1,3-Dibromo-5,5-dimethylhydantoin → 1-Bromo-3-(bromomethyl)-5-methylbenzene

Participants

Reaction Steps

To a solution of 1-bromo-3,5-dimethylbenzene (25.0 g, 135.0 mmol) in CCl4 (150 mL), 1,3-dibromo-5,5-dimethylimidazolidine-2,4-dione (14.5 g, 54.0 mmol) and dibenzoyl peroxide (BPO) (0.2 g) were added and the mixture was refluxed for 7 h. After the reaction was cooled to room temperature, the precipitate was filtered though Celite, and then the solid was rinsed two times with pentane (50 mL). The combined filtrate was washed with water (50 mL), followed by saturated sodium bicarbonate (50 mL) and sodium thiosulfate (50 mL×2). The organic layer was dried over anhydrous sodium sulfate. Evaporation of the solvent afforded the compound 1-bromo-3-(bromomethyl)-5-methylbenzene (35.6 g, 99%).

Provenance & Evidence