Dimethylformamide → Methyl 4-cyano-2-methylbenzoate

Participants

Reaction Conditions

Reaction Steps

A mixture of methyl 4-bromo-2-methylbenzoate (1 g, 4.4 mmol), zinc cyanide (0.7 g, 6.0 mmol) and tetrakis(triphenylphosphine)palladium(0) (100 mg, 0.086 mmol) in N,N-dimethylformamide was heated to 140° C. under nitrogen atmosphere. And then the mixture stirred under reflux condition for 12 hours. The mixture was cooled to room temperature, and partitioned between dichloromethane (20 mL*3) and brine (60 mL). The organic layer was concentrated to dryness and the residue was purified by column chromatography (silica gel, petroleum ether/ethyl acetate=15:1) to give methyl 4-cyano-2-methylbenzoate as a white solid (200 mg, 26%). LRMS (M+H+) m/z: calcd 175.06. found 175. 1H NMR (300 MHz, CDCl3): δ 7.97 (d, J=8.7 Hz, 1H), 7.57-7.53 (m, 2H), 3.93 (s, 3H), 2.62 (s, 3H).

Provenance & Evidence