Reaktion #7820

Reaktionsgleichung

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

benzoyl peroxide

N-bromosuccinimide

→

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

Lösungsmittel

carbon tetrachloride

Reaktionsbedingungen

Aufarbeitung

1. 1
   Temperaturto reflux conditions under argon
2. 2
   Filtrationfiltered
3. 3
   Waschenwashing with dichoromethane
4. 4
   EinengenAfter concentrating filtrate in vacuo
5. 5
   Sonstigethe resulting colorless solid was purified by flash chromatography
6. 6
   Waschena gradient elution of 1:4 EtOAc

Vorschrift

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.

Quelle