[Br:1][C:2]1[CH:3]=[CH:4][C:5]2[S:9][CH:8]=[C:7]([CH3:10])[C:6]=2[CH:11]=1.[Br:12]N1C(=O)CCC1=O>C(Cl)(Cl)(Cl)Cl.C(OOC(=O)C1C=CC=CC=1)(=O)C1C=CC=CC=1>[Br:1][C:2]1[CH:3]=[CH:4][C:5]2[S:9][CH:8]=[C:7]([CH2:10][Br:12])[C:6]=2[CH:11]=1A solution of 4.30 gm (18.9 mMol) 5-bromo-3-methylbenzothiophene, 0.25 gm (1.03 mMol) benzoylperoxide, and 3.37 gm (18.9 mMol) N-bromosuccinimide in 50 mL carbon tetrachloride was heated at reflux for 3 hours. The reaction mixture was cooled to room temperature, filtered and the filtrate concentrated under reduced pressure. The residue was subjected to flash silica gel chromatography, eluting with hexane. Fractions containing the desired compound were combined and concentrated under reduced pressure to provide 4.28 gm (74%) of the desired compound.
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