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ChemicalBook CAS DataBase List methyl 5-cyano-2-(trifluoromethyl)benzoate
1415089-89-2

methyl 5-cyano-2-(trifluoromethyl)benzoate synthesis

2synthesis methods
5-Chloro-2-(trifluoromethyl)benzoic acid methyl ester

521064-74-4
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methyl 5-cyano-2-(trifluoromethyl)benzoate

1415089-89-2
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Yield:1415089-89-2 66.5%

Reaction Conditions:

with zinc;1,1'-bis-(diphenylphosphino)ferrocene;tris-(dibenzylideneacetone)dipalladium(0) in ISOPROPYLAMIDE at 85; for 12 h;

Steps:

24 Methyl 5-cyano-2-(trifluoromethyl)benzoate

Dissolve methyl 5-chloro-2-(trifluoromethyl)benzoate (500 mg, 2.1 mmol), zinc (II) cyanide (197 mg, 1.68 mmol), zinc (55 mg, 0.84 mmol), di-palladium (II) tris(dibenzylideneacetone) (192 mg, 0.21 mmol), and diphenylphosphino ferrocene (233 mg, 0.42 mmol) in dimethylacetamide (20 mL). Heat the reaction mixture to 85° C., and stir for 12 hours. Pour the resulting mixture into water, and extract with EtOAc (2*100 mL). Dry the combined organics over sodium sulfate; filter; collect the filtrate; and concentrate the filtrate under reduced pressure. Purify the residue by silica gel chromatography eluting with 50:1 petroleum ether:EtOAc to give the title compound (320 mg, 66.5% yield) as a white solid. 1H NMR (300 MHz, CDCl3,) δ 8.09 (s, 1H), 7.90 (s, 2H), 3.80 (s, 3H).

References:

US2012/302608,2012,A1 Location in patent:Page/Page column 8

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