Dimethylformamide → Methyl 4-cyano-2-methylbenzoate

Participants

Reaction Steps

To a solution of methyl 4-bromo-2-methylbenzoate (26.6 g, 0.116 mol) in DMF (300 mL) was added zinc cyanide (8.1 g, 0.07 mol) followed by tetrakis(triphenylphosphine)palladium(0) (6.7 g, 0.0058 mol). The reaction mixture was placed in a 100° C. oil bath and stirred for 2 h, at which time it was filtered through a bed of celite and the filter cake rinsed with ethyl acetate. The filtrate was concentrated in vacuo and the residue was purified by flash chromatography (10% ethyl acetate in hexanes) to afford methyl 4-cyano-2-methylbenzoate (18.1 g, 89%) as a white powder. 1H NMR (400 MHz, CDCl3): 7.97 (d, 1H), 7.55 (s, 1H), 7.53 (br m, 1H), 3.93 (s, 3H), 2.62 (s, 3H).

Provenance & Evidence