反応 #7820

反応方程式

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

benzoyl peroxide

N-bromosuccinimide

→

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

溶媒

carbon tetrachloride

反応条件

後処理

1. 1
   温度to reflux conditions under argon
2. 2
   ろ過filtered
3. 3
   洗浄washing with dichoromethane
4. 4
   濃縮After concentrating filtrate in vacuo
5. 5
   その他the resulting colorless solid was purified by flash chromatography
6. 6
   洗浄a gradient elution of 1:4 EtOAc

実験手順

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.

出典