Benzoyl Peroxide → 5-Bromo-7-bromomethylbenzofuran

Participants

Reaction Steps

N-Bromosuccinimide (10.0 g) and di-benzoylperoxide (500 mg) were added in five equal portions to a solution of 5-bromo-7-methylbenzofuran (9.7 g) stirring at reflux in CCl4 (100 ml), whilst being irradiated with an 850 W lamp. After the final addition, the reaction was stirred at reflux for a further 2 hours, then cooled to room temperature. The solution was filtered and the filtrate washed with 2N NaOH--H2O (40 ml), brine (40 ml), dried over MgSO4, filtered and the solvent removed under reduced pressure. Purification by MPLC (1% ethyl acetateln-hexane) gave 5-bromo-7-bromomethyl benzofuran as a dlear oil (4.2 g). 1H NMR (360 MHz,CDCl3)δ4.86 (2H, s), 6.69 (1H, d, J=3.0 Hz), 7.54 (1H, s), 7.62 (1H, s), 7.86 (1H, d, J=3.0 Hz).

Provenance & Evidence