3-Bromo-5-(trifluoromethyl)benzoic acid → 3-Cyano-5-(trifluoromethyl)benzoic acid

Participants

Reaction Conditions

Reaction Steps

A mixture of 2.0 g (7.43 mmol) of 3-bromo-5-(trifluoromethyl)benzoic acid [US 2006/0069261-A1, compound 1.2], 995 mg (8.48 mmol) of zinc cyanide and 859 mg (0.743 mmol) of tetrakis-(triphenylphosphine)palladium(0) in 75 ml of DMF/water (99:1) was initially degassed and then, under an atmosphere of argon, heated at 120° C. for 3 h. After cooling to RT, the mixture was diluted with about 300 ml of water and extracted three times with in each case about 150 ml of ethyl acetate. The combined organic extracts were washed with saturated sodium chloride solution, dried over anhydrous magnesium sulphate, filtered and then concentrated to dryness on a rotary evaporator. The product was isolated by preparative HPLC (Method 9). Evaporation of the product fractions and drying of the residue under high vacuum gave 421 mg (26% of theory) of the title compound.

Provenance & Evidence