Reacción #9053

Ecuación de reacción

5-methylbenzoxazole

N-bromosuccinimide

2,2′-azobisisobutyronitrile

→

title compound

Rendimiento 39.6%

5-bromomethyl-benzoxazole

Rendimiento 39.6%

Disolventes

CCl4

Condiciones de reacción

Tratamiento posterior

1. 1
   Temperaturawas heated
2. 2
   Temperaturaat reflux for 22 h
3. 3
   FiltraciónThe mixture was filtered
4. 4
   Concentraciónthe filtrate was concentrated under reduced pressure
5. 5
   OtroPurification of the crude material on silica gel (5% EtOAc/hexanes)

Procedimiento

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).

Fuente