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

Participants

Reaction Steps

A mixture of 1-bromo-3,5-dimethylbenzene (25.0 g, 135 mmol), NBS (24.0 g, 135 mmol) and BPO (1.30 g) in CCl4 (250 mL) was refluxed for 6 h. After cooling to room temperature, the mixture was filtered, and the filtrate was washed successively with saturated sodium bicarbonate (100 mL), water (2×50 mL) and brine (2×50 mL). The combined organic phases were dried (Na2SO4) and concentrated in vacuum to give 40.0 g of crude product 1-bromo-3-(bromomethyl)-5-methylbenzene.

Provenance & Evidence