N-bromobutanimide → Methyl 4-bromomethyl-3-cyanobenzoate

Participants

Reaction Steps

A mixture of methyl 3-cyano-4-methylbenzoate (1.78 g, 9.79 mmol) and NBS (1.92 g, 10.8 mmol) in CCl4 (150 mL) was irradiated with a 150W tungsten lamp at 50 C. for 2 h. The reaction was cooled, filtered, and concentrated. The residue was chromatographed (250 g silica, 10% EtOAc/hexanes to 15% EtOAc/hexanes) to give the title compound (1.20 g, 48%); IR(CHCl3: 1291, 1302, 1439, 1728 cm−1; NMR(300 MHz, CDCl3): 4.01 (s, 3H); 4.67 (s, 3H); 7.66 (d, 1H, J=8.1 Hz); 8.24 (d, 1H, J=8.7 Hz); 8.34 (s, 1H); MS(FD): 253.0.

Provenance & Evidence