Reacción #1684997

Ecuación de reacción

dibenzoyl peroxide

2-methylbenzoxazole

N-bromosuccinimide

→

title compound

Rendimiento 37.0%

2-Bromomethylbenzoxazole

Rendimiento 37.0%

Disolventes

carbon tetrachloride

ethyl acetate

Condiciones de reacción

Tratamiento posterior

1. 1
   Temperaturaunder reflux for 6 hours
2. 2
   FiltraciónAt the end of this time, the reaction mixture was filtered
3. 3
   Concentraciónthe resulting filtrate was concentrated by evaporation under reduced pressure
4. 4
   Otroto give a crude crystalline solid
5. 5
   Lavadowashed consecutively with a saturated aqueous sodium sulfite solution, water
6. 6
   Secadoa saturated aqueous sodium chloride solution and then dried over anhydrous sodium sulfate
7. 7
   OtroThe solvent was then removed by evaporation under reduced pressure
8. 8
   Otroto give a crude residue which
9. 9
   Otrowas purified by column chromatography through silica gel using a 10:1
10. 10
    workup.ADDITIONby volume mixture of hexane and ethyl acetate

Procedimiento

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.

Fuente