Dimethylformamide → Methyl 4-cyano-2-fluorobenzoate

Participants

Reaction Conditions

Reaction Steps

A solution of methyl 4-bromo-2-fluorobenzoate (10.0 g, 43 mmol), zinc cyamide (10.0 g, 86 mmol) and palladium tetrakis(triphenylphosphine) (2.5 g, 0.64 mmol) in anhydrous N,N-dimethylformamide (100 mL) was purged with nitrogen and the mixture stirred at 80° C. overnight. After cooling, the mixture was partitioned between ethyl acetate and brine and the organic phase washed with water and concentrated. The solid was purified on silica gel using 1:5 ethyl acetate/hexane to afford the title compound (6.1 g, 80%). MS (DCI): m/z 180 (M+H)+.

Provenance & Evidence