[CH3:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][C:9]=2[C:14]2[S:15][CH:16]=[CH:17][CH:18]=2)=[CH:4][CH:3]=1.CC(N=NC(C#N)(C)C)(C#N)C.[Br:31]N1C(=O)CCC1=O>C(Cl)(Cl)(Cl)Cl>[Br:31][CH2:1][C:2]1[CH:3]=[CH:4][C:5]([C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][C:9]=2[C:14]2[S:15][CH:16]=[CH:17][CH:18]=2)=[CH:6][CH:7]=1A solution of 123 mg (0.492 mmol) of 4-methyl-2'-(2-thienyl)-1,1'-biphenyl, 18.5 mg of AIBN and 110 mg (0.62 mmol) of N-bromosuccinimide in 50 mL of carbon tetrachloride was heated at reflux until a negative starch iodide reaction was obtained (2 hr). The reaction mixture was evaporated under vacuum and the residue triturated with hexane. The hexane washes were filtered and the filtrate evaporated under vacuum to give 158 mg of product. 1H NMR (300 MHz, CDCl3): 4.48 (s, 2H), 6.68 (dd, 1H), 6.88 (dd, 1H), 7.11 (m, 5H), 7.36 (m, 3H), 7.50 (dd, 1H).
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