Reaction #7779

Reaction equation

2-(3-bromo-4-methylphenyl)-1,3-benzoxazole

n-bromosuccinimide

benzoyl peroxide

→

2-[3-bromo-4-(bromomethyl)phenyl]-1,3-benzoxazole

Solvents

carbon tetrachloride

Conditions

Workup

1. 1
   Temperaturewas refluxed for 3 h
2. 2
   FiltrationThe white precipitate was filtered
3. 3
   Otherthe filtrate was evaporated to dryness
4. 4
   OtherThe resulting solid was purified by flash chromatography on silica gel eluting with EtOAc:hexane (1:5)

Procedure

A mixture of 2-(3-bromo-4-methylphenyl)-1,3-benzoxazole (240 mg, 0.83 mmol), n-bromosuccinimide (180 mg, 0.99 mmol), and benzoyl peroxide (10 mg, 0.041 mmol) in carbon tetrachloride (15 mL) was refluxed for 3 h. The white precipitate was filtered and the filtrate was evaporated to dryness. The resulting solid was purified by flash chromatography on silica gel eluting with EtOAc:hexane (1:5) to afford 2-[3-bromo-4-(bromomethyl)phenyl]-1,3-benzoxazole as a yellow solid.

Source