N-bromobutanimide → 1-Bromo-3-(bromomethyl)-5-methylbenzene

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The mixture of 3,5-dimethylbromobenzene (80.25 g, 0.43M), NBS (77 g, 0.43M), and benzoyl peroxide (5.2 g, 0.021M) in carbon tetrachloride (400 ml) was refluxed for 3 hr. under a light of 500 W tungsten light. After cooling to room temperature, the mixture was filtered and the filtrate was evaporated in vacuo to give a white solid, which was purified by silica gel column chromatography (eluent, hexane) to afford 82 g (72%) of a white solid; m.p. 46-47° C.; 1H NMR (200 MHz, CDCl3) δδ 2.32 (3H, s), 4.38 (2H, s), 7.12 (1H, s), 7.25 (1H, s), 7.33 (1H, s).

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