[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([C:9]2[C:14]3[CH:15]=[CH:16][S:17][C:13]=3[CH:12]=[CH:11][CH:10]=2)=[CH:5][CH:4]=1.C(Cl)Cl.C(=O)=O.[Br:24]Br>CC(C)=O.O>[Br:24][C:12]1[C:13]2[S:17][CH:16]=[CH:15][C:14]=2[C:9]([C:6]2[CH:7]=[CH:8][C:3]([O:2][CH3:1])=[CH:4][CH:5]=2)=[CH:10][CH:11]=1To a 25 ml round bottom flask was added 4-(4-methoxyphenyl)-1-benzothiophene (500 mg, 2.08 mmol), CH2Cl2 (10 ml), and the solution was cooled to −20° C. (acetone-water, CO2). Bromine (8.33 ml of 0.25 M stock in CH2Cl2, 2.08 mmol) was slowly added dropwise over 0.5 h and the reaction was stirred for a additional 0.5 h. The reaction was then washed with water, dried over anhydrous Na2SO4, passed through a silica plug and concentrated to 460 mg orange oil. Recrystallization from 3:97 EtOAc-hexanes afforded 350 mg (53%) of product as white crystals: 1H NMR (300 MHz, DMSO-d6): δ 3.83 (3H, s), 7.10 (2H, d, J=8.0 Hz), 7.31 (1H, d, J=7.9 Hz), 7.51 (2H, d, J=8.4 Hz), 7.56 (1H, d, J=5.6 Hz), 7.68 (1H, d, J=7.9 Hz), 7.92 (1H, d, J=5.6 Hz).
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