N-bromobutanimide → 3-(Bromomethyl)-5-methylbenzonitrile

Participants

Reaction Steps

To a stirred solution of carbon tetrachloride (270 mL), was added 3,5-dimethylbenzonitrile (37 g, 0.282 M), N-bromo succinimide (NBS) (50 g, 0.282 M), and benzoyl peroxide (3.4 g, 14 mmol). The mixture was then refluxed for 3 hr. under a 500 W tungsten lamp. After cooling to room temperature, the mixture was filtered, evaporated, and the residue was purified by silica gel column chromatography (eluent, ether:hexane (1:10)) to give 48 g (81%) of 3-(bromomethyl)-5-methylbenzonitrile as a white solid. m.p. 80-81° C. 1H NMR (200 MHz, CDCl3) δ 2.39 (3H, s), 4.43 (2H, s), 7.39 (1H, s), 7.43 (1H, s), 7.48 (1H, s).

Provenance & Evidence