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

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.

1. temperatureunder reflux for 6 hours
2. filtrationAt the end of this time, the reaction mixture was filtered
3. concentrationthe resulting filtrate was concentrated by evaporation under reduced pressure
4. customto give a crude crystalline solid
5. washwashed consecutively with a saturated aqueous sodium sulfite solution, water
6. dry with materiala saturated aqueous sodium chloride solution and then dried over anhydrous sodium sulfate
7. customThe solvent was then removed by evaporation under reduced pressure
8. customto give a crude residue which
9. customwas purified by column chromatography through silica gel using a 10:1
10. additionby volume mixture of hexane and ethyl acetate

ORD record

ord-ac78ab670d8845f599ebf8aa8fd8f73d

Source dataset

uspto-grants-1998_04

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US05736487