling product.

Reference： [1] Tetrahedron, 2013, vol. 69, # 26, p. 5383 - 5392

4
[ 7732-18-5 ]
[ 108-95-2 ]
[ 583-53-9 ]
[ 7025-06-1 ]

Yield	Reaction Conditions	Operation in experiment
46%	With pyridine; hydrogenchloride; sodium methylate In dichloromethane; benzene	a) 1-Bromo-2-phenoxybenzene. This compound was prepared according to the procedure described by Williams.¹² Phenol (9.4 g, 100 mmol) was added to a suspension of NaOMe (5.3 g, 98 mmol) in anhydrous benzene (100 mL), and the resulting solution was distilled to dryness. The residue was cooled, anhydrous pyridine (150 mL) was added, and the solution heated to reflux under N₂. Dibromobenzene (50 g, 210 mmol) was then added, followed by CuCl (1.5 g), and the mixture was refluxed for 2 days. After cooling, the reaction mixture was partitioned between H₂ O (100 mL) and Et₂ O (200 mL). The organic extract was acidified with conc. HCl in ice, and was further rinsed with 1N HCl (100 mL), H₂ O (2*100 mL) and brine (100 mL). The organic extract was dried over Na₂ SO₄, and the solvent removed in vacuo. The residue was taken up in CH₂ Cl₂ and filtered through silica gel, and the solvent was removed from the filtrate in vacuo. Distillation of the residue via a Kugelrohr apparatus gave product as a colorless oil (11.5 g, 46percent yield):¹⁹ ¹ H NMR (CDCl₃) δ7.62 (d, 1H, J=7.8 Hz), 7.30 (t, 2H, J=8.4 Hz), 7.24 (t, 1H, J=7.5 Hz), 7.10 (t, 1H, J=7.2 Hz), 7.02 (d, 1H, J=7.8 Hz), 6.96 (m, 3H); ¹³ C NMR (CDCl₃) δ156.9, 153.7, 133.8, 129.8, 128.7, 125.0, 123.4, 120.6, 118.1, 114.9. Anal. Calcd. for C₁₂ H₉ BrO.0.4 H₂ O: C, 56.23; H, 3.85. Found: C, 56.11; H, 3.54.

Reference： [1] Patent: US5668151, 1997, A,

5
[ 95-56-7 ]
[ 639-58-7 ]
[ 7025-06-1 ]

Yield	Reaction Conditions	Operation in experiment
60%	at 20℃; for 30 h;	General procedure: To a flask containing a stirring mixture of triphenyltin chloride (0.5 mmol, 0.193 g) and phenol (1 mmol, 0.094 g) in triethylamine (10 equiv, 1.4 mL) at room temperature, copper acetate (40 molpercent, 0.076 g) was added. Monitoring the reaction with TLC showed that the reaction was completed within 30 h. The reaction mixture was washed with HCl (1 N, 1 mL) to remove the excess of Et₃N. Then, the catalyst was filtered and the aqueous solution was extracted with ethyl acetate (5×10 mL) and dried over anhydrous Na₂SO₄. The solvent was evaporated and column chromatography of the crude mixture on silica-gel using n-hexane/ethyl acetate (3/1) as eluent afforded biphenyl ether in 85percent yield (0.130 g).

Reference： [1] Journal of Organometallic Chemistry, 2013, vol. 740, p. 123 - 130

6
[ 583-55-1 ]
[ 108-95-2 ]
[ 7025-06-1 ]

Yield	Reaction Conditions	Operation in experiment
50%	With sodium hydride In tetrahydrofuran	take 0.01 mol of benzoic acid and dissolve in 100 mL of anhydrous tetrahydrofenamic acid. Stir and accurately weigh 0.4 mol of sodium hydrideAdd to the reaction bottle, do not be too fast to prevent too much bubble, add the solution after the yellow, then add 1-bromo-2-iodobenzeneThe reaction product was filtered to remove the solid material. The filtrate was dried and dissolved in dichloromethane. The column was washed with petroleum ether: ethyl acetate = 1: 5 (volume ratio), and the reaction mixture was stirred at room temperature. Column to give 1-bromo-2-phenoxybenzene (intermediateBody A-l) (0.05 mol, y = 50percent). Mass spectrum: 249.97
36%	Stage #1: at 50℃; for 0.5 h; Stage #2: at 100 - 150℃;	phenol (18.5 mg, 1.97 mmol) and KOH (110 mg, 1.97 mmol) were stirred at 50 °C for 30 mm before the addition of 1-bromo-2-iodobenzene (557 mg, 1.97 mmol) and Cu powder (125 mg, 1.97 mmol). The reaction mixture was heated to 150 °C for 2 hrs and then 100 °C overnight. Crude material was purified by FC on silica gel (eluent: cyclohexane), affording 1-bromo-2-phenoxybenzene (p8, 179 mg, y= 36percent) asan oil.1H NMR (CHLOROFORM-d): 6 ppm 7.86 - 7.93 (m, 1 H) 7.33 - 7.42 (m, 3 H) 7.15 (t, 1 H) 7.01 (d, 2 H)6.87 - 6.96 (m, 2 H)

Reference： [1] Patent: CN106565434, 2017, A, . Location in patent: Paragraph 0119-0121
[2] Patent: WO2016/42452, 2016, A1, . Location in patent: Page/Page column 80

7
[ 108-95-2 ]
[ 583-53-9 ]
[ 7025-06-1 ]

Yield	Reaction Conditions	Operation in experiment
45%	at 180℃;	1,2- dibromobenzenes (451.1 g, 1.9 mol), phenols(150.0 g, 1.50 mol), and potassium carbonates (132.2 g, 956 mmol) and copper(I) oxides (273.7 g, 1.9 mol) are mixed and the glass bead is added. Thereaction mixture is stirred in all night long in the inner temperature of 180.The arrangement (batch) is lifted after doing the cooling to DCM of 300 ml. Inthe Buechner funnel and after the arrangement solution, it filters through theCelite.The filtered material is evaporated in the Rotavapor. Oil is distilled from(1.5 mbar, and the head temperature 135)under the HI-vacuum. The white solid of 168.1 g is isolated (45percent of theTheoretical value)

Reference： [1] Patent: KR2015/142006, 2015, A, . Location in patent: Paragraph 0149; 0153; 0154

8
[ 958244-59-2 ]
[ 7025-06-1 ]

Reference： [1] European Journal of Inorganic Chemistry, 2013, # 34, p. 5911 - 5918

9
[ 95-56-7 ]
[ 66003-76-7 ]
[ 7025-06-1 ]

Reference： [1] Organic Letters, 2011, vol. 13, # 20, p. 5628 - 5631

10
[ 95-56-7 ]
[ 1483-73-4 ]
[ 7025-06-1 ]

Reference： [1] Environmental Science and Technology, 1999, vol. 33, # 17, p. 3033 - 3037

11
[ 150-46-9 ]
[ 7025-06-1 ]
[ 51067-38-0 ]

Reference： [1] Patent: US6197770, 2001, B1,

12
[ 5419-55-6 ]
[ 7025-06-1 ]
[ 108238-09-1 ]

Yield	Reaction Conditions	Operation in experiment
80%	Stage #1: With n-butyllithium In tetrahydrofuran at -78℃; for 3 h; Inert atmosphere Stage #2: at -78℃; for 2 h; Inert atmosphere	The 1-bromo-2-phenoxybenzene 0.018 µM is dissolved in 100 ml, in dry THF, added after the never-dried 500 ml three-mouth bottle, N₂-78 °C under the protection of the reaction 30min, slow adds by drops positively BuLi 0.027 µM, after dropping maintain -78 °C reaction 3h, then slowly dropping triisopropyl borate 0.02 µM, after dropping the reaction is maintained in the -78 °C reaction 2h, slow heating to room temperature, the reaction overnight, TLC monitoring after the reaction is completed, water slow quenching the reaction solution, extraction to dryness, to obtain 2-phenoxyphenylboronic acid (B-1) 0.0144 µM, and the yield is 80percent. Mass spectrum: 214.06.

Reference： [1] Patent: CN106565434, 2017, A, . Location in patent: Paragraph 0128-0131

[ 7025-06-1 ] Synthesis Path-Downstream 1~109

1
[ 7025-06-1 ]
[ 132-64-9 ]

Reference： [1]Synthesis,1983,p. 234 - 235

2
[ 7025-06-1 ]
[ 13107-20-5 ]

Reference： [1]Tetrahedron Letters,1986,vol. 27,p. 2247 - 2250

3
[ 2417-10-9 ]
[ 7025-06-1 ]
[ 104096-16-4 ]

Reference： [1]Journal of Organic Chemistry,1960,vol. 25,p. 1590 - 1595

4
[ 2688-84-8 ]
[ 7025-06-1 ]

Yield	Reaction Conditions	Operation in experiment
45%		A solution of sodium nitrite (9.2 g, 0.135 mol) in water (20 ml) was added dropwise to a solution of 2-phenoxyaniline (25 g, 0.135 mol) in 40percent hydrobromic acid (50 ml) at 0° C. and stirred for another 10 minutes. Then the reaction mixture was added to the boiling mixture of cuprous bromide (21.3 g, 0.149 mol) in 40percent hydrobromic acid (50 ml) and after addition it was allowed to reflux for another 30 minutes. Reaction mixture was cooled, diluted with water and extracted with diethyl ether. The diethyl ether layer was washed with 5percent hydrochloric acid, 10percent potassium hydroxide, water, brine, dried over sodium sulfate and concentrated to give the crude intermediate. The sub.-title compound (14.8 g, 45percent) was obtained by column purification of the crude intermediate using pet ether as eluent

Reference： [1]Patent: US2008/15237,2008,A1 .Location in patent: Page/Page column 34
[2]Journal of Organic Chemistry,1960,vol. 25,p. 1590 - 1595
[3]Organometallics,2017,vol. 36,p. 2338 - 2344

5
[ 7025-06-1 ]
[ 163041-47-2 ]
(E)-3-Methoxy-2-(2-phenoxy-phenyl)-acrylic acid methyl ester [ No CAS ]

Reference： [1]Tetrahedron,1998,vol. 54,p. 7595 - 7614

6
[ 7025-06-1 ]
3-{1-(4-chloro-benzyl)-2-oxo-2-[4-(2-phenoxy-phenyl)-piperazin-1-yl]-ethylcarbamoyl}-3,4-dihydro-1H-isoquinoline-2-carboxylic acid tert-butyl ester [ No CAS ]

Reference： [1]Journal of Medicinal Chemistry,2004,vol. 47,p. 744 - 755

7
[ 7025-06-1 ]
(R)-1,2,3,4-Tetrahydro-isoquinoline-3-carboxylic acid {(R)-1-(4-chloro-benzyl)-2-oxo-2-[4-(2-phenoxy-phenyl)-piperazin-1-yl]-ethyl}-amide; compound with trifluoro-acetic acid [ No CAS ]

Reference： [1]Journal of Medicinal Chemistry,2004,vol. 47,p. 744 - 755

8
[ 71-43-2 ]
tin tetrachloride [ No CAS ]
[ 7025-06-1 ]

Reference： [1]Environmental science and technology,1999,vol. 33,p. 3033 - 3037

9
[ 3612-20-2 ]
[ 7025-06-1 ]
[ 7732-18-5 ]
[ 186185-96-6 ]

Yield	Reaction Conditions	Operation in experiment
71%	With n-butyllithium; In tetrahydrofuran; pentane;	b) 4-(2-Phenoxyphenyl)-1-(phenylmethyl)-4-piperidinol. To a stirred solution of the <strong>[7025-06-1]1-<strong>[7025-06-1]bromo-2-phenoxybenzene</strong></strong> (3.0 g, 12 mmol) in anhydrous THF (20 mL) at -78° C. under N2 was slowly added n-butyllithium (2.0M in pentane, 6.0 mL, 12 mmol). The resulting solution was stirred for 30 min, followed by the dropwise addition of 1-benzyl-4-piperidinone (1.9 g, 10 mmol) in anhydrous THF (10 mL). The mixture was stirred for 1 hr at -78° C., and then quenched with saturated NH4 Cl. Sufficient H2 O was added to dissolve any solids, the layers separated, and the aqueous extract discarded. The organic extract was dried over Na2 SO4, and the solvent removed in vacuo. Flash chromatography of the residue (SiO2: MeOH/CH2 Cl2), afforded a viscous, light yellow oil (2.46 g, 71percent yield): 1 H NMR (CDCl3) delta7.33 (m, 11H), 7.03 (d, 2H, J=7.5 Hz), 6.76 (d, 1H, J=8.1 Hz), 3.56 (s, 2H), 3.52 (s, 1H), 2.75 (m, 2H), 2.56 (t, 2H, J=11.7 Hz), 2.22 (t, 2H, J=12.6 Hz), 2.04 (m, 2H); 13 C NMR (CDCl3) delta156.2, 155.8, 138.6, 137.4, 130.0, 129.3, 128.3, 128.2, 126.9, 126.2, 124.1, 123.3, 119.7, 118.7, 71.1, 63.2, 49.2, 36.4. Anal. Calcd. for C24 H25 NO2.0.7 H2 O: C, 77.47; H, 7.15; N, 3.77. Found: C, 77.35; H, 6.90; N, 4.13.

Reference： [1]Patent: US5668151,1997,A

10
[ 7732-18-5 ]
[ 108-95-2 ]
[ 583-53-9 ]
[ 7025-06-1 ]

Yield	Reaction Conditions	Operation in experiment
46%	With pyridine; hydrogenchloride; sodium methylate;copper(l) chloride; In dichloromethane; benzene;	a) 1-Bromo-2-phenoxybenzene. This compound was prepared according to the procedure described by Williams.12 Phenol (9.4 g, 100 mmol) was added to a suspension of NaOMe (5.3 g, 98 mmol) in anhydrous benzene (100 mL), and the resulting solution was distilled to dryness. The residue was cooled, anhydrous pyridine (150 mL) was added, and the solution heated to reflux under N2. Dibromobenzene (50 g, 210 mmol) was then added, followed by CuCl (1.5 g), and the mixture was refluxed for 2 days. After cooling, the reaction mixture was partitioned between H2 O (100 mL) and Et2 O (200 mL). The organic extract was acidified with conc. HCl in ice, and was further rinsed with 1N HCl (100 mL), H2 O (2*100 mL) and brine (100 mL). The organic extract was dried over Na2 SO4, and the solvent removed in vacuo. The residue was taken up in CH2 Cl2 and filtered through silica gel, and the solvent was removed from the filtrate in vacuo. Distillation of the residue via a Kugelrohr apparatus gave product as a colorless oil (11.5 g, 46percent yield):19 1 H NMR (CDCl3) delta7.62 (d, 1H, J=7.8 Hz), 7.30 (t, 2H, J=8.4 Hz), 7.24 (t, 1H, J=7.5 Hz), 7.10 (t, 1H, J=7.2 Hz), 7.02 (d, 1H, J=7.8 Hz), 6.96 (m, 3H); 13 C NMR (CDCl3) delta156.9, 153.7, 133.8, 129.8, 128.7, 125.0, 123.4, 120.6, 118.1, 114.9. Anal. Calcd. for C12 H9 BrO.0.4 H2 O: C, 56.23; H, 3.85. Found: C, 56.11; H, 3.54.

Reference： [1]Patent: US5668151,1997,A

11
[ 150-46-9 ]
[ 7025-06-1 ]
[ 51067-38-0 ]

Yield	Reaction Conditions	Operation in experiment
	With ammonium chloride; iodine; In tetrahydrofuran;	a. 4-Phenyloxyphenyl boronic acid Mg turnings (820 mg, 34.2 mmol) are suspended in THF (60 mL) in a three-necked flask fitted with addition funnel and condenser. A crystal of iodine is added to the suspension. Phenyloxy phenyl bromide (5 mL, 28.5 mmol) in THF (15 mL) is added dropwise using the addition funnel to the Mg/I2 suspension, maintaining a slow reflux of the solvent, then after the completion of addition the mixture is brought to reflux for the next 3 hrs. After allowing the mixture to cool down to room temperature, triethyl borate (5.8 mL, 34.20 mmol) in THF (15 mL) is added dropwise via the addition funnel. To the mixture is added 10percent ammonium chloride (50 mL), the layers are separated and the aqueous layer is extracted with EtOAc (50 mL). The combined organic extracts are dried over MgSO4, filtered and the solvents removed by rotary evaporation. The crude solid product is recrystallized from EtOAc/hexanes mixtures to afford an off-white boronic acid product, which is stored under refrigeration.

Reference： [1]Patent: US6197770,2001,B1

12
[ 95-56-7 ]
[ 66003-76-7 ]
[ 7025-06-1 ]

Reference： [1]Organic Letters,2011,vol. 13,p. 5628 - 5631

13
[ 108-86-1 ]
[ 95-56-7 ]
[ 7025-06-1 ]

Yield	Reaction Conditions	Operation in experiment
62%	With potassium tert-butylate; In dimethyl sulfoxide; at 40 - 45℃;	General procedure: Phenol (94mg, 1mmol) and bromobenzene (314mg, 2.0mmol) were added to a single necked flask containing DMSO (1mL) and resulted reaction mixture was stirred for 5min. After this potassium tert-butoxide (280mg, 2.5mmol) was added portion wise and stirring continued for 6?8h at 40?45°C. The progress of reaction was monitored by TLC. Upon completion of the reaction, mixture poured into water, and extracted four times with 20mL of ethyl acetate. The combined organic layer was dried over Na2SO4, and filtered. The solvent was removed in vacuo and the residue was purified by column chromatography (silica gel, eluent: hexane/ethyl acetate) to afford the coupling product.

Reference： [1]Tetrahedron,2013,vol. 69,p. 5383 - 5392

14
[ 95-56-7 ]
[ 639-58-7 ]
[ 7025-06-1 ]

Yield	Reaction Conditions	Operation in experiment
60%	With copper diacetate; triethylamine; at 20℃; for 30h;	General procedure: To a flask containing a stirring mixture of triphenyltin chloride (0.5 mmol, 0.193 g) and phenol (1 mmol, 0.094 g) in triethylamine (10 equiv, 1.4 mL) at room temperature, copper acetate (40 molpercent, 0.076 g) was added. Monitoring the reaction with TLC showed that the reaction was completed within 30 h. The reaction mixture was washed with HCl (1 N, 1 mL) to remove the excess of Et3N. Then, the catalyst was filtered and the aqueous solution was extracted with ethyl acetate (5×10 mL) and dried over anhydrous Na2SO4. The solvent was evaporated and column chromatography of the crude mixture on silica-gel using n-hexane/ethyl acetate (3/1) as eluent afforded biphenyl ether in 85percent yield (0.130 g).

Reference： [1]Journal of Organometallic Chemistry,2013,vol. 740,p. 123 - 130

15
[ 958244-59-2 ]
[ 7025-06-1 ]

Reference： [1]European Journal of Inorganic Chemistry,2013,p. 5911 - 5918

16
[ 7025-06-1 ]
[ 1079-66-9 ]
[ 183383-68-8 ]

Reference： [1]European Journal of Inorganic Chemistry,2013,p. 5911 - 5918

17
[ 64-18-6 ]
[ 7025-06-1 ]
[ 1616099-47-8 ]
[ 1616098-97-5 ]

Yield	Reaction Conditions	Operation in experiment
15%		A mixture of l-(3,4-dihydroisoquinolin-2(lH)-yl)-3-(3-(4,4,5,5-tetramethyl-l,3,2- dioxaborolan-2-yl)phenoxy)propan-2-ol (200 mg, 0.489 mmol), l-<strong>[7025-06-1]bromo-2-phenoxybenzene</strong> (120 mg, 0.489 mmol), Pd(dppf)Cl2 (36 mg, 0.049 mmol), K2C03 (202 mg, 1.47 mmol) in H20-dioxane (1 mL/ 3 mL) was stirred at 100°C under microwave heating for 15 min. The solvent was removed and the crude product purified by prep-HPLC to afford the title compound as the formate salt (33 mg, 15percent). 1H NMR (400 MHz, MeOD): delta 8.46 (s, 1H), 7.49 -7.22 (m, 9H), 7.17-7.11 (m, 3H), 7.04 - 6.98 (m, 2H), 6.92 - 6.90 (m, 1H), 6.87- 6.84 (m, 1H), 4.43- 4.37 (m, 1H), 4.28 (s, 2H), 3.98 (d, J = 5.2 Hz, 2H), 3.41 (t, J = 6.4 Hz, 2H), 3.25-3.13 (m, 4H)ppm; ESI-MS (m/z): 452.3 [M+l] +.

Reference： [1]Patent: WO2014/100695,2014,A1 .Location in patent: Paragraph 00387

18
[ 7025-06-1 ]
2-(1-(2-phenoxyphenyl)-2-oxabicyclo[2.2.2]octan-4-yl)acetonitrile [ No CAS ]

Reference： [1]Patent: US2014/275173,2014,A1

19
[ 7025-06-1 ]
2-(1-(2-phenoxyphenyl)-2-oxabicyclo[2.2.2]octan-4-yl)acetaldehyde [ No CAS ]

Reference： [1]Patent: US2014/275173,2014,A1

20
[ 7025-06-1 ]
2-(1-(2-phenoxyphenyl)-2-oxabicyclo[2.2.2]octan-4-yl)ethanol [ No CAS ]

Reference： [1]Patent: US2014/275173,2014,A1

21
[ 340022-81-3 ]
[ 7025-06-1 ]
(1-(2-phenoxyphenyl)-2-oxabicyclo[2.2.2]octan-4-yl)methyl 4-methylbenzenesulfonate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
44%		37A. (1-(2-Phenoxyphenyl)-2-oxabicyclo[2.2.2]octan-4-yl)methyl 4-methylbenzenesulfonate To a -78° C. solution of <strong>[7025-06-1]1-<strong>[7025-06-1]bromo-2-phenoxybenzene</strong></strong> (283 mg, 1.136 mmol) in anhydrous THF (5 mL) was added dropwise n-BuLi (545 muL of a 2.5 M solution in hexane, 1.363 mmol). The reaction was stirred at -78° C. for 0.5 h, after which a solution of 4-oxocyclohexane-1,1-diyl)bis(methylene)bis(4-methylbenzenesulfonate (1E; 530 mg, 1.14 mmol) in THF (4 mL) was added dropwise. The reaction mixture was slowly warmed to rt and stirred at rt for 2 h. Analytical HPLC showed the reaction was complete. Powdered NaOH (91 mg, 2.27 mmol) was added and the mixture was stirred under reflux for 18 h. The reaction was cooled to rt, diluted with water and extracted with EtOAc (2*). The organic layer was dried (MgSO4) and concentrated in vacuo. The crude oil purified by flash chromatography (SiO2) using a gradient from 0percent to 40percent EtOAc/hexane (15 min) to give the title compound (230 mg, 0.495 mmol, 44percent yield) as a white solid. LCMS [M+H]+=465.1; 1H NMR (CDCl3) delta: 7.85-7.77 (m, 2H), 7.76-7.69 (dd, J=7.9, 1.9 Hz, 1H), 7.41-7.30 (m, 4H), 7.20-7.14 (td, J=7.6, 1.9 Hz, 1H), 7.14-7.06 (m, 2H), 6.98-6.92 (dd, J=7.6, 1.5 Hz, 2H), 6.83-6.76 (dd, J=8.1, 1.4 Hz, 1H), 3.87 (s, 2H), 3.75 (s, 2H), 2.59-2.50 (ddd, J=13.5, 11.3, 4.1 Hz, 2H), 2.48 (s, 3H), 1.98-1.87 (m, 2H), 1.75-1.64 (td, J=11.3, 10.8, 2.7 Hz, 2H), 1.60-1.51 (m, 2H).

Reference： [1]Patent: US2014/275173,2014,A1 .Location in patent: Paragraph 0475; 0476

22
[ 583-55-1 ]
[ 108-95-2 ]
[ 7025-06-1 ]

Yield	Reaction Conditions	Operation in experiment
50%	With sodium hydride; In tetrahydrofuran;	take 0.01 mol of benzoic acid and dissolve in 100 mL of anhydrous tetrahydrofenamic acid. Stir and accurately weigh 0.4 mol of sodium hydrideAdd to the reaction bottle, do not be too fast to prevent too much bubble, add the solution after the yellow, then add 1-bromo-2-iodobenzeneThe reaction product was filtered to remove the solid material. The filtrate was dried and dissolved in dichloromethane. The column was washed with petroleum ether: ethyl acetate = 1: 5 (volume ratio), and the reaction mixture was stirred at room temperature. Column to give 1-bromo-2-phenoxybenzene (intermediateBody A-l) (0.05 mol, y = 50percent). Mass spectrum: 249.97
36%		phenol (18.5 mg, 1.97 mmol) and KOH (110 mg, 1.97 mmol) were stirred at 50 °C for 30 mm before the addition of 1-bromo-2-iodobenzene (557 mg, 1.97 mmol) and Cu powder (125 mg, 1.97 mmol). The reaction mixture was heated to 150 °C for 2 hrs and then 100 °C overnight. Crude material was purified by FC on silica gel (eluent: cyclohexane), affording 1-bromo-2-phenoxybenzene (p8, 179 mg, y= 36percent) asan oil.1H NMR (CHLOROFORM-d): 6 ppm 7.86 - 7.93 (m, 1 H) 7.33 - 7.42 (m, 3 H) 7.15 (t, 1 H) 7.01 (d, 2 H)6.87 - 6.96 (m, 2 H)

Reference： [1]Patent: CN106565434,2017,A .Location in patent: Paragraph 0119-0121
[2]Patent: WO2016/42452,2016,A1 .Location in patent: Page/Page column 80

23
[ 25032-74-0 ]
[ 7025-06-1 ]
9,9-bis(3-bromophenyl)-9H-xanthene [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
62%		First, magnesiums (3.17 g, 120.6 mmol) areintroduced to the flask including one iodine crystal. First, 1- bromo -2-phenoxy benzenes (23.2 g, 93.2 mmol), the anhydrous tetrahydrofuran of 190 ml,and 1,2- dimethoxyethane of 26 ml and 1,2- dichloroethane of 0.78 ml areintroduced to the dropping funnel. The outbound - material blend is dipped asthe gradually. In 70 the reactant, it cools for the additional 3 hoursafter doing the mixing. Bis (3- bromophenyl) methanones (32 g, 93.2 mmol) aredissolved among THF of 200 ml and it dips as the gradually. The reactant isstirred under the reflux for 4 hours. Subsequently, the arrangement is filteredand THF is removed of the Rotavapor. The acetic acid of 400 ml and concentratedhydrochloric acid of 75 ml are added and the water of 200 ml the mixture isadded in 75for 4 hours after doing the mixing. The solid in which the colour is pale isfiltered to the suction and it washes to the methanol. Solid is stirred for1 hour among the boiling ethyl acetate and it filters and it washes to ethanol.The yield is 28.2 g (62percent of the Theoretical value) as the white solid

Reference： [1]Patent: KR2015/142006,2015,A .Location in patent: Paragraph 0149; 0155; 0156

24
[ 25032-74-0 ]
[ 7025-06-1 ]
C₅₇H₄₂N₂O [ No CAS ]

Reference： [1]Patent: KR2015/142006,2015,A

25
[ 108-95-2 ]
[ 583-53-9 ]
[ 7025-06-1 ]

Yield	Reaction Conditions	Operation in experiment
45%	With copper(I) oxide; potassium carbonate; at 180℃;	1,2- dibromobenzenes (451.1 g, 1.9 mol), phenols(150.0 g, 1.50 mol), and potassium carbonates (132.2 g, 956 mmol) and copper(I) oxides (273.7 g, 1.9 mol) are mixed and the glass bead is added. Thereaction mixture is stirred in all night long in the inner temperature of 180.The arrangement (batch) is lifted after doing the cooling to DCM of 300 ml. Inthe Buechner funnel and after the arrangement solution, it filters through theCelite.The filtered material is evaporated in the Rotavapor. Oil is distilled from(1.5 mbar, and the head temperature 135)under the HI-vacuum. The white solid of 168.1 g is isolated (45percent of theTheoretical value)

Reference： [1]Patent: KR2015/142006,2015,A .Location in patent: Paragraph 0149; 0153; 0154

26
[ 7025-06-1 ]
[ 40102-85-0 ]
2,7-dibromocipro-9,9'-xanthene [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
76%		The corresponding Grignard reagent, 10.8g was iodineactivation shavings of waste-like magnesium (410 mmol), 2.6ml (34 mmol) of1,2-dichloroethane and 100ml In a mixture of THF, is prepared from 95.6g of(380 mmol) of 2-bromo-biphenyl phenyl ether [7025-06-1]. When all the magnesiumhad reacted, the solid form 112.0g of (316 mmol) of 2,7-dibromo xanthene[40102-85-0] introduced in portions into the solution, the reaction mixturefurther 6 hours, reflux and stirred under. THF was distilled in 500 ml, allowed to cool suspension to30 ° C. by stirring, was added dropwise rapidly glacial acetic acid 900 ml(Note: exothermic), red a mixture of concentrated sulfuric acid glacial aceticacid and 30ml of 100ml was added dropwise to the solution, the mixture wasstirred for a further 6 hours 60 ° C., allowed to cool to 30 ° C., and ethanol 600 ml, and then400ml of ethanol: water mixture (1: 1 v: v) was added dropwise and the mixtureIt was stirred for a further 1 h, the colorless solid is filtered off with suction, per thetime, twice with glacial acetic acid 150 ml, per the time, 200 ml of ethanol:water mixture (1: 1 v: v) with 2 the degree washed and dried in a vacuum. Thesolid was dissolved in dichloromethane 2000ml, and the insoluble constituentswith suction filtered through a short bed of Celite, the dichloromethane was removedin vacuo, after which the product, once from DMF, recrystallized. Yield: 121.6g(240 mmol), 76percent; purity of about 99.5percent by 1H-NMR.

Reference： [1]Patent: JP2015/519297,2015,A .Location in patent: Paragraph 0094; 0095

27
[ 7025-06-1 ]
C₁₂H₉Cl₂OP [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
		The THF solution (50 mL) of the compound 3 (g [ 7.5 ], 40mmol) was dropped at the roomtemperature at metal magnesium (1 g, 40mmol), 1,2dibromoethane (0.2 mL), and themixture of THF (50 mL), and was stirred into them for 3 hours. The THF solution (20 mL) ofthe phosphorus trichloride (2.6 mL, 30mmol) was dropped here at 78 degree C, and it stirredat the room temperature for 1 hour. It removed under decompression of a solvent and anexcessive phosphorus trichloride, THF (50 mL) was newly added, and the solution of thecompound 4 was obtained. The solution of the compound 2 of the preceding paragraph wasdropped here at 78 degree C, and it stirred at the room temperature for 2 hours to make the solution of the compound 5.

Reference： [1]Patent: JP5812764,2015,B2 .Location in patent: Paragraph 0091-0093

28
[ 7025-06-1 ]
C₃₀H₂₂ClO₃P [ No CAS ]

Reference： [1]Patent: JP5812764,2015,B2

29
[ 7025-06-1 ]
C₃₈H₃₁O₅P [ No CAS ]

Reference： [1]Patent: JP5812764,2015,B2

30
[ 7025-06-1 ]
C₄₄H₃₀F₅O₅P [ No CAS ]

Reference： [1]Patent: JP5812764,2015,B2

31
[ 7025-06-1 ]
C₄₂H₂₆F₅O₄P [ No CAS ]

Reference： [1]Patent: JP5812764,2015,B2

32
[ 7025-06-1 ]
[ 871-91-0 ]
8-(2-phenoxyphenyl)oct-7-yn-1-ol [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
34%	With bis-triphenylphosphine-palladium(II) chloride; copper(l) iodide; N-ethyl-N,N-diisopropylamine; In N,N-dimethyl-formamide; at 70℃;Inert atmosphere;	General procedure: Toasolutionofbromide12(a-c)(0.3mmol)and bis(triphenylphosphine)palladium(II)dichloride(9mumol),N-ethyl-N-isopropylpropan-2-amine(0.3mmol)andcopper(I)iodide(0.03mmol)inDMF(1.5ml)wasaddedtheappropriatealkynerelatedalkyne(0.45mmol)andthevesselwasflushedwithargon,sealedandheated(70°C,overnight).Theresultingdarkmixturewascooledtoroomtemperatureandpurifiedbysilicagelchromatographytoafford13(a-d).

Reference： [1]Bioorganic and Medicinal Chemistry Letters,2016,vol. 26,p. 5009 - 5012

33
[ 928-90-5 ]
[ 7025-06-1 ]
6-(2-phenoxyphenyl)hex-5-yn-1-ol [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
66%	With bis-triphenylphosphine-palladium(II) chloride; copper(l) iodide; N-ethyl-N,N-diisopropylamine; In N,N-dimethyl-formamide; at 70℃;Inert atmosphere;	General procedure: Toasolutionofbromide12(a-c)(0.3mmol)and bis(triphenylphosphine)palladium(II)dichloride(9mumol),N-ethyl-N-isopropylpropan-2-amine(0.3mmol)andcopper(I)iodide(0.03mmol)inDMF(1.5ml)wasaddedtheappropriatealkynerelatedalkyne(0.45mmol)andthevesselwasflushedwithargon,sealedandheated(70°C,overnight).Theresultingdarkmixturewascooledtoroomtemperatureandpurifiedbysilicagelchromatographytoafford13(a-d).

Reference： [1]Bioorganic and Medicinal Chemistry Letters,2016,vol. 26,p. 5009 - 5012

34
[ 7025-06-1 ]
6-(2-phenoxyphenyl)hexan-1-ol [ No CAS ]

Reference： [1]Bioorganic and Medicinal Chemistry Letters,2016,vol. 26,p. 5009 - 5012

35
[ 7025-06-1 ]
8-(2-phenoxyphenyl)octan-1-ol [ No CAS ]

Reference： [1]Bioorganic and Medicinal Chemistry Letters,2016,vol. 26,p. 5009 - 5012

36
[ 7025-06-1 ]
N^α-(((9H-fluoren-9-yl)methoxy)carbonyl)-N^π-(6-(2-phenoxyphenyl)hexyl)-L-histidine [ No CAS ]

Reference： [1]Bioorganic and Medicinal Chemistry Letters,2016,vol. 26,p. 5009 - 5012

37
[ 7025-06-1 ]
N^α-(((9H-fluoren-9-yl)methoxy)carbonyl)-N^π-(6-(2-phenoxyphenyl)octyl)-L-histidine [ No CAS ]

Reference： [1]Bioorganic and Medicinal Chemistry Letters,2016,vol. 26,p. 5009 - 5012

38
[ 7025-06-1 ]
2-bromo-spiro[fluorene-9,9'-xanthene] [ No CAS ]

Reference： [1]Patent: JP2016/505518,2016,A

39
[ 7025-06-1 ]
C₅₂H₃₇NO [ No CAS ]

Reference： [1]Patent: JP2016/505518,2016,A

40
[ 7025-06-1 ]
4,4,5,5-tetramethyl-2-(spiro[fluorene-9,9'-xanthen]-2-yl)-1,3,2-dioxaborolane [ No CAS ]

Reference： [1]Patent: JP2016/505518,2016,A

41
[ 7025-06-1 ]
C₅₅H₃₇NO [ No CAS ]

Reference： [1]Patent: JP2016/505518,2016,A

42
[ 7025-06-1 ]
[ 3096-56-8 ]
C₂₅H₁₇BrO₂ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
		31.7 g (127 mmol) of1-Bromo-2-diphenyl ether,Dissolve in 400 ml of anhydrous THF in a flask which has been dried by heating. Cool the reaction mixture to -78 ° C. At this temperature 55 ml of a 2.5 M solution of n-BuLi in hexane (127 mmol) is slowly added dropwise.The batch was further heated at -70 ° C.Stir for 1 hour.30 g of 2-bromofluorenone (116 mmol)Is dissolved in 100 ml of THF and added dropwise at -70 ° C.Upon completion of the addition, the reaction mixture is warmed slowly to room temperature, warmed up using NH 4 Cl, then evaporated in a rotary evaporator.

Reference： [1]Patent: JP2016/505518,2016,A .Location in patent: Paragraph 0130; 0131

43
[ 7025-06-1 ]
[κ²-(P,O)-2-(PPh(o-MeO-C₆H₄))-1-benzenesulfonato]-NiPh(PPh₃) [ No CAS ]

Reference： [1]Organometallics,2017,vol. 36,p. 2338 - 2344

44
[ 7025-06-1 ]
[κ²-(P,O)-2-(PPh(o-PhO-C₆H₄))-1-benzenesulfonato]Pd(Me)(dmso) [ No CAS ]

Reference： [1]Organometallics,2017,vol. 36,p. 2338 - 2344

45
[ 7025-06-1 ]
[ 98-11-3 ]
C₂₄H₁₉O₄PS [ No CAS ]

Reference： [1]Organometallics,2017,vol. 36,p. 2338 - 2344

46
[ 7025-06-1 ]
[ 14348-75-5 ]
[ 1259293-43-0 ]

Yield	Reaction Conditions	Operation in experiment
		127 mmol of <strong>[7025-06-1]1-bromo-2-diphenyl ether</strong> was dissolved in 400 mL of dry tetrahydrofuran which had been passed through a heated flask and the reaction mixture was cooled to -78 ° C.At this temperature,A solution of 55 mL of n-butyllithium in 2.5 M (127 mmol) hexane was slowly added dropwise.The reaction mixture was stirred at -70 & lt; 0 & gt; C for 1 hour. Subsequently, 30 g of dibromo-9H-fluoren-9-one (116 mmol) was dissolved in 100 mL of tetrahydrofuran and added dropwise at -70 ° C.When the addition was complete, the reaction mixture was allowed to slowly warm to room temperature,Quenched with NH4Cl and then evaporated in a rotary evaporator.

Reference： [1]Patent: CN106632219,2017,A .Location in patent: Paragraph 0067; 0068; 0069; 0070

47
[ 7025-06-1 ]
C₄₅H₂₇N₃O [ No CAS ]

Reference： [1]Patent: KR2017/59910,2017,A

48
[ 7025-06-1 ]
C₄₆H₂₈N₄O [ No CAS ]

Reference： [1]Patent: KR2017/59910,2017,A

49
[ 7025-06-1 ]
C₄₅H₂₇N₃O [ No CAS ]

Reference： [1]Patent: KR2017/59910,2017,A

50
[ 7025-06-1 ]
C₃₁H₁₉NO₃ [ No CAS ]

Reference： [1]Patent: KR2017/59910,2017,A

51
[ 7025-06-1 ]
C₃₁H₁₉NO [ No CAS ]

Reference： [1]Patent: KR2017/59910,2017,A

52
[ 7025-06-1 ]
C₄₉H₂₉N₃O [ No CAS ]

Reference： [1]Patent: KR2017/59910,2017,A

53
[ 7025-06-1 ]
C₄₆H₂₈N₄O [ No CAS ]

Reference： [1]Patent: KR2017/59910,2017,A

54
[ 7025-06-1 ]
C₄₉H₂₉N₃O [ No CAS ]

Reference： [1]Patent: KR2017/59910,2017,A

55
[ 7025-06-1 ]
C₄₆H₂₈N₄O [ No CAS ]

Reference： [1]Patent: KR2017/59910,2017,A

56
[ 7025-06-1 ]
C₃₁H₂₀ClNO [ No CAS ]

Reference： [1]Patent: KR2017/59910,2017,A

57
[ 7025-06-1 ]
C₄₉H₃₀ClN₃O [ No CAS ]

Reference： [1]Patent: KR2017/59910,2017,A

58
[ 7025-06-1 ]
C₄₆H₂₉ClN₄O [ No CAS ]

Reference： [1]Patent: KR2017/59910,2017,A

59
[ 7025-06-1 ]
C₃₁H₁₉NO₃ [ No CAS ]

Reference： [1]Patent: KR2017/59910,2017,A

60
[ 7025-06-1 ]
C₃₁H₁₉NO [ No CAS ]

Reference： [1]Patent: KR2017/59910,2017,A

61
[ 7025-06-1 ]
C₄₉H₂₉N₃O [ No CAS ]

Reference： [1]Patent: KR2017/59910,2017,A

62
[ 7025-06-1 ]
[ 3096-56-8 ]
2-bromo-spiro[fluorene-9,9'-xanthene] [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
32 g		30 g of <strong>[7025-06-1]1-<strong>[7025-06-1]bromo-2-phenoxybenzene</strong></strong> was dissolved in 300 ml of anhydrous tetrahydrofuran under a nitrogen atmosphere,-78 ° CRespectively.to the next,48 ml of 2.5 M-butyllithium was slowly added dropwise.After completion of the dropwise addition, stirring was performed for 30 minutes,2-Bromofluorene 31.2 gWas dissolved in 200 ml of absolute tetrahydrofuran and then slowly added dropwise.The reaction solution was maintained at -78 ° C for about 1 hour, then warmed to room temperature and stirred for 12 hours.The reaction was terminated by adding diluted hydrochloric acid to the reaction solution, followed by liquid fraction extraction using methylene chloride.The obtained organic layer was dried with magnesium sulfate, filtered, and then distilled under reduced pressure. to the next,After adding 400 ml of acetic acid, a catalytic amount of hydrochloric acid was added dropwise, followed by stirring at a reflux temperature for 12 hours.After completion of the reaction, the reaction mixture was cooled to obtain a solid,After filtration, 32.0 g of compound AA was obtained by column chromatography.

Reference： [1]Patent: KR2017/59910,2017,A .Location in patent: Paragraph 0315-0318

63
[ 7025-06-1 ]
[ 643-79-8 ]
C₃₂H₂₆O₄ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
0.7 g		To a tetrahydrofuran (60 mL) solution of <strong>[7025-06-1]1-<strong>[7025-06-1]bromo-2-phenoxybenzene</strong></strong> (6.0 g, 24.1 mmol) was added a n-butyllithium hexane solution (2.5 M, 10.6 mL, 25.6 mmol) at -78 ° C., And the mixture was stirred at room temperature for 2 hours.Phthalaldehyde (1.52 g, 11.4 mmol) was added to the reaction solution,In tetrahydrofuran (10 mL) was added at -78 ° C.,And the mixture was stirred at room temperature for 16 hours.Ice water (50 mL) was added, extracted with ethyl acetate (40 mL × 3) and dried over sodium sulfate.Purification by column chromatography (pentane / ethyl acetate = 20/1) gave Compound 4 as a white solid. The yield was 0.7 g.

Reference： [1]Patent: JP6207336,2017,B2 .Location in patent: Paragraph 0112-0113

64
[ 7025-06-1 ]
1,2-dimethyl-1-phenethyl-4-phenoxy-1H-indene [ No CAS ]

Reference： [1]Angewandte Chemie - International Edition,2017,vol. 56,p. 14591 - 14595
Angew. Chem.,2017,vol. 129,p. 14783 - 14787,5

65
[ 7025-06-1 ]
[ 27081-10-3 ]
[ 1528732-88-8 ]

Reference： [1]Angewandte Chemie - International Edition,2017,vol. 56,p. 14591 - 14595
Angew. Chem.,2017,vol. 129,p. 14783 - 14787,5

66
[ 7025-06-1 ]
[ 69414-97-7 ]
C₂₅H₁₆Br₂O₂ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
		Dissolve 27.4 g (110 mmol) of <strong>[7025-06-1]1-bromo-2-diphenyl ether</strong> in 350 ml of dry tetrahydrofuran,Cool the reaction system to -78 °C50 ml of n-butyllithium in 2.5 M (110 mmol) hexane was slowly added dropwise,Then keep the system stirred at -70°C for 1 hour.Then 33.8 g (100 mmol) of 4,5-dibromo-9H-fluorenone was dissolved in 85 ml of tetrahydrofuran and added dropwise at -70°C.The system was slowly warmed to room temperature, quenched with ammonium chloride and subsequently evaporated in a rotary evaporator, and the organic solution was collected, and the resulting intermediate (A) was dissolved in the organic solution.

Reference： [1]Patent: CN107880053,2018,A .Location in patent: Paragraph 0040; 0053

67
[ 7025-06-1 ]
C₂₅H₁₈B₂O₅ [ No CAS ]

Reference： [1]Patent: CN107880053,2018,A

68
[ 7025-06-1 ]
C₃₇H₂₂N₂O₅ [ No CAS ]

Reference： [1]Patent: CN107880053,2018,A

69
[ 7025-06-1 ]
C₃₇H₂₂N₂O [ No CAS ]

Reference： [1]Patent: CN107880053,2018,A

70
[ 7025-06-1 ]
C₃₁H₂₀BNO₅ [ No CAS ]

Reference： [1]Patent: CN107880053,2018,A

71
[ 7025-06-1 ]
C₃₁H₂₀BNO₃ [ No CAS ]

Reference： [1]Patent: CN107880053,2018,A

72
[ 7025-06-1 ]
C₄₀H₂₈N₂O₃ [ No CAS ]

Reference： [1]Patent: CN107880053,2018,A

73
[ 7025-06-1 ]
C₄₀H₂₈N₂O [ No CAS ]

Reference： [1]Patent: CN107880053,2018,A

74
[ 7025-06-1 ]
C₃₇H₂₄BNO₃ [ No CAS ]

Reference： [1]Patent: CN107880053,2018,A

75
[ 7025-06-1 ]
C₄₃H₂₆N₂O₃ [ No CAS ]

Reference： [1]Patent: CN107880053,2018,A

76
[ 7025-06-1 ]
C₄₃H₂₆N₂O [ No CAS ]

Reference： [1]Patent: CN107880053,2018,A

77
[ 7025-06-1 ]
C₅₅H₃₄N₂O [ No CAS ]

Reference： [1]Patent: CN107880053,2018,A

78
[ 7025-06-1 ]
C₂₅H₁₄Br₂O [ No CAS ]

Reference： [1]Patent: CN107880053,2018,A

79
(2RP,4SC,5RC)-(+)-3,4-dimethyl-2,5-diphenyl-1,3,2-oxazaphospholidine borane [ No CAS ]
[ 7025-06-1 ]
C₂₈H₃₁BNO₂P [ No CAS ]

Reference： [1]European Journal of Organic Chemistry,2018,vol. 2018,p. 2984 - 2994

80
[ 7025-06-1 ]
(R)-(+)-(2-methoxyphenyl)(2-phenoxyphenyl)(phenyl)phosphane borane complex [ No CAS ]

Reference： [1]European Journal of Organic Chemistry,2018,vol. 2018,p. 2984 - 2994

81
[ 7025-06-1 ]
(R)-(-)-(4-methoxyphenyl)(2-phenoxyphenyl)(phenyl)phosphane borane complex [ No CAS ]

Reference： [1]European Journal of Organic Chemistry,2018,vol. 2018,p. 2984 - 2994

82
[ 7025-06-1 ]
(R)-(-)-(2-methoxyphenyl)(2-phenoxyphenyl)(phenyl)phosphane [ No CAS ]

Reference： [1]European Journal of Organic Chemistry,2018,vol. 2018,p. 2984 - 2994

83
[ 7025-06-1 ]
(R)-(+)-(4-methoxyphenyl)(2-phenoxyphenyl)(phenyl)phosphane [ No CAS ]

Reference： [1]European Journal of Organic Chemistry,2018,vol. 2018,p. 2984 - 2994

84
[ 7025-06-1 ]
C₁₉H₂₀BO₂P [ No CAS ]

Reference： [1]European Journal of Organic Chemistry,2018,vol. 2018,p. 2984 - 2994

85
[ 7025-06-1 ]
C₂₄H₁₆Br₃NO₂ [ No CAS ]

Reference： [1]Patent: CN108164543,2018,A

86
[ 7025-06-1 ]
C₂₅H₁₄BrNO₂ [ No CAS ]

Reference： [1]Patent: CN108164543,2018,A

87
[ 7025-06-1 ]
C₂₅H₁₃NO₂ [ No CAS ]

Reference： [1]Patent: CN108164543,2018,A

88
[ 7025-06-1 ]
C₃₇H₂₀BrNO₂ [ No CAS ]

Reference： [1]Patent: CN108164543,2018,A

89
[ 7025-06-1 ]
C₅₃H₃₂N₂O₂ [ No CAS ]

Reference： [1]Patent: CN108164543,2018,A

90
[ 7025-06-1 ]
2,3-di-bromodiphenyl ether [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
81%	With bromine; potassium hydroxide; In chloroform; at 20℃; for 15h;	In a 2 L three-necked flask, 24.9 g (100 mmol, 1.0 eq.) was charged.<strong>[7025-06-1]2-bromodiphenyl ether</strong>,Dissolved in 500 ml of chloroform,Further, 11.2 g (200 mmol, 2.0 eq.) of potassium hydroxide was added.63.9 g (400 mmol, 4.0 eq.) of liquid bromine was added dropwise at room temperature.After the completion of the dropwise addition, the mixture was reacted at room temperature for 15 hours. The reaction was quenched with a saturated Na 2 SO 3 solution.There is a lot of solid precipitation, stirring, suction filtration,Washed with water, washed with ethanol, recrystallized from chloroform and ethanol,Finally, 33 g of Intermediate-1 was obtained in a yield of 81percent.

Reference： [1]Patent: CN108164543,2018,A .Location in patent: Paragraph 0061; 0062; 0064; 0065

91
[ 7025-06-1 ]
C₂₅H₁₄Br₂O₃S [ No CAS ]