Reaction #7820

Reaction equation

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

benzoyl peroxide

N-bromosuccinimide

→

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

Solvents

carbon tetrachloride

Conditions

Workup

1. 1
   Temperatureto reflux conditions under argon
2. 2
   Filtrationfiltered
3. 3
   Washwashing with dichoromethane
4. 4
   ConcentrationAfter concentrating filtrate in vacuo
5. 5
   Otherthe resulting colorless solid was purified by flash chromatography
6. 6
   Washa gradient elution of 1:4 EtOAc

Procedure

2-(3-Methoxy-4-methylphenyl)-1,3-benzoxazole (1.0 g, 4.1 mmol), carbon tetrachloride (18 mL), benzoyl peroxide (66 mg, 0.3 mmol) and N-bromosuccinimide (970 mg, 5.4 mmol) was heated to reflux conditions under argon and placed under a UV light. After one hour, no starting material was observed by TLC. After cooling mixture to rt, filtered, washing with dichoromethane. After concentrating filtrate in vacuo, the resulting colorless solid was purified by flash chromatography, using a gradient elution of 1:4 EtOAc:hexanes to EtOAc. This afforded the desired intermediate, 2-[4-(bromomethyl)-3-methoxyphenyl]-1,3-benzoxazole, as a colorless solid.

Source