[C:1]([C:3]1[S:4][C:5]([CH3:8])=[CH:6][CH:7]=1)#[N:2].[Br:9]N1C(=O)CCC1=O.N(C(C)(C)C#N)=NC(C)(C)C#N>C(Cl)(Cl)(Cl)Cl>[C:1]([C:3]1[S:4][C:5]([CH2:8][Br:9])=[CH:6][CH:7]=1)#[N:2]A solution of 2-cyano-5-methylthiophene (compound 3-2, 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); 1H NMR (CDCl3): δ 4.66 (s, 2H), 7.10 (d, 1H, J=3.8 Hz), 7.48 (d, 1H, J=3.8 Hz).
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