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

Participants

Reaction Conditions

Reaction Steps

In a 3-neck 100 mL round-bottomed flask, 3-bromo-5-(trifluoromethyl)benzoic acid (10.0, 1.0 eq.) was dissolved in DMF (100 mL, 10 Vol). CuCN was added at RT and the reaction was stirred at 150° C. for 15-16 hr. Reaction completion was monitored on TLC using MeOH:dichloromethane (1:9) mobile phase. Reaction mixture was quenched into the ice-water slurry (1000 mL) and filtered over celite. Compound was extracted in the ethyl acetate (250 mL×3). Organic layer was washed with water (150 mL) followed by drying using anhydrous sodium sulphate. Organic layer was concentrated under reduced pressure. Then again the crude was dissolved in ethyl acetate and extracted with (250 mL×3). Combined aqueous layer was again acidified with dil HCl (350 mL) to get pH 3. Then aqueous layer was extracted with ethyl acetate (250 mL×3). This combined organic layer was washed with water (150 mL) followed by drying using anhydrous sodium sulphate. Organic layer was concentrated under reduced pressure to afford 6.0 g of crude compound, Yield (75.4%). This crude material was directly used for next step without purification; Mass: (ES−) 214.14 (M−1).

Provenance & Evidence