Reaktion #9053

Reaktionsgleichung

5-methylbenzoxazole

N-bromosuccinimide

2,2′-azobisisobutyronitrile

→

title compound

Ausbeute 39.6%

5-bromomethyl-benzoxazole

Ausbeute 39.6%

Lösungsmittel

CCl4

Reaktionsbedingungen

Aufarbeitung

1. 1
   Temperaturwas heated
2. 2
   Temperaturat reflux for 22 h
3. 3
   FiltrationThe mixture was filtered
4. 4
   Einengenthe filtrate was concentrated under reduced pressure
5. 5
   SonstigePurification of the crude material on silica gel (5% EtOAc/hexanes)

Vorschrift

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).

Quelle