Реакция #9053

Уравнение реакции

5-methylbenzoxazole

N-bromosuccinimide

2,2′-azobisisobutyronitrile

→

title compound

Выход 39.6%

5-bromomethyl-benzoxazole

Выход 39.6%

Растворители

CCl4

Условия реакции

Обработка

1. 1
   Температураwas heated
2. 2
   Температураat reflux for 22 h
3. 3
   ФильтрацияThe mixture was filtered
4. 4
   Концентрированиеthe filtrate was concentrated under reduced pressure
5. 5
   ДругоеPurification of the crude material on silica gel (5% EtOAc/hexanes)

Методика

A mixture of 5-methylbenzoxazole (200 mg, 1.50 mmol), N-bromosuccinimide (321 mg, 1.80 mmol), and 2,2′-azobisisobutyronitrile (37 mg, 0.23 mmol) in CCl4 (3 mL) was heated at reflux for 22 h. The mixture was filtered and the filtrate was concentrated under reduced pressure. Purification of the crude material on silica gel (5% EtOAc/hexanes) gave the title compound as a colourless crystals (126 mg, 39%). 1H NMR (CDCl3) δ 4.64 (s, 2H), 7.46 (dd, 1H, J=8.6, 1.7 Hz), 7.57 (d, 1H, J=8.4 Hz), 7.83 (d, 1H, J=1.2 Hz), 8.12 (s, 1H).

Источник