Reacción #1350604

Ecuación de reacción

2-cyano-5-methylthiophene

compound 22

2-cyano-5-methylthiophene

N-bromosuccinimide

2,2′-azobisisobutyronitrile

→

title compound

Rendimiento 92.8%

2-cyano-5-(bromomethyl)thiophene

Rendimiento 92.8%

Disolventes

CCl4

Condiciones de reacción

Tratamiento posterior

1. 1
   Temperaturaat reflux for 5 hours
2. 2
   Otrothe solvent was removed under vacuum
3. 3
   Otroto give a yellow oil
4. 4
   OtroThe oil was purified by a flash column chromatography (1:1 hexane/ethyl acetate)

Procedimiento

A solution of 2-cyano-5-methylthiophene (compound 22, 3.0 g, 24 mmol), N-bromosuccinimide (Aldrich, 4.8 g, 27 mmol), and 2,2′-azobisisobutyronitrile (Aldrich, 0.4 g, 2.4 mmol) in CCl4 (Aldrich, 60 mL) was heated at reflux for 5 hours. After cooling to ambient temperature, the solvent was removed under vacuum to give a yellow oil. The oil was purified by a flash column chromatography (1:1 hexane/ethyl acetate) to give the title compound (4.5 g, 91%). TLC Rf 0.91 (1:1 of hexane/ethyl acetate); 1HNMR (CDCl3) δ4.66 (s, 2H), 7.10 (d, 1H, J=3.8 Hz), 7.48 (d, 1H, J=3.8 Hz).

Fuente