Benzoyl Peroxide → 2-(Bromomethyl)benzo[d]oxazole

Participants

Reaction Steps

509.8 mg of dibenzoyl peroxide were added to a solution of 56 ml of 2-methylbenzoxazole and 18.73 g of N-bromosuccinimide in 20 ml of carbon tetrachloride at room temperature and the resulting mixture was stirred under reflux for 6 hours. At the end of this time, the reaction mixture was filtered and the resulting filtrate was concentrated by evaporation under reduced pressure to give a crude crystalline solid. This was dissolved in ethyl acetate and then washed consecutively with a saturated aqueous sodium sulfite solution, water and a saturated aqueous sodium chloride solution and then dried over anhydrous sodium sulfate. The solvent was then removed by evaporation under reduced pressure to give a crude residue which was purified by column chromatography through silica gel using a 10:1 by volume mixture of hexane and ethyl acetate to give 3.34 g (yield 37%) of the title compound as an oil.

Provenance & Evidence