Benzoyl Peroxide → 7-(Bromomethyl)-1-benzothiophene

Participants

Reaction Steps

To a solution of 7-methylbenzo[b]thiophene (1.0 g, 6.5 mmol) in CCl4 (20 mL) was added benzoyl peroxide (1.1 g, 4.54 mmol) followed by portionwise addition of NBS (1.15 g, 6.5 mmol). The reaction mixture stirred at reflux while irradiating with a 250 W lamp. The reaction mixture was stirred at reflux for 3 h. The solution was cooled, filtered and the solvent evaporated in vacuo. The residue was subjected to column chromatography on silica gel with hexanes as the eluent to afford the title compound (0.570 g, 33% yield): 1H NMR (400 MHz, CDCl3) δ: 7.80 (1H, dd, J=7.8, 1.7 Hz), 7.49 (1H, d, J=5.4 Hz), 7.40-7.33 (3H, m), 4.78 (2H, s). LCMS (M+H)+ m/z 209.

Provenance & Evidence