Azobisisobutyronitrile → 5-(Bromomethyl)thiophene-2-carbonitrile

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Reaction Steps

A solution of 2-cyano-5-methylthiophene (compound 23, 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 its reflux temperature 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 of hexane/ethyl acetate) to give the title compound (4.5 g, 91%). TLC: Rf 0.91 (1:1 of hexane/ethyl acetate); 1H NMR (CDCl3): δ 4.66 (s, 2H), 7.10 (d, 1H, J=3.8 Hz), 7.48 (d, 1H, J=3.8 Hz).

Provenance & Evidence