Benzoyl Peroxide → 1,3-Dibromo-2-(bromomethyl)benzene

Participants

Reaction Conditions

Reaction Steps

A mixture of 2,6-dibromotoluene (22.9 g, 92 mmol), N-bromosuccinimide (NBS) (15 g, 84 mmol), CCl4 (250 mL) and benzoyl peroxide (0.03 eq) was stirred at 85° C. (hot oil bath temperature) for 16 h, cooled to RT, filtered, washed with aq. NaHSO3, dried (Na2SO4), filtered, and evaporated to give 29.5 g (yield of 98%) of title product as a white solid. This solid contained 10% unreacted starting material but was successfully used without further purification. 1H NMR (300 MHz, CDCl3) δ 4.81 (s, 2H), 7.01 (t, 1H), 7.53 (d, 2H).

Provenance & Evidence