Reaction #7789

Reaction equation

2-[4-methyl-3-(trifluoromethyl)phenyl]-1,3-benzoxazole

n-bromosuccinimide

benzoyl peroxide

→

2-[4-(bromomethyl)-3-(trifluoromethyl)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
   Concentrationthe filtrate was concentrated to dryness
4. 4
   OtherThe crude was purified by flash chromatography on silica gel eluting with EtOAc:hexanes (1:1)

Procedure

A mixture of 2-[4-methyl-3-(trifluoromethyl)phenyl]-1,3-benzoxazole (600 mg, 2.2 mmol), n-bromosuccinimide (579 mg, 3.25 mmol), benzoyl peroxide (26 mg, 0.11 mmol) in carbon tetrachloride (15 mL) was refluxed for 3 h and then cooled to rt. The white precipitate was filtered and the filtrate was concentrated to dryness. The crude was purified by flash chromatography on silica gel eluting with EtOAc:hexanes (1:1) to afford 2-[4-(bromomethyl)-3-(trifluoromethyl)phenyl]-1,3-benzoxazole.

Source