[ CAS No. 653-30-5 ] {[proInfo.proName]}

Name: 653-30-5|2-(Perfluorophenyl)acetonitrile|98%
Brand: Ambeed
SKU: A611050
Price: 14.0 USD
Availability: InStock
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Cat. No.: {[proInfo.prAm]}

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Quality Control of [ 653-30-5 ]

COA NMR CNMR HPLC LC-MS

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SDS Specification

Alternatived Products of [ 653-30-5 ]

Product Details of [ 653-30-5 ]

CAS No. :	653-30-5	MDL No. :	MFCD00013814
Formula :	C₈H₂F₅N	Boiling Point :	-
Linear Structure Formula :	-	InChI Key :	YDNOJUAQBFXZCR-UHFFFAOYSA-N
M.W :	207.10	Pubchem ID :	69554
Synonyms :

Calculated chemistry of [ 653-30-5 ] Expand+

Physicochemical Properties

Num. heavy atoms :	14
Num. arom. heavy atoms :	6
Fraction Csp3 :	0.12
Num. rotatable bonds :	1
Num. H-bond acceptors :	6.0
Num. H-bond donors :	0.0
Molar Refractivity :	35.75
TPSA :	23.79 Å²

Pharmacokinetics

GI absorption :	High
BBB permeant :	Yes
P-gp substrate :	No
CYP1A2 inhibitor :	No
CYP2C19 inhibitor :	No
CYP2C9 inhibitor :	No
CYP2D6 inhibitor :	No
CYP3A4 inhibitor :	No
Log Kp (skin permeation) :	-5.99 cm/s

Lipophilicity

Log Po/w (iLOGP) :	1.57
Log Po/w (XLOGP3) :	2.22
Log Po/w (WLOGP) :	4.55
Log Po/w (MLOGP) :	3.89
Log Po/w (SILICOS-IT) :	4.28
Consensus Log Po/w :	3.3

Druglikeness

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

Water Solubility

Log S (ESOL) :	-2.77
Solubility :	0.349 mg/ml ; 0.00168 mol/l
Class :	Soluble
Log S (Ali) :	-2.35
Solubility :	0.916 mg/ml ; 0.00442 mol/l
Class :	Soluble
Log S (SILICOS-IT) :	-4.29
Solubility :	0.0106 mg/ml ; 0.0000512 mol/l
Class :	Moderately soluble

Medicinal Chemistry

PAINS :	0.0 alert
Brenk :	2.0 alert
Leadlikeness :	1.0
Synthetic accessibility :	1.68

Safety of [ 653-30-5 ]

Signal Word:	Danger	Class:	6.1
Precautionary Statements:	P260-P264-P270-P271-P280-P301+P310-P302+P352-P304+P340-P305+P351+P338-P311-P312-P321-P322-P330-P332+P313-P337+P313-P361-P362-P363-P403+P233-P405-P501	UN#:	3276
Hazard Statements:	H301-H311-H315-H319-H331	Packing Group:	Ⅲ
GHS Pictogram:

Application In Synthesis of [ 653-30-5 ]

* 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.

Downstream synthetic route of [ 653-30-5 ]

[ 653-30-5 ] Synthesis Path-Downstream 1~102

1
[ 392-56-3 ]
[ 653-30-5 ]
[ 42238-34-6 ]

Yield	Reaction Conditions	Operation in experiment
25%	With sodium hydride In N,N-dimethyl-formamide Ambient temperature;
	With sodium hydride

Reference： [1]Filler, Robert; Fiebig, August E.; Pelister, M. Yavuz [Journal of Organic Chemistry, 1980, vol. 45, # 7, p. 1290 - 1295]
[2]Vlasov,V.M.; Yakobson,G.G. [Journal of Organic Chemistry USSR (English Translation), 1973, vol. 9, p. 1051 - 1056][Zhurnal Organicheskoi Khimii, 1973, vol. 9, # 5, p. 1024 - 1031]

2
[ 653-30-5 ]
[ 134521-71-4 ]
[ 134521-71-4 ]

Yield	Reaction Conditions	Operation in experiment
	With sodium hydroxide; tetrabutyl-ammonium chloride In tetrachloromethane at 45℃; for 1.5h;

Reference： [1]Nakayama, Yasuhide; Inukai, Kazuo; Hayashi, Koichiro; Irie, Masahiro [Bulletin of the Chemical Society of Japan, 1991, vol. 64, # 4, p. 1226 - 1230]

3
[ 653-30-5 ]
[ 91407-85-1 ]
[ 91407-86-2 ]

Yield	Reaction Conditions	Operation in experiment
1: 10% 2: 25%	With perchloryl fluoride; cesium fluoride In N,N-dimethyl-formamide at 40℃; for 0.666667h;

Reference： [1]Bardin, V. V.; Furin, G. G.; Yakobson, G. G. [Journal of Organic Chemistry USSR (English Translation), 1984, vol. 20, p. 514 - 519][Zhurnal Organicheskoi Khimii, 1984, vol. 20, # 3, p. 567 - 573]

4
[ 143-33-9 ]
[ 1765-40-8 ]
[ 653-30-5 ]

Yield	Reaction Conditions	Operation in experiment
63%	With tetrabutyl-ammonium chloride In tetrahydrofuran; water for 0.166667h;

Reference： [1]Nakayama, Yasuhide; Inukai, Kazuo; Hayashi, Koichiro; Irie, Masahiro [Bulletin of the Chemical Society of Japan, 1991, vol. 64, # 4, p. 1226 - 1230]

5
[ 151-50-8 ]
[ 1765-40-8 ]
[ 653-30-5 ]
[ 124614-44-4 ]

Yield	Reaction Conditions	Operation in experiment
1: 19% 2: 78%	In ethanol at 75 - 80℃; for 0.75h;

Reference： [1]Filler, Robert; Woods, Sarah M.; White, William L. [Canadian Journal of Chemistry, 1989, vol. 67, p. 1837 - 1841]

6
[ 1765-40-8 ]
[ 653-30-5 ]
[ 124614-44-4 ]

Yield	Reaction Conditions	Operation in experiment
1: 78% 2: 19%	With potassium cyanide In ethanol at 75 - 80℃; for 0.75h;

Reference： [1]Filler, Robert; Woods, Sarah M.; White, William L. [Canadian Journal of Chemistry, 1989, vol. 67, p. 1837 - 1841]

7
[ 653-30-5 ]
[ 1583-76-2 ]

Yield	Reaction Conditions	Operation in experiment
85%	Stage #1: (pentafluorophenyl)acetonitrile With aluminum (III) chloride; lithium aluminium tetrahydride In diethyl ether at 20℃; Stage #2: With water In diethyl ether	1 370 mg of LiAIH4 are suspended in 10 ml of dry diethyl ether. 1.24 g of AICb are then dissolved in 6 ml of ether and added rapidly to the suspension. After 5 min, 2.00 g of pentafluorophenylacetonitrile dissolved in 6 ml of ether are slowly added dropwise. After stirring at room temperature for one hour, the remaining LiAIH4 is quenched cautiously with water, then 16 ml of 6N sulfuric acid and 8 ml of water are added. In a separating funnel, the ether phase is removed and the aqueous phase is extracted by shaking twice with 20 ml each time of ether. Finally, the aqueous phase is brought to pH 11 with KOH pellets while cooling with an ice bath, and the aqueous phase is once again extracted by shaking three times with 30 ml each time of ether. These three organic phases are combined and dried over sodium sulfate, and the solvent is removed under gentle vacuum.Yield: 1.70 g (0.85 mmol, 85% of theory)1H NMR (400 MHz, CDCI3, TMS): δ = 2.95 (t, 2H, 3J=7.2 Hz), 2.83 (t, 2H, 3J=7.2 Hz)
81%	With aluminum (III) chloride; lithium aluminium tetrahydride In tetrahydrofuran at 20℃; for 1h;
73%	With lithium aluminium tetrahydride; aluminium trichloride In diethyl ether for 1h;

67%	With sodium tetrahydroborate; trifluoroacetic acid In tetrahydrofuran at 20℃; for 4h; Inert atmosphere;	2-(Pentafluorophenyl)ethanamine (5). To a stirred suspension of NaBH4 (12.4 g, 324 mmol) in dry THF (200mL) under predried argon was added CF3CO2H (36.9 g, 324 mmol) in dry THF (30 mL) over a period of 10 minat 20 oC. 2,3,4,5,6-Pentafluorophenylacetonitrile (4) (67.07 g, 324 mmol) was then added dropwise in dry THF(30 mL), and the mixture was stirred at rt for 4 h after this addition. The excess reagent was then cautiouslydecomposed with H2O below 10 oC in an ice bath, and the resulting mixture was concentrated to dryness invacuo, and extracted with CH2Cl2. The extract was washed with saturated NaHCO3 solution, H2O, and driedover anhydrous Na2SO4. Concentration in vacuo yielded of 5 as a residual green oily layer (45.74 g, 67%), whichwas used without further purification for the preparation of 4,5,6,7-tetrafluoroindole. In order to characterizethe amine, a small amount was distilled to give a colorless liquid; bp 96-102 oC (33 Torr) (lit.27 bp 80-90 oC (20Torr)); IR (neat) 3350, 2940, 2860, 1660, 1525, 1510 cm-1; 1H NMR (CDCl3) δ 1.25 (m, 2H), 3.25 (m, 2H); UV(95% EtOH) λmax 225, 247 nm.
65%	With aluminum (III) chloride; lithium aluminium tetrahydride In tetrahydrofuran for 1h; Inert atmosphere;
50%	With lithium aluminium tetrahydride; aluminium trichloride In tetrahydrofuran at 0℃; for 1h;
	With lithium aluminium tetrahydride
	With LiAlH₄; sulfuric acid In diethyl ether; water	1 Preparation of 2-pentafluorophenylethylamine Example 1 Preparation of 2-pentafluorophenylethylamine 370 mg of LiAlH4 are suspended in 10 ml of dry diethyl ether. 1.24 g of AlCl3 are then dissolved in 6 ml of ether and added rapidly to the suspension. After 5 min, 2.00 g of pentafluorophenylacetonitrile dissolved in 6 ml of ether are slowly added dropwise. After stirring at room temperature for one hour, the remaining LiAlH4 is quenched cautiously with water, then 16 ml of 6N sulfuric acid and 8 ml of water are added. In a separating funnel, the ether phase is removed and the aqueous phase is extracted by shaking twice with 20 ml each time of ether. Finally, the aqueous phase is brought to pH 11 with KOH pellets while cooling with an ice bath, and the aqueous phase is once again extracted by shaking three times with 30 ml each time of ether. These three organic phases are combined and dried over sodium sulfate, and the solvent is removed under gentle vacuum. Yield: 1.70 g (0.85 mmol, 85% of theory) 1H NMR (400 MHz, CDCl3, TMS): δ=2.95 (t, 2H, 3J=7.2 Hz), 2.83 (t, 2H, 3J=7.2 Hz)

Reference： [1]Current Patent Assignee: BASF SE; STANFORD UNIVERSITY - WO2009/115553, 2009, A1 Location in patent: Page/Page column 24
[2]Nguyen, Thuy; Gamage, Thomas F.; Finlay, David B.; Decker, Ann M.; Langston, Tiffany L.; Barrus, Daniel; Glass, Michelle; Li, Jun-Xu; Kenakin, Terry P.; Zhang, Yanan [Journal of Medicinal Chemistry, 2022, vol. 65, # 1, p. 257 - 270]
[3]Filler, Robert; Chen, Wei; Woods, Sarah M. [Journal of Fluorine Chemistry, 1995, vol. 73, # 1, p. 95 - 100]
[4]James Gruver; Onyango, Evans O.; Gribble, Gordon W. [Arkivoc, 2018, vol. 2018, # 3, p. 144 - 152]
[5]Giese, Michael; Albrecht, Markus; Wiemer, Katharina; Valkonen, Arto; Rissanen, Kari [New Journal of Chemistry, 2012, vol. 36, # 6, p. 1368 - 1372]
[6]Das, Biplab Kumar; Shibata, Norio; Takeuchi, Yoshio [Journal of the Chemical Society. Perkin Transactions 1 (2001), 2002, vol. 2, # 2, p. 197 - 206]
[7]Barbour,A.K. et al. [Journal of the Chemical Society, 1961, p. 808 - 817]
[8]Current Patent Assignee: BASF SE; STANFORD UNIVERSITY - US2009/236591, 2009, A1

8
[ 151-50-8 ]
[ 653-35-0 ]
[ 653-30-5 ]

Reference： [1]Journal of the Chemical Society,1961,p. 808 - 817

9
[ 653-30-5 ]
[ 16264-67-8 ]
1-(2'-Pentafluorophenylethyl)-4,5,6,7-tetrafluoroindole [ No CAS ]

Reference： [1]Journal of Fluorine Chemistry,1995,vol. 73,p. 95 - 100

10
[ 653-30-5 ]
[ 19282-55-4 ]
1-(2'-Pentafluorophenylethyl)-4,5,6,7-tetrafluoroindoline [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With hydrogenchloride; potassium fluoride; hydrogen 1.) aq. EtOH, r.t., 1-3 atm, 2.) DMF, reflux, 4 h; Yield given. Multistep reaction;

Reference： [1]Filler, Robert; Chen, Wei; Woods, Sarah M. [Journal of Fluorine Chemistry, 1995, vol. 73, # 1, p. 95 - 100]

11
[ 653-30-5 ]
[ 1583-76-2 ]
Bis(pentafluorophenylethyl)amine [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With hydrogenchloride; hydrogen In ethanol Ambient temperature; Title compound not separated from byproducts;

Reference： [1]Filler, Robert; Chen, Wei; Woods, Sarah M. [Journal of Fluorine Chemistry, 1995, vol. 73, # 1, p. 95 - 100]

12
[ 653-30-5 ]
2-(2,3,4,5,6-Pentafluorophenyl)-acetamidine hydrochloride [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With hydrogenchloride; ammonia 1.) EtOH, a) from 0 deg C to RT, b) RT, 72 h, 2.) EtOH, RT, 3 h; Multistep reaction;

Reference： [1]Li, Qun; Chu, Daniel T. W.; Claiborne, Akiyo; Cooper, Curt S.; Lee, Cheuk M.; Raye, Kathleen; Berst, Kristine B.; Donner, Pamela; Wang, Weibo; Hasvold, Lisa; Fung, Anthony; Ma, Zhenkun; Tufano, Michael; Flamm, Robert; Shen, Linus L.; Baranowski, John; Nilius, Angela; Alder, Jeff; Meulbroek, Jonathan; Marsh, Kennan; Crowell, DeAnne; Hui, Yuhua; Seif, Louis; Melcher, Laura M.; Henry, Rodger; Spanton, Steven; Faghih, Ramin; Klein, Larry L.; Tanaka, S. Ken; Plattner, Jacob J. [Journal of Medicinal Chemistry, 1996, vol. 39, # 16, p. 3070 - 3088]

13
[ 653-30-5 ]
4-Chloro-5-pentafluorophenyl-[1,2,3]dithiazol-2-ylium; chloride [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
63%	With disulfur dichloride; tetrabutyl-ammonium chloride In dichloromethane for 240h;

Reference： [1]Barclay, Tosha M.; Beer, Leanne; Cordes, A. Wallace; Oakley, Richard T.; Preuss, Kathryn E.; Taylor, Nicholas J.; Reed, Robert W. [Chemical Communications, 1999, # 6, p. 531 - 532]

14
[ 6940-76-7 ]
[ 653-30-5 ]
5-chloro-2-pentafluorophenyl-pentanenitrile [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With lithium diisopropyl amide In tetrahydrofuran; cyclohexane at -78 - 20℃; for 1h;

Reference： [1]Ng, Howard P.; Karen, May; Bauman, John G.; Ghannam, Ameen; Islam, Imadul; Liang, Meina; Horuk, Richard; Hesselgesser, Joseph; Snider, R. Michael; Perez, H. Daniel; Morrissey, Michael M. [Journal of Medicinal Chemistry, 1999, vol. 42, # 22, p. 4680 - 4694]

15
[ 653-30-5 ]
[ 2711-79-7 ]
1-(α-cyanopentafluorobenzyl)-4-nitroanthraquinone [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
126 mg	With potassium hydroxide In dimethyl sulfoxide at 20℃; for 0.5h;

Reference： [1]Tabatskaya; Beregovaya [Russian Journal of Organic Chemistry, 2001, vol. 37, # 3, p. 410 - 415]

16
[ 653-30-5 ]
[ 6337-82-2 ]
[ 82-42-8 ]
1-hydroxy-4-(α-cyanopentafluorobenzyl)anthraquinone [ No CAS ]
1-(α-cyanopentafluorobenzyl)-4-nitroanthraquinone [ No CAS ]
2-amino-6-chloro-1,3-bis(pentafluorophenyl)benzanthrone [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With potassium hydride In dimethyl sulfoxide at 20℃; for 0.0833333h; Further byproducts given;

Reference： [1]Tabatskaya; Beregovaya [Russian Journal of Organic Chemistry, 2001, vol. 37, # 3, p. 410 - 415]

17
[ 653-30-5 ]
[ 6337-82-2 ]
[ 81-65-2 ]
1-(α-cyanopentafluorobenzyl)-4-chloroanthraquinone [ No CAS ]
1-(α-cyanopentafluorobenzyl)-4-nitroanthraquinone [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With potassium hydroxide In dimethyl sulfoxide at 20℃; for 0.5h;

Reference： [1]Tabatskaya; Beregovaya [Russian Journal of Organic Chemistry, 2001, vol. 37, # 3, p. 410 - 415]

18
[ 653-30-5 ]
[ 36691-71-1 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 2 steps 1: NaH 2: H₂SO₄ / (heating)
	Multi-step reaction with 3 steps 1: 25 percent / NaH / dimethylformamide / Ambient temperature 2: 27 percent / H₂SO₄ / ethanol / 10 h / Heating 3: 62 percent / p-TsOH / formic acid / 90 h / Heating

Reference： [1]Vlasov,V.M.; Yakobson,G.G. [Journal of Organic Chemistry USSR (English Translation), 1973, vol. 9, p. 1051 - 1056][Zhurnal Organicheskoi Khimii, 1973, vol. 9, # 5, p. 1024 - 1031]
[2]Filler, Robert; Fiebig, August E.; Pelister, M. Yavuz [Journal of Organic Chemistry, 1980, vol. 45, # 7, p. 1290 - 1295]

19
[ 653-30-5 ]
[ 42238-45-9 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 3 steps 1: NaH 2: H₂SO₄ / (heating) 3: H₂SO₄
	Multi-step reaction with 2 steps 1: 25 percent / NaH / dimethylformamide / Ambient temperature 2: 27 percent / H₂SO₄ / ethanol / 10 h / Heating

20
[ 653-30-5 ]
[ 91407-89-5 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 2 steps 1: 10 percent / perchloryl fluoride; cesium fluoride / dimethylformamide / 0.67 h / 40 °C 2: 65 percent / 80percent aq. H₂SO₄; / acetic acid / 48 h / 20 °C

21
[ 653-30-5 ]
[ 91407-90-8 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 3 steps 1: 10 percent / perchloryl fluoride; cesium fluoride / dimethylformamide / 0.67 h / 40 °C 2: 65 percent / 80percent aq. H₂SO₄; / acetic acid / 48 h / 20 °C 3: 91 percent / diethyl ether / overnight

22
[ 653-30-5 ]
[ 91407-88-4 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 3 steps 1: 10 percent / perchloryl fluoride; cesium fluoride / dimethylformamide / 0.67 h / 40 °C 2: 65 percent / 80percent aq. H₂SO₄; / acetic acid / 48 h / 20 °C 3: 60 percent / sulfur tetrafluoride / CH₂Cl₂ / 6 h / 80 °C

23
[ 653-30-5 ]
N-benzyloxycarbonylglycyl-N-(pentafluorophenylethyl)-2-methylalanine (N-tert-butyl)amide [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 2 steps 1: 50 percent / AlCl₃; LiAlH₄ / tetrahydrofuran / 1 h / 0 °C 2: 45 percent / 3 Angstroem molecular sieves / methanol / 20 °C

Reference： [1]Das, Biplab Kumar; Shibata, Norio; Takeuchi, Yoshio [Journal of the Chemical Society. Perkin Transactions 1 (2001), 2002, vol. 2, # 2, p. 197 - 206]

24
[ 653-30-5 ]
[N-benzyloxycarbonylglycyl-N-(pentafluorophenylethyl)-2-methylalanyl]glycine ethyl ester [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 2 steps 1: 50 percent / AlCl₃; LiAlH₄ / tetrahydrofuran / 1 h / 0 °C 2: 51 percent / 3 Angstroem molecular sieves / methanol / 20 °C

Reference： [1]Das, Biplab Kumar; Shibata, Norio; Takeuchi, Yoshio [Journal of the Chemical Society. Perkin Transactions 1 (2001), 2002, vol. 2, # 2, p. 197 - 206]

25
[ 653-30-5 ]
4-(4-Chlorophenyl)-4-hydroxy-α-(2,3,4,5,6-pentafluorophenyl)-1-piperidinepentanenitrile [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 2 steps 1: LDA / cyclohexane; tetrahydrofuran / 1 h / -78 - 20 °C 2: tetrahydrofuran; cyclohexane / 65 °C

26
[ 653-30-5 ]
C₈ClF₅NS₂ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 2 steps 1: 63 percent / S₂Cl₂, n-Bu₄NCl / CH₂Cl₂ / 240 h 2: 27 percent / Ph₃Sb / liquid sulphur dioxide / 0.08 h / -70 °C

27
[ 653-30-5 ]
5-Fluoro-4-hydroxy-2-(2,3,4,5,6-pentafluorobenzyl)pyrimidine [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 2 steps 1: 1.) HCl, 2.) NH₃ / 1.) EtOH, a) from 0 deg C to RT, b) RT, 72 h, 2.) EtOH, RT, 3 h 2: Et₃N / methanol / 23 h / Heating

28
[ 653-30-5 ]
[ 139161-80-1 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 3 steps 1: 1.) HCl, 2.) NH₃ / 1.) EtOH, a) from 0 deg C to RT, b) RT, 72 h, 2.) EtOH, RT, 3 h 2: Et₃N / methanol / 23 h / Heating 3: 1.) n-BuLi / 1.) THF, hexane, -78 deg C, 30 min, 2.) THF, hexane, -78 deg C, 30 min

29
[ 653-30-5 ]
[ 16264-67-8 ]

Reference： [1]Journal of Fluorine Chemistry,1995,vol. 73,p. 95 - 100
[2]Journal of Fluorine Chemistry,1995,vol. 73,p. 95 - 100
[3]Journal of Fluorine Chemistry,1995,vol. 73,p. 95 - 100
[4]Arkivoc,2018,vol. 2018,p. 144 - 152

30
[ 653-30-5 ]
[ 19282-55-4 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 2 steps 1: 73 percent / LiAlH₄, AlCl₃ / diethyl ether / 1 h 2: 61 percent / KF / dimethylformamide / 4 h / Heating
	Multi-step reaction with 2 steps 1: H₂, conc. HCl / PtO₂ / aq. ethanol / 760 - 2280 Torr / Ambient temperature 2: 61 percent / KF / dimethylformamide / 4 h / Heating
	Multi-step reaction with 2 steps 1: sodium tetrahydroborate; trifluoroacetic acid / tetrahydrofuran / 4 h / 20 °C / Inert atmosphere 2: potassium fluoride / N,N-dimethyl-formamide / 3 h / Reflux; Inert atmosphere

Reference： [1]Filler, Robert; Chen, Wei; Woods, Sarah M. [Journal of Fluorine Chemistry, 1995, vol. 73, # 1, p. 95 - 100]
[2]Filler, Robert; Chen, Wei; Woods, Sarah M. [Journal of Fluorine Chemistry, 1995, vol. 73, # 1, p. 95 - 100]
[3]James Gruver; Onyango, Evans O.; Gribble, Gordon W. [Arkivoc, 2018, vol. 2018, # 3, p. 144 - 152]

31
[ 344-04-7 ]
[ 653-30-5 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 4 steps 1: (i) Mg, (ii) /BRN= 636496/ 2: LiAlH₄ 3: PCl₅ 4: aq. ethanol
	Multi-step reaction with 4 steps 1: (i) Mg, (ii) /BRN= 636496/ 2: LiAlH₄ 3: aq. HBr, H₂SO₄ 4: aq. ethanol

Reference： [1]Barbour,A.K. et al. [Journal of the Chemical Society, 1961, p. 808 - 817]
[2]Barbour,A.K. et al. [Journal of the Chemical Society, 1961, p. 808 - 817]

32
[ 653-37-2 ]
[ 653-30-5 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 3 steps 1: LiAlH₄ 2: PCl₅ 3: aq. ethanol
	Multi-step reaction with 3 steps 1: LiAlH₄ 2: aq. HBr, H₂SO₄ 3: aq. ethanol

Reference： [1]Barbour,A.K. et al. [Journal of the Chemical Society, 1961, p. 808 - 817]
[2]Barbour,A.K. et al. [Journal of the Chemical Society, 1961, p. 808 - 817]

33
[ 771-56-2 ]
[ 653-30-5 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 2 steps 1: Cl₂ / Irradiation 2: aq. ethanol
	Multi-step reaction with 4 steps 1: Cl₂ / Irradiation 2: aq. K₂CO₃ / Heating 3: aq. HBr, H₂SO₄ 4: aq. ethanol
	Multi-step reaction with 2 steps 1: Br₂ / Irradiation 2: aq. ethanol

Reference： [1]Barbour,A.K. et al. [Journal of the Chemical Society, 1961, p. 808 - 817]
[2]Barbour,A.K. et al. [Journal of the Chemical Society, 1961, p. 808 - 817]
[3]Barbour,A.K. et al. [Journal of the Chemical Society, 1961, p. 808 - 817]

34
[ 827-15-6 ]
[ 653-30-5 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 4 steps 1: (i) Mg, (ii) /BRN= 906769/ 2: LiAlH₄ 3: PCl₅ 4: aq. ethanol
	Multi-step reaction with 4 steps 1: (i) Mg, (ii) /BRN= 906769/ 2: LiAlH₄ 3: aq. HBr, H₂SO₄ 4: aq. ethanol

Reference： [1]Barbour,A.K. et al. [Journal of the Chemical Society, 1961, p. 808 - 817]
[2]Barbour,A.K. et al. [Journal of the Chemical Society, 1961, p. 808 - 817]

35
[ 440-60-8 ]
[ 653-30-5 ]

Reference： [1]Journal of the Chemical Society,1961,p. 808 - 817
[2]Journal of the Chemical Society,1961,p. 808 - 817

36
[ 653-35-0 ]
[ 653-30-5 ]

Reference： [1]Journal of the Chemical Society,1961,p. 808 - 817

37
[ 653-30-5 ]
[ 106-94-5 ]
[ 1030358-32-7 ]

Yield	Reaction Conditions	Operation in experiment
	With sodium hydroxide; tetrabutylammomium bromide In dodecane; water; chlorobenzene at 35℃; for 24h;

Reference： [1]Makosza, Mieczysław; Chesnokov, Alexey [Tetrahedron, 2008, vol. 64, # 25, p. 5925 - 5932]

38
[ 653-30-5 ]
[ 107-08-4 ]
[ 1030358-32-7 ]

Yield	Reaction Conditions	Operation in experiment
	With sodium hydroxide; tetra-(n-butyl)ammonium iodide In dodecane; water; chlorobenzene at 35℃; for 24h;

Reference： [1]Makosza, Mieczysław; Chesnokov, Alexey [Tetrahedron, 2008, vol. 64, # 25, p. 5925 - 5932]

39
[ 653-30-5 ]
1,2-dicyano-1,2-di(pentafluorophenyl)ethylene [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
64%	With iodine; sodium methylate In methanol

Reference： [1]Location in patent: scheme or table Kayaköy, Selma; Gonca, Ergün [Inorganic Chemistry Communications, 2012, vol. 21, p. 28 - 31]

40
[ 653-30-5 ]
[ 1400280-36-5 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 2 steps 1: ammonia / ethanol; water 2: phosphorus pentoxide / 20 °C

Reference： [1]Moussallem, Chady; Gohier, Frédéric; Mallet, Charlotte; Allain, Magali; Frre, Pierre [Tetrahedron, 2012, vol. 68, # 41, p. 8617 - 8621]

41
[ 653-30-5 ]
[ 1400280-37-6 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 2 steps 1: ammonia / ethanol; water 2: phosphorus pentoxide / 20 °C

Reference： [1]Moussallem, Chady; Gohier, Frédéric; Mallet, Charlotte; Allain, Magali; Frre, Pierre [Tetrahedron, 2012, vol. 68, # 41, p. 8617 - 8621]

42
[ 653-30-5 ]
[ 1400280-38-7 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 2 steps 1: ammonia / ethanol; water 2: phosphorus pentoxide / 20 °C

Reference： [1]Moussallem, Chady; Gohier, Frédéric; Mallet, Charlotte; Allain, Magali; Frre, Pierre [Tetrahedron, 2012, vol. 68, # 41, p. 8617 - 8621]

43
[ 653-30-5 ]
[ 106-51-4 ]
[ 1400280-34-3 ]

Yield	Reaction Conditions	Operation in experiment
40%	With ammonia In ethanol; water	1 7.2.1. 3,7-Bis(perfluorophenyl)benzo[1,2-b:4,5-b']difuran-2,6-diamine: 3 2,3,4,5,6-Pentafluorophenylacetonitrile 2 (7.1 ml, 3 equiv, 55.5 mmol) was added to a solution of 1,4-benzoquinone 1 (2.0 g, 18.5 mmol) in ethanol (50 mL) at room temperature. Then addition of an excess of aqueous solution of ammoniac (7.0 mL) resulted in a fast exothermic reaction and precipitation of a white solid. After 1 h stirring the solid was recovered by filtration and was washed with ethanol (25 mL). Drying under vacuum afforded 3.8 g (40%) of 3 as a white powder, which was used in the next step without any further purification.Mp: 260 °C. 1H NMR (DMSO-d6): 6.98 (s, 2H), 6.68 (s, 4H) ppm 19F NMR (DMSO-d6): -139.7 (dd, 4F, J=6.8 Hz, J=22.4 Hz), -162.3 (t, 2F, J=22.4 Hz), -165.8 (td, 4F, J=6.8 Hz, J=22.4 Hz) ppm 13C NMR (DMF-d7): 157.9, 146.9, 124.2, 108.7, 97.6, 75.5 ppm.IR: 3110, 1481 cm-1. Mass (MALDI-TOF):C22H6F10N2O2, Calcd 520.03 (M+), Found 519.4.Anal. Calcd for C22H6F10N2O2: C, 50.70; H,1.15; N, 5.38. Found: C, 50.59; H, 1.40; N, 5.33.
40%	With ammonium hydroxide
	With ammonium hydroxide In ethanol

With ammonium hydroxide In ethanol Inert atmosphere; Green chemistry;

Reference： [1]Moussallem, Chady; Gohier, Frédéric; Mallet, Charlotte; Allain, Magali; Frre, Pierre [Tetrahedron, 2012, vol. 68, # 41, p. 8617 - 8621]
[2]Moussallem, Chady; Allain, Magali; Gohier, Frédéric; Frère, Pierre [New Journal of Chemistry, 2021, vol. 45, # 19, p. 8647 - 8653]
[3]Moussallem, Chady; Gohier, Frédéric; Frère, Pierre [Tetrahedron Letters, 2015, vol. 56, # 36, p. 5116 - 5119]
[4]Faurie, Alexandre; Grolleau, Jérémie; Gohier, Frédéric; Allain, Magali; Legoupy, Stéphanie; Frère, Pierre [European Journal of Organic Chemistry, 2017, vol. 2017, # 19, p. 2707 - 2714]

44
potassium cyanide [ No CAS ]
[ 1765-40-8 ]
[ 653-30-5 ]

Yield	Reaction Conditions	Operation in experiment
68%	In ethanol; water at 50℃; for 5h;
46%	In ethanol; water at 50℃; for 5h;	As you can see in the above Scheme 12, 2 500 ml - neck (neck) in a flask, potassium cyanide (Potassium cyanide) (2.5 g, 38.3mmol) and the mixture is dissolved in 50 ml water. Ethanol (Ethanol) was added to 2,3,4,5,6-pentafluoro-benzyl bromide dissolved in 110 ml (Pentafluorobenzyl bromide) (10 g, 38.3 mmol) and the mixture was stirred for 5 hours at 50° C . Diethyl ether (Diethyl ether) to the extraction, and then distilled under reduced pressure, and then the dichloromethane (dichloromethane) and hexane (hexane) used for the column chromatography to 3.6 g (46%) of compound was obtained.

Reference： [1]Giese, Michael; Albrecht, Markus; Wiemer, Katharina; Valkonen, Arto; Rissanen, Kari [New Journal of Chemistry, 2012, vol. 36, # 6, p. 1368 - 1372]
[2]Current Patent Assignee: LG DISPLAY CO.,LTD. - KR2016/83249, 2016, A Location in patent: Paragraph 0081; 0082; 0083

45
[ 653-30-5 ]
cis-1,2-dicyano-1,2-di(pentafluorophenyl)ethylene [ No CAS ]
trans-1,2-dicyano-1,2-di(pentafluorophenyl)ethylene [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
16 % de	With potassium <i>tert</i>-butylate; iodine In tetrahydrofuran at 0 - 20℃; Overall yield = 0.9 g;

Reference： [1]Stuzhin, Pavel A.; Goryachev, Maksim Yu.; Ivanova, Svetlana S.; Nazarova, Anna; Pimkov, Igor; Koifman, Oscar I. [Journal of Porphyrins and Phthalocyanines, 2013, vol. 17, # 8-9, p. 905 - 912]

46
[ 823-82-5 ]
[ 653-30-5 ]
C₂₂H₄F₁₀N₂O [ No CAS ]
C₂₂H₄F₁₀N₂O [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
1: 15% 2: 40%	Stage #1: 2,5-diformylfurane; (pentafluorophenyl)acetonitrile With potassium <i>tert</i>-butylate In ethanol at 20℃; for 2.25h; Stage #2: With ammonium chloride In water

Reference： [1]Mallet, Charlotte; Moussallem, Chady; Faurie, Alexandre; Allain, Magali; Gohier, Frédéric; Skene, William G.; Frère, Pierre [Chemistry - A European Journal, 2015, vol. 21, # 21, p. 7944 - 7953]

47
[ 823-82-5 ]
[ 653-30-5 ]
C₂₂H₄F₁₀N₂O [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
45%	With ammonium hydroxide In ethanol for 1h;

48
[ 653-30-5 ]
2,6-N-di[(5’-hexylthiophene-2’-yl)carboxylimino]-benzo[1,2-b:4,5-b’]difuran-3,7-di-pentafluorophenyl [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 2 steps 1: ammonium hydroxide / ethanol 2: phosphorus pentoxide / ethyl acetate

Reference： [1]Moussallem, Chady; Gohier, Frédéric; Frère, Pierre [Tetrahedron Letters, 2015, vol. 56, # 36, p. 5116 - 5119]

49
[ 653-30-5 ]
2,6-N-di[(3’,4’-dihexyloxythiophene-2’-yl)carboxylimino]-benzo[1,2-b:4,5-b’]difuran-3,7-di-pentafluorophenyl [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 2 steps 1: ammonium hydroxide / ethanol 2: phosphorus pentoxide / ethyl acetate

Reference： [1]Moussallem, Chady; Gohier, Frédéric; Frère, Pierre [Tetrahedron Letters, 2015, vol. 56, # 36, p. 5116 - 5119]

50
[ 653-30-5 ]
[ 109-77-3 ]
C₁₁H₃F₄N₃ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
66%	With sodium hydride In tetrahydrofuran at 70℃; for 18h;

Reference： [1]Li, Jun; Zhang, Guangwu; Holm, Daniella M.; Jacobs, Ian E.; Yin, Bin; Stroeve, Pieter; Mascal, Mark; Moulé, Adam J. [Chemistry of Materials, 2015, vol. 27, # 16, p. 5765 - 5774]

51
methyl 2-cyano-2-(pentafluorophenyl)acetate [ No CAS ]
[ 653-30-5 ]

Yield	Reaction Conditions	Operation in experiment
75%	With sulfuric acid; acetic acid In water for 15h; Reflux;

Reference： [1]Li, Jun; Zhang, Guangwu; Holm, Daniella M.; Jacobs, Ian E.; Yin, Bin; Stroeve, Pieter; Mascal, Mark; Moulé, Adam J. [Chemistry of Materials, 2015, vol. 27, # 16, p. 5765 - 5774]

52
[ 392-56-3 ]
[ 653-30-5 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 2 steps 1: potassium carbonate / N,N-dimethyl-formamide / 6 h / 115 °C 2: acetic acid; sulfuric acid / water / 15 h / Reflux
	Multi-step reaction with 2 steps 1: potassium carbonate / N,N-dimethyl-formamide / 48 h / 20 °C 2: sulfuric acid; acetic acid / 16 h / Reflux
	Multi-step reaction with 2 steps 1: potassium carbonate / N,N-dimethyl-formamide; water / 3 h / 110 - 120 °C / Inert atmosphere 2: acetic acid; sulfuric acid / Reflux; Inert atmosphere

Multi-step reaction with 2 steps 1: potassium carbonate / N,N-dimethyl-formamide / 48 h / 20 °C 2: acetic acid; sulfuric acid / water / 16.5 h / 20 °C / Reflux

Reference： [1]Li, Jun; Zhang, Guangwu; Holm, Daniella M.; Jacobs, Ian E.; Yin, Bin; Stroeve, Pieter; Mascal, Mark; Moulé, Adam J. [Chemistry of Materials, 2015, vol. 27, # 16, p. 5765 - 5774]
[2]Current Patent Assignee: SAMSUNG SDI CO.,LTD.; DIC CORP. - CN102892859, 2016, B Current Patent Assignee: DIC CORP.; SAMSUNG SDI CO.,LTD. - TWI526418, 2016, B
[3]James Gruver; Onyango, Evans O.; Gribble, Gordon W. [Arkivoc, 2018, vol. 2018, # 3, p. 144 - 152]
[4]Current Patent Assignee: CHANGCHUN HAIPU RUNSI TECHNOLOGY CO LTD - CN109134311, 2019, A

53
[ 653-30-5 ]
C₁₃H₅F₄N₃O₂ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 2 steps 1: sodium hydride / tetrahydrofuran / 18 h / 70 °C 2: sodium hydride / tetrahydrofuran / 48 h / 80 °C

Reference： [1]Li, Jun; Zhang, Guangwu; Holm, Daniella M.; Jacobs, Ian E.; Yin, Bin; Stroeve, Pieter; Mascal, Mark; Moulé, Adam J. [Chemistry of Materials, 2015, vol. 27, # 16, p. 5765 - 5774]

54
[ 653-30-5 ]
C₂₀H₁₉F₄N₃O₂ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 3 steps 1: sodium hydride / tetrahydrofuran / 18 h / 70 °C 2: sodium hydride / tetrahydrofuran / 48 h / 80 °C 3: toluene-4-sulfonic acid / toluene / 9 h / 85 °C

Reference： [1]Li, Jun; Zhang, Guangwu; Holm, Daniella M.; Jacobs, Ian E.; Yin, Bin; Stroeve, Pieter; Mascal, Mark; Moulé, Adam J. [Chemistry of Materials, 2015, vol. 27, # 16, p. 5765 - 5774]

55
[ 653-30-5 ]
C₂₀H₁₇F₄N₃O₂ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 4 steps 1: sodium hydride / tetrahydrofuran / 18 h / 70 °C 2: sodium hydride / tetrahydrofuran / 48 h / 80 °C 3: toluene-4-sulfonic acid / toluene / 9 h / 85 °C 4: bromine / water / 1.5 h

Reference： [1]Li, Jun; Zhang, Guangwu; Holm, Daniella M.; Jacobs, Ian E.; Yin, Bin; Stroeve, Pieter; Mascal, Mark; Moulé, Adam J. [Chemistry of Materials, 2015, vol. 27, # 16, p. 5765 - 5774]

56
[ 653-30-5 ]
tetrafluoromethyl-oxycarbonyltricyanoquinodimethane [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 3 steps 1: sodium hydride / tetrahydrofuran / 18 h / 70 °C 2: sodium hydride / tetrahydrofuran / 48 h / 80 °C 3: bromine / water / 1 h

Reference： [1]Li, Jun; Zhang, Guangwu; Holm, Daniella M.; Jacobs, Ian E.; Yin, Bin; Stroeve, Pieter; Mascal, Mark; Moulé, Adam J. [Chemistry of Materials, 2015, vol. 27, # 16, p. 5765 - 5774]

57
[ 653-30-5 ]
C₁₇H₇F₆NO₂ [ No CAS ]
C₃₃H₇F₁₆N₃ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
25%	With pyridine; titanium tetrachloride In dichloromethane at -78 - 20℃; for 16h;	In the above reaction scheme 14. As you can see, 500 ml 2 - neck (neck) to the flask obtained in scheme 7 compound (2.0 g, 5.4mmol), the compound obtained in Scheme 12 (11.2 g, 54 mmol) were placed in dichloromethane (dichloromethane ) was dissolved in 300 ml, titanium (IV) chloride (5.9 ml, 54 mmol) and pyridine (pyridine) (8.7 ml, was added dropwise 108 mmol) slowly at -78 in turn. And the mixture was stirred under reflux for 16 hours. After the dropwise addition of distilled water under an ice bath (Ice bath) to terminate the reaction, distilled water and dichloromethane (dichloromethane) in the work-up (work up) and then with dichloromethane (dichloromethane) and hexane (hexane) by column chromatography. 1.0 g was obtained of the compound A41 (25%).

Reference： [1]Current Patent Assignee: LG DISPLAY CO.,LTD. - KR2016/83249, 2016, A Location in patent: Paragraph 0088; 0089; 0090

58
[ 653-30-5 ]
C₂₀H₇F₆N₃O [ No CAS ]
C₂₈H₇F₁₁N₄ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
44%	With pyridine; titanium tetrachloride In dichloromethane at -78 - 20℃; for 16h;	As shown in Scheme 13 above, 500 ml 2- neck (neck) of the compound obtained in Reaction Scheme 9, to the flask (0.84 g, 2.0mmol), compound (2.1 g, 10 mmol) obtained in Scheme 12 into dichloromethane (dichloromethane ) was dissolved in 250 ml, it was added dropwise titanium (IV) chloride (1.1 ml, 10 mmol) and pyridine (pyridine) (1.6 ml, 20 mmol) slowly at -78° C in turn. And the mixture was stirred under reflux for 16 hours. After the dropwise addition of distilled water under an ice bath (Ice bath) to terminate the reaction, distilled water and dichloromethane (dichloromethane) in the work-up (work up) and then with dichloromethane (dichloromethane) and hexane (hexane) by column chromatography. compound A40 was obtained in 0.54 g (44%)

Reference： [1]Current Patent Assignee: LG DISPLAY CO.,LTD. - KR2016/83249, 2016, A Location in patent: Paragraph 0084; 0085; 0086

59
[ 653-30-5 ]
[ 1510834-44-2 ]
C₃₀H₆F₁₀N₂S₂ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
68%	Stage #1: (pentafluorophenyl)acetonitrile With sodium hydride In tetrahydrofuran; mineral oil at 0 - 20℃; for 1h; Stage #2: 5,10-dibromo-naphtho[1,2-b:5,6-b']dithiophene With 1,1'-bis-(diphenylphosphino)ferrocene; tetrakis(triphenylphosphine) palladium⁽⁰⁾ In tetrahydrofuran; mineral oil for 10h; Heating;	3 Synthesis of Compound 3 Acetonitrile Aryl (207 mg, 1.0 mmol) and THF (5 mL) and dissolved in sodium hydride (60% in oil, 50 mg, 1.3 mmol) in at 0 ° C was added slowly and then for 1 hour at room temperature, stirring was dongan. Tetrakis (triphenylphosphine) palladium (58 mg, 0.05 mmol), 1,1'-bis (diphenylphosphino) ferrocene (55 mg, 0.1 mmol), 5,10-dibromonaphtho [1,2-b: 5,6-b '] added dithiophene (200 mg, 0.5 mmol) and the resulting mixture was stirred under heating for 10 hours. After the reaction was completed, it cooled to room temperature to give put water (10 mL) and HCl (1 M, 3 mL) was stirred for 1 hour. The resulting solid product was filtered and then washed with water and methanol. Was added to acetonitrile (10mL) added to the obtained solid to give an aqueous solution of bromine (2 mL) was stirred for 30 minutes. Again filtered and washed with acetonitrile, ethanol, hexane. Next, wash with hot chlorobenzene to obtain a solid-state compounds of three reddish black. (0.221mg, 68% yield)

Reference： [1]Current Patent Assignee: LG DISPLAY CO.,LTD. - KR2016/83235, 2016, A Location in patent: Paragraph 0110-0113

60
[ 823-82-5 ]
[ 653-30-5 ]
(Z)-5-(2-(perfluorophenyl)-2-cyanovinyl)furan-2-carbaldehyde [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
309 mg	With piperidine In chloroform Reflux;

Reference： [1]Faurie, Alexandre; Mallet, Charlotte; Allain, Magali; Skene; Frère, Pierre [New Journal of Chemistry, 2016, vol. 40, # 8, p. 6728 - 6734]

61
[ 823-82-5 ]
[ 653-30-5 ]
C₂₁H₅F₁₀NO [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 2 steps 1: piperidine / chloroform / Reflux 2: metal tert-butoxide / tetrahydrofuran / 2 h / 20 °C / Inert atmosphere

Reference： [1]Faurie, Alexandre; Mallet, Charlotte; Allain, Magali; Skene; Frère, Pierre [New Journal of Chemistry, 2016, vol. 40, # 8, p. 6728 - 6734]

62
[ 653-30-5 ]
2-[-2,3-bis[cyano(2,3,4,5,6-pentafluorophenyl)methylidene]cyclopropylidene]-2-(2,3,4,5,6-pentafluorophenyl)acetonitrile [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Stage #1: (pentafluorophenyl)acetonitrile With lithium hydride In diethylene glycol dimethyl ether at 0 - 20℃; for 0.25h; Stage #2: tetrachlorocyclopropane In diethylene glycol dimethyl ether at 0 - 20℃; for 44h; Stage #3: With hydrogen bromide; nitric acid; acetic acid for 1.5h;	Synthesis of radiotriene compounds General procedure: Lithium hydride (98%) was suspended in 600 ml of glyme and cooled to 0 ° C. 152 mmol of arylacetonitrile (k-o) was slowly added dropwise60 ml of glycolDimethyl ether. The ice bath was removed, and the mixture was heated to room temperature. After 15 minutes of stirring at room temperature, the mixture was recooled to 0 ° C and 40 mmol of tetrachlorocyclopropane was slowly added dropwise to 40 ml of glycolDimethyl ether. Stirring was continued for 44 hours after heating to room temperature. The mixture was then added to 1.2 liters of ice water and acidified with hydrochloric acid (ρ H = 1). The aqueous solution was extracted three times with 500 ml each of ethyl acetate and the cleaned organic phase was first washed with a saturated edible salt solution, then with water, then with sodium bicarbonate solution and finally with water. Dried over magnesium sulfate and the solvent removed in vacuo. The retained dark brown oil was used in the next synthesis without purification. The material was dissolved in 1.4 liters of glacial acetic acid and mixed in a dropwise manner with stirring under a pre-prepared mixture of 360 ml (48%) of hydrobromic acid and 120 ml (65%) of nitric acid. Stir for 1.5 hours and then filter. The red solid was washed with water,Dried in vacuum and subsequently purified by gradient sublimation (p_t)

Reference： [1]Current Patent Assignee: SAMSUNG SDI CO.,LTD.; DIC CORP. - CN102892859, 2016, B Location in patent: Paragraph 0073; 0076

63
[ 2340-87-6 ]
[ 653-30-5 ]

Yield	Reaction Conditions	Operation in experiment
97%	With sulfuric acid; acetic acid In water at 20℃; for 16.5h; Reflux;	2.2 Step2: Add in the reactorIntermediate A-2-1 (2.79 g, 10 mmol),50% acetic acid (4.10 mL) and sulfuric acid (0.2 mL),Stir after 16 hours of reflux,After the mixture is cooled to room temperature,The reaction was terminated by dropwise addition of 10 mL of cold distilled water.After stirring for 0.5 h,The reaction mixture was extracted with distilled water and chloroform.It was then concentrated to give intermediate A-2-2 (1.95 g, 97%).
82%	With sulfuric acid; acetic acid Reflux; Inert atmosphere;	2,3,4,5,6-Pentafluorophenylacetonitrile (4). Ethyl a-cyanopentafluorophenylacetate (105.3 g, 397 mmol) was refluxed for 12 h in 50% AcOH (300 mL) containing H2SO4 (conc., 10 mL). The mixture was then cooled to rt,diluted with an equal volume of H2O, stirred, and a viscous, dark layer settled to the bottom of the flask. The mixture was chilled in an ice bath, the top layer was decanted until the remaining mixture consisted mostly of the dark layer, which was then transferred to a separatory funnel, where the remaining water layer was removed. The dark layer was then extracted with Et2O, and the ethereal layers were combined, washed withH2O, saturated NaHCO3 solution, and dried (MgSO4) to yield 79.74 g of crude pentafluorophenylacetonitrile.Distillation gave 67.1 g (324 mmol, 82%) of 4: bp 65 oC (0.20 Torr) (lit.27 bp 105-107 oC (8 Torr)). IR (neat) 2975,2260, 1660, 1540, 1140 cm-1; mass spectrum, m/e 207 (M+, 100%), 188, 181, 161, 157, 117, 93, 69.
	With sulfuric acid; acetic acid for 16h; Reflux;	Aryl cyanoacetate (FJ) of the whole amount in 84ml of acetic acid (50%) with 4.15ml of concentrated sulfuric acid were heated together to reflux for 16 hours manner.After cooling, pour the entire amount was poured onto 120ml of ice water and stirred for 30 minutes.Phase separation occurs and the aqueous phase extracted with chloroform use 100ml.Purified organic phase and subsequent use 100ml water to wash use 100ml saturated sodium bicarbonate.After drying over magnesium sulfate and the solvent was removed, in accordance with the vacuum distillation as a colorless oil (ko).

With sulfuric acid; acetic acid for 16h; Reflux;

Synthesis of 3-carboxylene Compounds General procedure: The whole amount of arylcyanoacetate (f-j) was heated with reflux of 415 ml of concentrated sulfuric acid in 84 ml of acetic acid (50%) for 16 hours. After cooling, the whole amount was poured into 120 ml of ice water and stirred for 30 minutes. The phases were separated and the aqueous phase was extracted with 10 ml of chloroform. The organic phase was then washed with 100 m of ice and washed with 100 ml of saturated sodium carbonate solution. After drying with magnesium sulfate and after removal of the solvent, the remaining material was distilled in vacuo to give a colorless oil (k-o).

Reference： [1]Current Patent Assignee: CHANGCHUN HAIPU RUNSI TECHNOLOGY CO LTD - CN109134311, 2019, A Location in patent: Paragraph 0090; 0091; 0093
[2]James Gruver; Onyango, Evans O.; Gribble, Gordon W. [Arkivoc, 2018, vol. 2018, # 3, p. 144 - 152]
[3]Current Patent Assignee: SAMSUNG SDI CO.,LTD.; DIC CORP. - CN102892859, 2016, B Location in patent: Paragraph 0075
[4]Current Patent Assignee: DIC CORP.; SAMSUNG SDI CO.,LTD. - TWI526418, 2016, B Location in patent: Paragraph 0052

64
[ 6262-42-6 ]
[ 653-30-5 ]
2-[-2,3-bis[cyano(2,3,4,5,6-pentafluorophenyl)methylidene]cyclopropylidene]-2-(2,3,4,5,6-pentafluorophenyl)acetonitrile [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Stage #1: (pentafluorophenyl)acetonitrile With lithium hydride at 0 - 20℃; for 0.25h; Stage #2: 1,2,3,3-tetrachlorocyclopropene at 0 - 40℃;	Synthesis of 3-carboxylene Compounds General procedure: lithium hydride (98%) was suspended in 600 mL of polyethylene glycol dimethyl ether and cooled to 0 °C. A 52 mmo aryl acetonitrile (k-o) was added dropwise to 60 mL of polyethylene glycol dimethyl ether. Remove the ice bath and allow the reaction to warm to room temperature. After stirring at room temperature for 15 minutes' the mixture was again cooled to 0 °C and 40.0 °C was slowly added dropwise to 40 mL of polyethylene glycol dimethyl ether. The mixture was then forced to 1.2 U water and acidified with hydrochloric acid (ρΗ = 1). Will be extracted three times by shaking the aqueous solution, each of which is extracted with 50 mL of ethyl acetate and the organic phase is washed first in a saturated saline solution and then washed with water and then with sodium bicarbonate Wash 'and finally wash again with water. It was dried over magnesium sulfate and the solvent was removed in vacuo. Will be left deepThe brown oil was used in the following synthesis without further purification The material was dissolved in 1.4 U7JC acetic acid and the previously prepared mixture of 360 mL hydrobromic acid (48%) and 120 mL nitric acid (65%) was added dropwise with stirring. The mixture was stirred for 1.5 hours and then filtered. The resulting red solid was washed with water, dried in vacuo, and then purified by gradient sublimation (p-t).

Reference： [1]Current Patent Assignee: DIC CORP.; SAMSUNG SDI CO.,LTD. - TWI526418, 2016, B Location in patent: Paragraph 0053

65
[ 653-30-5 ]
C₂₆H₂₈N₂O₂ [ No CAS ]
C₄₂H₂₈F₁₀N₄ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
61%	With pyridine; titanium tetrachloride In dichloromethane for 24h;	2 Example 2: Preparation of Compound HT1 4.01 g (10 mmol) of intermediate A-1, 9.53 g (46 mmol)2,3,4,5,6-pentafluorophenylacetonitrile,17.26 g (91 mmol) of titanium tetrachloride was added to the reaction flask.Add 7.2 ml (91 mmol) of pyridine and 58 ml of dichloromethane.Reaction for 24 hours,Filtering,The filtrate is distilled off under reduced pressure to remove the organic solvent.Purification by column chromatography with ethyl acetate/cyclohexane system.Finally recrystallized in a dichloromethane/petroleum ether system,4.75 g (6.1 mmol) of compound HT1 (yield 61%) was obtained.

Reference： [1]Current Patent Assignee: CHANGCHUN HAIPU RUNSI TECHNOLOGY CO LTD - CN108276416, 2018, A Location in patent: Paragraph 0058; 0059

66
[ 653-30-5 ]
4-[(4,5,6,7-tetrafluoroindol-2-yl)carbonyl]pyridine-3-carboxylic acid [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 6 steps 1.1: sodium tetrahydroborate; trifluoroacetic acid / tetrahydrofuran / 4 h / 20 °C / Inert atmosphere 2.1: potassium fluoride / N,N-dimethyl-formamide / 3 h / Reflux; Inert atmosphere 3.1: sodium hydroxide / water / 10 h / 20 °C / Inert atmosphere 4.1: N-Bromosuccinimide; dibenzoyl peroxide / tetrachloromethane / 12 h / Reflux; Inert atmosphere 5.1: lithium diisopropyl amide / tetrahydrofuran; hexane / 4 h / -50 - 20 °C / Inert atmosphere 5.2: -100 - 20 °C / Inert atmosphere 6.1: potassium carbonate / water; methanol / 4.5 h / Inert atmosphere; Reflux
	Multi-step reaction with 6 steps 1.1: sodium tetrahydroborate; trifluoroacetic acid / tetrahydrofuran / 4 h / 20 °C / Inert atmosphere 2.1: potassium fluoride / N,N-dimethyl-formamide / 3 h / Reflux; Inert atmosphere 3.1: manganese(IV) oxide / benzene / 60 h / 20 - 30 °C / Molecular sieve; Inert atmosphere 4.1: lithium diisopropyl amide / tetrahydrofuran; hexane / 8.67 h / -78 - 20 °C / Inert atmosphere 4.2: -78 - 20 °C / Inert atmosphere 5.1: lithium diisopropyl amide / tetrahydrofuran; hexane / 4 h / -50 - 20 °C / Inert atmosphere 5.2: -100 - 20 °C / Inert atmosphere 6.1: potassium carbonate / water; methanol / 4.5 h / Inert atmosphere; Reflux

Reference： [1]James Gruver; Onyango, Evans O.; Gribble, Gordon W. [Arkivoc, 2018, vol. 2018, # 3, p. 144 - 152]
[2]James Gruver; Onyango, Evans O.; Gribble, Gordon W. [Arkivoc, 2018, vol. 2018, # 3, p. 144 - 152]

67
[ 653-30-5 ]
7,8,9,10-tetrafluoroindolo[2,1-g]isoquinoline-5,12-dione [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 7 steps 1.1: sodium tetrahydroborate; trifluoroacetic acid / tetrahydrofuran / 4 h / 20 °C / Inert atmosphere 2.1: potassium fluoride / N,N-dimethyl-formamide / 3 h / Reflux; Inert atmosphere 3.1: manganese(IV) oxide / benzene / 60 h / 20 - 30 °C / Molecular sieve; Inert atmosphere 4.1: lithium diisopropyl amide / tetrahydrofuran; hexane / 8.67 h / -78 - 20 °C / Inert atmosphere 4.2: -78 - 20 °C / Inert atmosphere 5.1: lithium diisopropyl amide / tetrahydrofuran; hexane / 4 h / -50 - 20 °C / Inert atmosphere 5.2: -100 - 20 °C / Inert atmosphere 6.1: potassium carbonate / water; methanol / 4.5 h / Inert atmosphere; Reflux 7.1: acetic anhydride / 24 h / 80 - 90 °C / Inert atmosphere
	Multi-step reaction with 7 steps 1.1: sodium tetrahydroborate; trifluoroacetic acid / tetrahydrofuran / 4 h / 20 °C / Inert atmosphere 2.1: potassium fluoride / N,N-dimethyl-formamide / 3 h / Reflux; Inert atmosphere 3.1: sodium hydroxide / water / 10 h / 20 °C / Inert atmosphere 4.1: N-Bromosuccinimide; dibenzoyl peroxide / tetrachloromethane / 12 h / Reflux; Inert atmosphere 5.1: lithium diisopropyl amide / tetrahydrofuran; hexane / 4 h / -50 - 20 °C / Inert atmosphere 5.2: -100 - 20 °C / Inert atmosphere 6.1: potassium carbonate / water; methanol / 4.5 h / Inert atmosphere; Reflux 7.1: acetic anhydride / 24 h / 80 - 90 °C / Inert atmosphere

68
[ 653-30-5 ]
1-(phenylsulfonyl)-4,5,6,7-tetrafluoroindoline [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 3 steps 1: sodium tetrahydroborate; trifluoroacetic acid / tetrahydrofuran / 4 h / 20 °C / Inert atmosphere 2: potassium fluoride / N,N-dimethyl-formamide / 3 h / Reflux; Inert atmosphere 3: sodium hydroxide / water / 10 h / 20 °C / Inert atmosphere

Reference： [1]James Gruver; Onyango, Evans O.; Gribble, Gordon W. [Arkivoc, 2018, vol. 2018, # 3, p. 144 - 152]

69
[ 653-30-5 ]
1-(phenylsulfonyl)-4,5,6,7-tetrafluoroindole [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 4 steps 1.1: sodium tetrahydroborate; trifluoroacetic acid / tetrahydrofuran / 4 h / 20 °C / Inert atmosphere 2.1: potassium fluoride / N,N-dimethyl-formamide / 3 h / Reflux; Inert atmosphere 3.1: manganese(IV) oxide / benzene / 60 h / 20 - 30 °C / Molecular sieve; Inert atmosphere 4.1: lithium diisopropyl amide / tetrahydrofuran; hexane / 8.67 h / -78 - 20 °C / Inert atmosphere 4.2: -78 - 20 °C / Inert atmosphere
	Multi-step reaction with 4 steps 1: sodium tetrahydroborate; trifluoroacetic acid / tetrahydrofuran / 4 h / 20 °C / Inert atmosphere 2: potassium fluoride / N,N-dimethyl-formamide / 3 h / Reflux; Inert atmosphere 3: sodium hydroxide / water / 10 h / 20 °C / Inert atmosphere 4: N-Bromosuccinimide; dibenzoyl peroxide / tetrachloromethane / 12 h / Reflux; Inert atmosphere

70
[ 653-30-5 ]
4-[1-(phenylsulfonyl)-4,5,6,7-tetrafluoroindol-2-yl]carbonyl}pyridine-3-carboxylic acid [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 5 steps 1.1: sodium tetrahydroborate; trifluoroacetic acid / tetrahydrofuran / 4 h / 20 °C / Inert atmosphere 2.1: potassium fluoride / N,N-dimethyl-formamide / 3 h / Reflux; Inert atmosphere 3.1: sodium hydroxide / water / 10 h / 20 °C / Inert atmosphere 4.1: N-Bromosuccinimide; dibenzoyl peroxide / tetrachloromethane / 12 h / Reflux; Inert atmosphere 5.1: lithium diisopropyl amide / tetrahydrofuran; hexane / 4 h / -50 - 20 °C / Inert atmosphere 5.2: -100 - 20 °C / Inert atmosphere
	Multi-step reaction with 5 steps 1.1: sodium tetrahydroborate; trifluoroacetic acid / tetrahydrofuran / 4 h / 20 °C / Inert atmosphere 2.1: potassium fluoride / N,N-dimethyl-formamide / 3 h / Reflux; Inert atmosphere 3.1: manganese(IV) oxide / benzene / 60 h / 20 - 30 °C / Molecular sieve; Inert atmosphere 4.1: lithium diisopropyl amide / tetrahydrofuran; hexane / 8.67 h / -78 - 20 °C / Inert atmosphere 4.2: -78 - 20 °C / Inert atmosphere 5.1: lithium diisopropyl amide / tetrahydrofuran; hexane / 4 h / -50 - 20 °C / Inert atmosphere 5.2: -100 - 20 °C / Inert atmosphere

71
[ 653-30-5 ]
C₁₆Br₂F₅N₅ [ No CAS ]
C₃₂H₂F₁₅N₇ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
84%	With potassium phosphate; dicyclohexyl-({2-[2-(dicyclohexylphosphanyl)phenyl]-phenyl})-phosphane; palladium diacetate In 1,4-dioxane at 80℃; for 24h;	4 Preparation of intermediate D-1: 5.17 g (10 mmol) of intermediate C, 6 · 21 g (30 mmol) of 2,3,4,5,6-pentafluorophenylacetonitrile, 0. 22 g (1 mmol) of palladium acetate, 2 · 2g (4mmol) 2,2 bis(dicyclohexyl)_1,1'-biphenyl (DCPB) and 12.74g(60 mmol) potassium phosphate was added to the reaction flask, and 200 ml of dioxane was added thereto, and the mixture was heated to 80 ° C for 24 hours. After completion of the reaction, it was washed with water and methanol, and purified by column chromatography to afford 6.48 g (8.4 mmol) The yield was 84%.

Reference： [1]Current Patent Assignee: CHANGCHUN HAIPU RUNSI TECHNOLOGY CO LTD - CN108329245, 2018, A Location in patent: Paragraph 0064-0065; 0068

72
[ 653-30-5 ]
[ 96159-17-0 ]
C₃₆H₁₆F₁₀N₄ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
31%	With pyridine; titanium tetrachloride In dichloromethane for 24h; Cooling with ice;	1 In the ice water bath,Intermediate S1 (5.48 g, 17.34 mmol) and compound F1-2 (16.37 g, 79.03 mmol) were added to a 250 ml flask.Titanium tetrachloride (29.98 g, 158.05 mmol), pyridine (12.5 g, 158.05 mmol) and dichloromethane (100 ml),Stir at low temperature for 24 hours.After the reaction, water was added to the flask, and the organic phase was extracted with dichloromethane, and the organic phase was concentrated.Column chromatography was carried out with a mixed solution of ethyl acetate and hexane, and the crude product was recrystallized from dichloromethane and petroleum ether.Filtration gave Compound I-1 (3.73 g, 31%).

Reference： [1]Current Patent Assignee: CHANGCHUN HAIPU RUNSI TECHNOLOGY CO LTD - CN108329286, 2018, A Location in patent: Paragraph 0096; 0097; 0099

73
[ 615-93-0 ]
[ 653-30-5 ]
C₂₂H₂Cl₂F₁₀N₂ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
74%	With pyridine; titanium tetrachloride In dichloromethane for 24h;	1 Preparation of intermediate M-1:8.85 g (50 mmol) of 2,5-dichloro-p-benzoquinone,47.63 g (230 mmol) of 2,3,4,5,6-pentafluorophenylacetonitrile,86.3 g (455 mmol) of titanium tetrachloride was added to the reaction flask.Add 36 ml (455 mmol) of pyridine and290 ml of dichloromethane,Reaction for 24 hours, suction filtration,The filtrate is subjected to distillation under reduced pressure to remove the organic solvent.Purified by silica gel column with ethyl acetate / cyclohexane as eluent.Finally, it is recrystallized from a mixed solution of dichloromethane/petroleum ether.Yielding 20.54 g (37 mmol) of intermediate M-1,The yield was 74%.

Reference： [1]Current Patent Assignee: CHANGCHUN HAIPU RUNSI TECHNOLOGY CO LTD - CN108373425, 2018, A Location in patent: Paragraph 0043

74
[ 653-30-5 ]
C₂₂H₂Cl₂F₁₀N₂ [ No CAS ]
C₃₈H₄F₂₀N₄ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
77%	With potassium phosphate; dicyclohexyl-({2-[2-(dicyclohexylphosphanyl)phenyl]-phenyl})-phosphane; palladium diacetate In 1,4-dioxane at 80℃; for 24h;	2 Preparation of Compound HT1 5.55 g (10 mmol) of intermediate M-1,6.21 g (30 mmol) of 2,3,4,5,6-pentafluorophenylacetonitrile,0.22 g (1 mmol) of palladium acetate,2.2 g (4 mmol) of 2,2'-bis(dicyclohexyl)-1,1'-biphenyl (DCPB)And 12.74g (60mmol) potassium phosphate addedInto the reaction bottle,Add 200ml of dioxane,Heat to 80 ° C,Reaction for 24 hours.After the reaction is finished, suction filtration,The obtained filtrate was subjected to distillation under reduced pressure to remove the solvent.Then wash with water and methanol,Purified by column chromatography,6.9 g (7.7 mmol) of compound HT1 were obtained.The yield was 77%.

Reference： [1]Current Patent Assignee: CHANGCHUN HAIPU RUNSI TECHNOLOGY CO LTD - CN108373425, 2018, A Location in patent: Paragraph 0045; 0046

75
[ 653-30-5 ]
[ 7003-69-2 ]
C₄₁H₁₂F₁₅N₃ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
59%	With pyridine; titanium tetrachloride In dichloromethane for 24h;	2 Example 2: Preparation of Compound HT1 1.32 g (5 mmol) of compound M-1, 7.14 g (34.5 mmol)2,3,4,5,6-pentafluorophenylacetonitrile,12.8g (67.5mmol) of titanium tetrachloride was added to the reaction flask.Add 5.4 ml (67.5 mmol) of pyridine and 44 ml of dichloromethane.Reaction for 24 hours,Filtering,The filtrate is subjected to distillation under reduced pressure to remove the organic solvent.Then use ethyl acetate / cyclohexane over silica gel column,Finally, it is recrystallized from a mixed solution of dichloromethane and petroleum ether.2.45 g (2.95 mmol) of compound HT1 was obtained in a yield of 59%.

Reference： [1]Current Patent Assignee: CHANGCHUN HAIPU RUNSI TECHNOLOGY CO LTD - CN108373428, 2018, A Location in patent: Paragraph 0050; 0051

76
[ 653-30-5 ]
C₁₀Cl₂N₄O [ No CAS ]
C₂₆H₄F₁₀N₆O [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
86%	With potassium phosphate; 2,6-bis(4-carboxyphenoxy)benzonitrile; palladium diacetate In 1,4-dioxane at 80℃; for 24h; Inert atmosphere;	1 Under argon protection,Compound D1 (1.31 g, 5 mmol) was added to the flask.Pentafluorophenylacetonitrile (2.07 g, 10 mmol), palladium acetate (0.11 g, 0.5 mmol),2,6-bis(4-carboxyphenoxy)benzonitrile (0.38 g, 1 mmol),Potassium phosphate (6.37 g, 30 mmol) and dioxane (50 ml),Stir at 80 ° C for 24 hours.After the reaction was completed, it was cooled to room temperature, and the mixture was filtered.The filtrate was concentrated under reduced pressure.The crude product was subjected to column chromatography to yield Compound E1 (2.61 g, 86%).

Reference： [1]Current Patent Assignee: CHANGCHUN HAIPU RUNSI TECHNOLOGY CO LTD - CN108752296, 2018, A Location in patent: Paragraph 0080; 0084-0085

77
[ 653-30-5 ]
C₂₁H₁₂N₂O₂ [ No CAS ]
C₂₉H₁₂F₅N₃O [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
57%	With sodium ethanolate In ethanol Heating;	1 9.73 g (30 mmol) of intermediate D-1, 7.45 g (35.99 mmol)2-(perfluorophenyl)acetonitrile and 6.12 g (90 mmol) sodium ethoxide were dissolved in 100 ml of ethanol.Then, the mixture was heated and stirred, and the reaction mixture was concentrated, and the residue was diluted with tetrahydrofuran, and washed with water and brine.The organic layer was collected, dried over anhydrous magnesium sulfate, and the organic solvent was removed by distillation under reduced pressure, and finally purified by silica gel column chromatography.8.78 g (17.1 mmol) of Compound 1 was obtained in a yield of 57%.

Reference： [1]Current Patent Assignee: CHANGCHUN HAIPU RUNSI TECHNOLOGY CO LTD - CN108976177, 2018, A Location in patent: Paragraph 0074; 0075; 0080

78
[ 653-30-5 ]
[ 3096-56-8 ]
C₄₂H₂₅F₅N₂ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 2 steps 1: sodium ethanolate / ethanol 2: tetrakis(triphenylphosphine) palladium⁽⁰⁾; sodium carbonate / toluene; ethanol; water / 2 h / 90 °C

Reference： [1]Current Patent Assignee: CHANGCHUN HAIPU RUNSI TECHNOLOGY CO LTD - CN109134369, 2019, A

79
[ 653-30-5 ]
[ 3096-56-8 ]
C₂₁H₇BrF₅N [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
75%	With sodium ethanolate In ethanol Heating;	1 Example 1: Preparation of Compound 1 Compound 1-1 (5.16 g, 20 mmol), 1-2 (4.14 g, 20 mmol) and sodium ethoxide were completely dissolved in 100 ml of ethanol in a round bottom flask, and then the resulting solution was heated and stirred. After completion of the reaction, the residue obtained by concentrating the obtained product under reduced pressure was diluted with tetrahydrofuran and washed with water and brine. The organic solvent layer was collected, water was evaporated over anhydrous magnesium sulfate, and the residue was filtered and evaporated. The concentrated solution was purified by silica gel column chromatography to give compound 6.70 g of Compound 1-3.The yield was 75%.
75%	With sodium ethanolate In ethanol Heating;	1 Compound 1-1 (5.16 g, 20 mmol) in a round bottom flask,1-2 (4.14g, 20mmol) and sodium ethoxide were completely dissolved in 100ml of ethanol,The resulting solution was then heated and stirred.After the reaction is over,The residue obtained by concentrating the obtained product under reduced pressure was diluted with tetrahydrofuran,Wash with water and brine. The organic solvent layer was collected, water was evaporated over anhydrous magnesium sulfate, and the residue was filtered and evaporated.The concentrated solution was purified by silica gel column chromatography to give compound 6.70 g of Compound 1-3.The yield was 75%.
60%	With sodium ethanolate In ethanol	8 Compound b (2.50 g, 8.92 mmol) in a 250 ml round bottom flask,Compound p (2.22 g, 10.70 mmol) and sodium ethoxide (1.82 g, 26.76 mmol) were completely dissolved in 30 ml of ethanol, and then the resulting solution was heated and stirred.After completion of the reaction, the residue obtained by concentrating the obtained product under reduced pressure was diluted with tetrahydrofuran and washed with water and brine. Collecting organic solvent layers,The water was removed with anhydrous magnesium sulfate, and the residue was filtered and evaporated.The concentrated solution was purified by silica gel column chromatography (Hex: EA = 1:1) to yield compound t (2.40 g, 60%).

56%

With sodium ethanolate In ethanol Inert atmosphere; Heating;

2.3 Step3: Under nitrogen protection,2-bromo-9-fluorenone (2.59 g, 10 mmol) was added to the reactor.Intermediate A-2-2 (2.49 g, 12 mmol)And sodium ethoxide (2.04g, 30mmol)Completely dissolved in 30ml of ethanol,The resulting solution was then heated and stirred.After the reaction is over,The residue obtained by concentrating the obtained product under reduced pressure was diluted with tetrahydrofuran,Wash with water and brine.Collecting organic solvent layers,Removing water by anhydrous magnesium sulfate,Filter the residue,It was then concentrated under reduced pressure.The solution was concentrated to give intermediate A-2-3 was purified by silica gel column chromatography (2.51g, 56%).

Reference： [1]Current Patent Assignee: CHANGCHUN HAIPU RUNSI TECHNOLOGY CO LTD - CN109265438, 2019, A Location in patent: Paragraph 0071-0073
[2]Current Patent Assignee: CHANGCHUN HAIPU RUNSI TECHNOLOGY CO LTD - CN109320493, 2019, A Location in patent: Paragraph 0077; 0078; 0079
[3]Current Patent Assignee: CHANGCHUN HAIPU RUNSI TECHNOLOGY CO LTD - CN109134369, 2019, A Location in patent: Paragraph 0135; 0136; 0137
[4]Current Patent Assignee: CHANGCHUN HAIPU RUNSI TECHNOLOGY CO LTD - CN109134311, 2019, A Location in patent: Paragraph 0090; 0091; 0094

80
[ 653-30-5 ]
C₃₈H₂₀F₅N [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 2 steps 1: sodium ethanolate / ethanol / Inert atmosphere; Heating 2: tetrakis(triphenylphosphine) palladium⁽⁰⁾; sodium carbonate / ethanol; toluene; water / 3 h / Inert atmosphere; Reflux

Reference： [1]Current Patent Assignee: CHANGCHUN HAIPU RUNSI TECHNOLOGY CO LTD - CN109134311, 2019, A

81
[ 653-30-5 ]
C₅₅H₃₂F₅N [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 2 steps 1: sodium ethanolate / ethanol / Inert atmosphere; Heating 2: tetrakis(triphenylphosphine) palladium⁽⁰⁾; sodium carbonate / ethanol; toluene; water / 3 h / Inert atmosphere; Reflux

Reference： [1]Current Patent Assignee: CHANGCHUN HAIPU RUNSI TECHNOLOGY CO LTD - CN109134311, 2019, A

82
[ 653-30-5 ]
[ 14348-75-5 ]
C₂₁H₆Br₂F₅N [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
56%	With sodium ethanolate In ethanol Inert atmosphere; Heating;	5.1 Step1: Under nitrogen protection,2,7-dibromo-9-fluorenone (3.38 g, 10 mmol) was added to the reactor.Intermediate A-2-2 (2.49 g, 12 mmol)And sodium ethoxide (2.04g, 30mmol)Completely dissolved in 30ml of ethanol,The resulting solution was then heated and stirred.After the reaction is over,The residue obtained by concentrating the obtained product under reduced pressure was diluted with tetrahydrofuran,Wash with water and brine.Collecting organic solvent layers,Removing water by anhydrous magnesium sulfate,Filter the residue,It was then concentrated under reduced pressure.The concentrated solution was purified by silica gel column chromatography to give an intermediateA-152-1 (2.95 g, 56%).

Reference： [1]Current Patent Assignee: CHANGCHUN HAIPU RUNSI TECHNOLOGY CO LTD - CN109134311, 2019, A Location in patent: Paragraph 0113; 0114; 0115

83
[ 109-99-9 ]
[ 653-30-5 ]
2-(2,3,5,6-tetrafluoro-4-(tetrahydrofuran-2-yl)phenyl)acetonitrile [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
45%	With Quinuclidine; dipotassium hydrogenphosphate; 2,2′-bipyridylbis[2-(2′,4′-difluorophenyl)pyridine]iridium(III) hexafluorophosphate at -78℃; for 72h; Inert atmosphere; Sealed tube; Irradiation;

Reference： [1]Wang, Junlei; Huang, Binbin; Gao, Yuan; Yang, Chao; Xia, Wujiong [Journal of Organic Chemistry, 2019, vol. 84, # 11, p. 6895 - 6903]

84
[ 653-30-5 ]
[ 1580-18-3 ]
C₃₀F₁₈N₂ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
62%	With potassium carbonate In tetrahydrofuran at 20℃; for 4h;	12 Synthesis of compound C11 Add M5 (35.20 g, 1 equivalent) to a 250 ml single-necked flask,Compound N8 (20.70 g, 1 equivalent), potassium carbonate (28.98 g, 2.10 equivalents),150 ml of tetrahydrofuran was stirred at room temperature for 4 hours. The solvent was spin-dried to obtain the crude product.The crude product was purified by chromatography (ethyl acetate / hexane volume ratio 1/8),Compound C11(45.26 g, 62%).

Reference： [1]Current Patent Assignee: NINGBO LUMILAN NEW MATERIAL CO LTD - CN110437103, 2019, A Location in patent: Paragraph 0167-0174

85
[ 653-30-5 ]
[ 1211417-77-4 ]
C₁₃H₁₂BF₄N₃ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With dipotassium hydrogenphosphate; (4,4'-di-tert-butyl-2,2'-dipyridyl)-bis-(2-phenylpyridine(-1H))-iridium(III) hexafluorophosphate at 20℃; for 48h; Schlenk technique; Inert atmosphere; Irradiation; Sealed tube; regioselective reaction;

Reference： [1]Chen, Kai; Chen, Xiao-Qing; Hu, Yuan-Zhuo; Xia, Peng-Ju; Xiang, Hao-Yue; Xiao, Jun-An; Yang, Hua; Ye, Zhi-Peng [Organic Letters, 2020, vol. 22, # 5, p. 1742 - 1747]

86
[ 653-30-5 ]
C₂₄H₉N₃O₂ [ No CAS ]
C₄₀H₉F₁₀N₅ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
32%	With dmap; titanium tetrachloride In toluene for 6h; Inert atmosphere; Reflux;	13 Synthesis Example 13: Synthesis of Compound 13 Intermediate compound 13-1 (3.71g, 10mmol) and pentafluorobenzyl cyanide (16.56g, 80mmol) were added to a 100ml three-necked flask, then 50ml of anhydrous toluene was added, and DMAP (9.7g, 80mmol) was added under nitrogen protection React with titanium tetrachloride (12.4g, 60mmol) under reflux for 6 hours, cool, pour the reaction liquid into water, concentrate to remove toluene, EA and water liquid, combine the organic phases, concentrate, EA and PE are purified by column to obtain a pale yellow solid 2.39g, yield=32%.

Reference： [1]Current Patent Assignee: Yang Xi - CN111253396, 2020, A Location in patent: Paragraph 0113-0115

87
[ 653-30-5 ]
C₂₄H₆F₁₂I₂N₂ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 2 steps 1.1: lithium hydride / tetrahydrofuran / 0.5 h / 0 - 20 °C 1.2: 15 h / 0 - 25 °C / Cooling with ice 2.1: n-butyllithium / tetrahydrofuran / 1.75 h / -78 - 20 °C 2.2: -78 °C

Reference： [1]Current Patent Assignee: JILIN OLED OPTICAL AND ELECTRONIC MATERIALS CO LTD - CN111718280, 2020, A

88
[ 653-30-5 ]
C₂₈H₈F₁₂N₆O₄ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 3 steps 1.1: lithium hydride / tetrahydrofuran / 0.5 h / 0 - 20 °C 1.2: 15 h / 0 - 25 °C / Cooling with ice 2.1: n-butyllithium / tetrahydrofuran / 1.75 h / -78 - 20 °C 2.2: -78 °C 3.1: lithium hydride / tetrahydrofuran / 0.5 h / 0 - 20 °C 3.2: 15 h / 0 - 25 °C

Reference： [1]Current Patent Assignee: JILIN OLED OPTICAL AND ELECTRONIC MATERIALS CO LTD - CN111718280, 2020, A

89
[ 653-30-5 ]
C₂₈F₁₂N₆O₄ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 4 steps 1.1: lithium hydride / tetrahydrofuran / 0.5 h / 0 - 20 °C 1.2: 15 h / 0 - 25 °C / Cooling with ice 2.1: n-butyllithium / tetrahydrofuran / 1.75 h / -78 - 20 °C 2.2: -78 °C 3.1: lithium hydride / tetrahydrofuran / 0.5 h / 0 - 20 °C 3.2: 15 h / 0 - 25 °C 4.1: bis-[(trifluoroacetoxy)iodo]benzene / tetrahydrofuran / 12 h / 20 °C

Reference： [1]Current Patent Assignee: JILIN OLED OPTICAL AND ELECTRONIC MATERIALS CO LTD - CN111718280, 2020, A

90
[ 653-30-5 ]
C₈H₆Br₂F₂ [ No CAS ]
C₂₄H₈F₁₂N₂ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
85%	Stage #1: (pentafluorophenyl)acetonitrile With lithium hydride In tetrahydrofuran at 0 - 20℃; for 0.5h; Stage #2: C₈H₆Br₂F₂ In tetrahydrofuran at 0 - 25℃; for 15h; Cooling with ice;	3 Lithium hydride (176mmol) was added to tetrahydrofuran (176mL) and cooled to 0°C, the reactant b-50 (176mmol) was dissolved in a small amount (176mL) of THF, and it was slowly added dropwise to the lithium hydride solution at 0°C In the process, the cooling device was removed and the temperature was raised to room temperature, reacted at room temperature for 30 minutes, and then cooled to 0°C; the reactant a-50 (80 mmol) (80 mL) THF solution was added dropwise, and the reaction was carried out at 25°C for 15 hours. The reaction was poured into ice water, the pH was adjusted to 1.0 with concentrated hydrochloric acid, extracted three times with ethyl acetate, the organic phases were combined, washed with saturated brine, water, and aqueous sodium bicarbonate in turn, dried over sodium sulfate, and the solvent was removed to the intermediate c-50 (37.5g, yield: 85%)

Reference： [1]Current Patent Assignee: JILIN OLED OPTICAL AND ELECTRONIC MATERIALS CO LTD - CN111718280, 2020, A Location in patent: Paragraph 0057-0059

91
[ 653-30-5 ]
C₁₂H₃Br₃N₁₀ [ No CAS ]
C₃₆H₆F₁₅N₁₃ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
79.4%	Stage #1: C₁₂H₃Br₃N₁₀ With sodium hydride In tetrahydrofuran at 0℃; for 1h; Inert atmosphere; Stage #2: (pentafluorophenyl)acetonitrile With tetrakis(triphenylphosphine) palladium⁽⁰⁾ In tetrahydrofuran at 70℃; for 10.5h; Inert atmosphere;	2.S3 S3. Dissolve Intermediate D-6 (70mmol) in THF (350ml),Protected with nitrogen, fully cooled to 0,Slowly add sodium hydride (210mmol) in batches with stirring,React at 0°C for 1h. Add E-6 (210mmol) and tetrakistriphenylphosphine palladium (10.5mmol) under nitrogen atmosphere. After half an hour,The mixture was heated to 70°C for 10 hours.Remove the solvent and add hydrochloric acid (2N) to adjust the pH to 1,The precipitated solid was filtered with suction, washed with water and ethanol, and dried to obtain intermediate F-6 (50.30g, yield 79.4%,

Reference： [1]Current Patent Assignee: JILIN OLED OPTICAL AND ELECTRONIC MATERIALS CO LTD - CN111848635, 2020, A Location in patent: Paragraph 0052-0054; 0058

92
[ 653-30-5 ]
C₈H₂BrN₃O [ No CAS ]
C₁₆H₂BrF₅N₄ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
60.5%	With pyridine; titanium tetrachloride In dichloromethane for 25h; Cooling with ice;	4.1 (1) Compound 15-1 The compound 4-2 (10 g, 0.042 mol), (pentafluorophenyl)acetonitrile (12.3 g, 0.059 mol) and methylene chloride (400 ml) were put into a flask and cooled in anice-bath. TiCl4(11.2 g, 0.059 mol) was slowly dropped, and pyridine (10.5 g, 0.127 mol) was very slowly added. After 1 hr, theice-bathwas removed. The mixture was stirred and reacted for 24 hrs. After completion of reaction, the resultant was extracted using hydrochloric acid aqueous solution and column-refined to obtain the compound 15-1. (10.9 g, yield=60.5%)

Reference： [1]Current Patent Assignee: P&H TECH CO.,LTD.; LG DISPLAY CO.,LTD. - US2021/50527, 2021, A1 Location in patent: Paragraph 0093-0095

93
[ 653-30-5 ]
C₁₂HF₇INOS [ No CAS ]
C₂₀F₁₂N₂OS [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
80%	With 2-Picolinic acid; copper(l) iodide; titanium(IV)isopropoxide; caesium carbonate In dichloromethane at 40℃; for 1h;	2.2 (2) Synthesis of Intermediate 2-3 Under anhydrous and oxygen-free conditions, add Intermediate 2-2 (1mmol), pentafluorobenzyl cyanide (1mmol), CuI (1mmol), 2-picolinic acid (2mmol), and cesium carbonate (3.5mmol) in a 100mL three-necked flask. , Add 20mL of anhydrous 1,4-dioxane with a syringe, add tetraisopropyl titanate (3mmol) with a syringe, stir and react at 40°C for 1h. The reaction solution was poured into 200 mL of saturated brine, extracted three times with EA, the organic phases were combined, washed three times with 50 mL of water, dried over anhydrous magnesium sulfate, concentrated under reduced pressure and mixed, separated by column chromatography, and eluted with ethyl acetate/petroleum ether to obtain 453 mg Intermediate 2-3, the yield is 80%.

Reference： [1]Current Patent Assignee: TCL TECHNOLOGY GROUP CORPORATION - CN112552223, 2021, A Location in patent: Paragraph 0182-0184; 0187-0188

94
[ 653-30-5 ]
C₃H₃I₃S [ No CAS ]
C₂₇F₁₅N₃S [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
84%	With 2-Picolinic acid; copper(l) iodide; titanium(IV)isopropoxide; caesium carbonate In 1,4-dioxane at 40℃; for 1h;	3.1 (1) Synthesis of Intermediate 3-2 Under anhydrous and oxygen-free conditions, Intermediate 3-1 (1mmol), pentafluorobenzyl cyanide (3mmol), CuI (1mmol), 2-picolinic acid (2mmol), and cesium carbonate (5mmol) were sequentially added to a 100mL three-necked flask under anhydrous and oxygen-free conditions. Add 20 mL of anhydrous 1,4-dioxane with a syringe, add tetraisopropyl titanate (3 mmol) with a syringe, and stir for 1 hour at 40°C. The reaction solution was poured into 200 mL of saturated brine, extracted three times with EA, the organic phases were combined, washed three times with 50 mL of water, dried over anhydrous magnesium sulfate, concentrated under reduced pressure and mixed, separated by column chromatography, and eluted with ethyl acetate/petroleum ether to obtain 573 mg Intermediate 3-2, the yield was 84%.

Reference： [1]Current Patent Assignee: TCL TECHNOLOGY GROUP CORPORATION - CN112552223, 2021, A Location in patent: Paragraph 0192-0195

95
[ 653-30-5 ]
C₆H₄I₂N₂S₂ [ No CAS ]
C₂₂H₂F₁₀N₄S₂ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
18%	With 2-Picolinic acid; copper(l) iodide; titanium(IV)isopropoxide; caesium carbonate In 1,4-dioxane at 40℃; for 1h;	10.1 (1) Synthesis of Intermediate 10-2 Under anhydrous and oxygen-free conditions,Into a 100mL three-necked flask was added compound 10-1 (1mmol) in sequence,Pentafluorobenzyl cyanide (2mmol), CuI (1mmol),2-picolinic acid (2mmol), cesium carbonate (3.5mmol),Add 20 mL of anhydrous 1,4-dioxane with a syringe,Add tetraisopropyl titanate (3mmol) with a syringe,The reaction was stirred at 40°C for 1 h. Pour the reaction solution into 200mL saturated saline,EA was extracted three times, the organic phases were combined, and washed three times with 50 mL of water,Dry with anhydrous magnesium sulfate, concentrate under reduced pressure, mix the sample,Column chromatography separation, ethyl acetate/petroleum ether elution,103 mg of Intermediate 10-2 was obtained,The yield was 18%.

Reference： [1]Current Patent Assignee: TCL TECHNOLOGY GROUP CORPORATION - CN112552223, 2021, A Location in patent: Paragraph 0245-0248

96
[ 653-30-5 ]
C₁₄N₈O₂ [ No CAS ]
C₃₀F₁₀N₁₀ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
6.9 g	With aluminum oxide In toluene at 20℃; for 4h;	1.2 (2) Synthesis of compound P1: 500 three-necked flask, add M-1 (7.8g, 0.025mol), add 200ml of toluene and stir to completely dissolve, add 5-fluorobenzene acetonitrile (5.2g, 0.025mol), add neutral alumina (6.4g, 0.063 mol), react at room temperature for 4 hours, complete the reaction, filter, and recrystallize the crude solid product with a mixed solvent of tetrahydrofuran and n-heptane to obtain P1 (6.9 g, 0.01 mol).

Reference： [1]Current Patent Assignee: BEIJING SINEVA TECHNOLOGY CO LTD - CN112679503, 2021, A Location in patent: Paragraph 0034-0036; 0040-0043

97
[ 653-30-5 ]
3-(4-chlorophenyl)-1-[2-(2, 3,4,5, 6-pentafluorophenyl)ethyl]urea [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 2 steps 1: lithium aluminium tetrahydride; aluminum (III) chloride / tetrahydrofuran / 1 h / 20 °C 2: chloroform / 16 h / 60 °C

Reference： [1]Nguyen, Thuy; Gamage, Thomas F.; Finlay, David B.; Decker, Ann M.; Langston, Tiffany L.; Barrus, Daniel; Glass, Michelle; Li, Jun-Xu; Kenakin, Terry P.; Zhang, Yanan [Journal of Medicinal Chemistry, 2022, vol. 65, # 1, p. 257 - 270]

98
[ 653-30-5 ]
[ 53001-67-5 ]

Yield	Reaction Conditions	Operation in experiment
35 %Chromat.	With phenylsilane; 2-H-1,3-di-tert-butyl-2,3-dihydro-1H-1,3,2-diazaphosphole In acetonitrile at 100℃; for 12h; Inert atmosphere; Schlenk technique;

Reference： [1]Zhang, Jingjing; Zhao, Xiao; Yang, Jin-Dong; Cheng, Jin-Pei [Journal of Organic Chemistry, 2022, vol. 87, # 1, p. 294 - 300]

99
[ 653-30-5 ]
C₂₂H₁₄O₂ [ No CAS ]
C₃₈H₁₄F₁₀N₂ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
54%	With pyridine; titanium(IV) tetrachloride In chloroform for 24h; Reflux; Inert atmosphere;	6 Synthesis of Compound HI-6 Intermediate 26 (1 mmol) and compound 27 (3.5 mmol) were dissolved in 50 mL of anhydrous chloroform, then 4 mL of titanium tetrachloride and 4 mL of pyridine were added, and the reaction was stirred and refluxed under nitrogen protection for 24 h. Filtration to obtain compound HI-6 with a yield of 54%.

Reference： [1]Current Patent Assignee: GUANGZHOU CORE PHOTOELECTRIC MAT - CN114163300, 2022, A Location in patent: Paragraph 0203-0204; 0209-0210

100
[ 653-30-5 ]
C₂₂H₈F₄O₄ [ No CAS ]
C₃₈H₈F₁₄N₂O₂ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
44%	With pyridine; titanium(IV) tetrachloride In chloroform for 24h; Inert atmosphere; Reflux;	11 Synthesis of Compound HI-11 Intermediate 44 (1 mmol) and compound 27 (3.5 mmol) were dissolved in 50 mL of anhydrous chloroform, then 4 mL of titanium tetrachloride and 4 mL of pyridine were added, and the reaction was stirred and refluxed under nitrogen protection for 24 h. Filtration to obtain compound HI-11 with a yield of 44%.

Reference： [1]Current Patent Assignee: GUANGZHOU CORE PHOTOELECTRIC MAT - CN114163300, 2022, A Location in patent: Paragraph 0245-0246; 0251-0252

101
[ 653-30-5 ]
6,7-dioxo-5,6,7,8-tetrahydropyrazino-[2,3-b]pyrazine-2,3-dicarbonitrile [ No CAS ]
C₂₄F₁₀N₈ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
49%	With pyridine; titanium(IV) tetrachloride In dichloromethane for 24h; Inert atmosphere; Reflux;	7 Synthesis of compound 7: Compound titanium tetrachloride (4.67 g, 25 mmol), 7-2 (10 mmol) 7-3 (20 mmol),Dry pyridine/dichloromethane under nitrogen as solvent and reflux for 24 hours,Then quenched with cold concentrated hydrochloric acid, concentrated with dichloromethane, then dried with anhydrous sodium sulfate, distilled under reduced pressure,The residue was recrystallized from DCM/MeOH to give compound 7 (4.9 mmol) in 49% yield,

Reference： [1]Current Patent Assignee: GUANGZHOU CHINARAY OPTOELECTRONIC MATERIALS LTD. - CN114369068, 2022, A Location in patent: Paragraph 0174-0175; 0178-0179

102
[ 653-30-5 ]
C₁₈H₄Br₂N₆ [ No CAS ]
C₃₂H₈F₁₀N₆ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
69.3%	Stage #1: 2,3,4,5,6-pentafluorophenylacetonitrile With sodium tertiary butoxide In tetrahydrofuran for 0.25h; Inert atmosphere; Stage #2: C₁₈H₄Br₂N₆ With copper (I) iodide; tetrakis-(triphenylphosphine)-palladium In tetrahydrofuran at 60℃; for 12h; Inert atmosphere;	10 Synthesis of compound DPI-10: Sodium tert-butoxide (50mmol) and A26 (40mmol) were stirred for 15min under nitrogen, dry tetrahydrofuran, and A25 (10mmol), Pd(PPh3)4 (6.8g, 6mmol), cuprous iodide were added at room temperature (7.8 g, 40 mmol) and then stirred at 60 degrees for 12 hours, then quenched with cold concentrated hydrochloric acid, concentrated with dichloromethane, then dried over anhydrous sodium sulfate, distilled under reduced pressure, the residue was recrystallized from DCM/MeOH, and used Glacial acetic acid dissolves the recrystallized product, then cools to 0 degrees, then adds a mixture of nitric acid and hydrobromic acid, stirs at room temperature after the addition is complete, uses distilled water to quench the reaction, and continues to stir after solid precipitation, and then obtains an orange solid to obtain DPI -10 (6.93 mmol, 69.3%)

Reference： [1]Current Patent Assignee: GUANGZHOU CHINARAY OPTOELECTRONIC MATERIALS LTD. - CN114573587, 2022, A Location in patent: Paragraph 0196-0197; 0200-0201

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Technical Information

• Acidity of Phenols • Acids Combine with Acyl Halides to Produce Anhydrides • Acyl Chloride Hydrolysis • Add Hydrogen Cyanide to Aldehydes and Ketones to Produce Alcohols • Alkyl Halide Occurrence • Amide Hydrolysis • Amide Hydrolysis • Amine Synthesis from Nitriles • Amine Synthesis from Nitriles • An Alkane are Prepared from an Haloalkane • Anhydride Hydrolysis • Arndt-Eistert Homologation • Benzylic Oxidation • Birch Reduction • Birch Reduction of Benzene • Blaise Reaction • Blanc Chloromethylation • Carbonation of Organometallics • Carboxylate Salt Formation • Carboxylic Acids React with Alcohols to Form Esters • Catalytic Hydrogenation • Chan-Lam Coupling Reaction • Complete Benzylic Oxidations of Alkyl Chains • Complete Benzylic Oxidations of Alkyl Chains • Complex Metal Hydride Reductions • Conjugate Additions of p-Benzoquinones • Conversion of Amino with Nitro • Cyanohydrins can be Convert to Carbonyl Compounds under Basic Conditions • Decarboxylation of Substituted Propanedioic • Decomposition of Arenediazonium Salts to Give Phenols • Deprotection of Cbz-Amino Acids • Deprotonation of Methylbenzene • Diazo Coupling • DIBAL Attack Nitriles to Give Ketones • Directing Electron-Donating Effects of Alkyl • Electrophilic Chloromethylation of Polystyrene • Electrophilic Substitution of the Phenol Aromatic Ring • Esters Hydrolyze to Carboxylic Acids and Alcohols • Etherification Reaction of Phenolic Hydroxyl Group • Formation of an Amide from an Amine and a Carboxylic Acid • Formation of an Amide from an Amine and a Carboxylic Acid • Friedel-Crafts Alkylation of Benzene with Acyl Chlorides • Friedel-Crafts Alkylation of Benzene with Carboxylic Anhydrides • Friedel-Crafts Alkylation of Benzene with Haloalkanes • Friedel-Crafts Alkylation Using Alkenes • Friedel-Crafts Alkylations of Benzene Using Alkenes • Friedel-Crafts Alkylations Using Alcohols • Friedel-Crafts Reaction • Groups that Withdraw Electrons Inductively Are Deactivating and Meta Directing • Halogenation of Benzene • Halogenation of Phenols • Hunsdiecker-Borodin Reaction • Hydride Reductions • Hydrogenation to Cyclohexane • Hydrogenolysis of Benzyl Ether • Ketone Synthesis from Nitriles • Kolbe-Schmitt Reaction • Nitration of Benzene • Nitriles Hydrolyze to Carboxylic Acids • Nucleophilic Aromatic Substitution • Nucleophilic Aromatic Substitution with Amine • Oxidation of Aldehydes Furnishes Carboxylic Acids • Oxidation of Alkyl-substituted Benzenes Gives Aromatic Ketones • Oxidation of Phenols • Oxidation of Primary Alcohols Furnishes Carboxylic Acids • Passerini Reaction • Pechmann Coumarin Synthesis • Peptide Bond Formation with DCC • Periodic Acid Degradation of Sugars • Preparation of Aldehydes and Ketones • Preparation of Alkylbenzene • Preparation of Amines • Preparation of Carboxylic Acids • Reactions of Amines • Reactions of Benzene and Substituted Benzenes • Reactions of Carboxylic Acids • Reduction of Carboxylic Acids by LiAlH4 • Reduction of Carboxylic Acids by Lithium Aluminum Hydride • Reduction of Carboxylic Acids by Lithium Aluminum Hydride • Reductive Removal of a Diazonium Group • Reimer-Tiemann Reaction • Reverse Sulfonation——Hydrolysis • Ritter Reaction • Schmidt Reaction • Specialized Acylation Reagents-Ketenes • Sulfonation of Benzene • The Acylium Ion Attack Benzene to Form Phenyl Ketones • The Claisen Rearrangement • The Conversion of Carboxylic Acids into Acyl Halides • The Cycloaddition of Dienes to Alkenes Gives Cyclohexenes • The Nitro Group Conver to the Amino Function • Thorpe-Ziegler Reaction • Ugi Reaction • Vilsmeier-Haack Reaction

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H271	May cause fire or explosion; strong oxidizer
H272	May intensify fire; oxidizer
H280	Contains gas under pressure; may explode if heated
H281	Contains refrigerated gas; may cause cryogenic burns or injury
H290	May be corrosive to metals
Health hazards
Code	Phrase
H300	Fatal if swallowed
H301	Toxic if swallowed
H302	Harmful if swallowed
H303	May be harmful if swallowed
H304	May be fatal if swallowed and enters airways
H305	May be harmful if swallowed and enters airways
H310	Fatal in contact with skin
H311	Toxic in contact with skin
H312	Harmful in contact with skin
H313	May be harmful in contact with skin
H314	Causes severe skin burns and eye damage
H315	Causes skin irritation
H316	Causes mild skin irritation
H317	May cause an allergic skin reaction
H318	Causes serious eye damage
H319	Causes serious eye irritation
H320	Causes eye irritation
H330	Fatal if inhaled
H331	Toxic if inhaled
H332	Harmful if inhaled
H333	May be harmful if inhaled
H334	May cause allergy or asthma symptoms or breathing difficulties if inhaled
H335	May cause respiratory irritation
H336	May cause drowsiness or dizziness
H340	May cause genetic defects
H341	Suspected of causing genetic defects
H350	May cause cancer
H351	Suspected of causing cancer
H360	May damage fertility or the unborn child
H361	Suspected of damaging fertility or the unborn child
H361d	Suspected of damaging the unborn child
H362	May cause harm to breast-fed children
H370	Causes damage to organs
H371	May cause damage to organs
H372	Causes damage to organs through prolonged or repeated exposure
H373	May cause damage to organs through prolonged or repeated exposure
Environmental hazards
Code	Phrase
H400	Very toxic to aquatic life
H401	Toxic to aquatic life
H402	Harmful to aquatic life
H410	Very toxic to aquatic life with long-lasting effects
H411	Toxic to aquatic life with long-lasting effects
H412	Harmful to aquatic life with long-lasting effects
H413	May cause long-lasting harmful effects to aquatic life
H420	Harms public health and the environment by destroying ozone in the upper atmosphere

[ CAS No. 653-30-5 ] {[proInfo.proName]}

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[ 653-30-5 ] Synthesis Path-Downstream 1~102

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Fluorinated Building Blocks

Aryls

Nitriles

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[ 653-30-5 ]