N-bromobutanimide → 3-Bromo-4-(bromomethyl)benzonitrile

Participants

Reaction Conditions

Reaction Steps

A solution of 3-bromo-4-methylbenzonitrile (1 g, 5.10 mmol) in chloroform (20 mL) was heated to 40-50° C. and N-bromosuccinimide (0.953 g, 5.36 mmol) was added in one portion followed by AIBN (8.38 mg, 0.051 mmol). After 1.5 hr. additional AIBN (20 mg) was added and the reaction was allowed to stir at 50° C. overnight. Additional AIBN (20 mg) and N-bromosuccinimide (1.1 g) were added, a reflux condenser was attached and the solution was heated to reflux. After several hours, additional AIBN (20 mg) was added and the reaction was allowed to stir at reflux overnight. The reaction was quenched by the addition of water and sat. aq. sodium bicarbonate. The organic phase was separated, concentrated in vacuo and purified by flash column chromatography (120 g silica, eluting with 0%-20% Ethyl Acetate in hexanes) to afford 3-bromo-4-(bromomethyl)benzonitrile as a pale yellow solid (800 mg, 2.88 mmol). 1H NMR (500 MHz, MeOD) δ ppm 4.70 (s, 2H), 7.71 (d, J=8.0 Hz, 1H), 7.73 (d, J=8.0 Hz, 1H), 8.04 (s, 1H).

Provenance & Evidence