[Br:1][C:2]1[CH:7]=[CH:6][C:5](I)=[C:4]([CH3:9])[CH:3]=1.[Br-].[S:11]1[CH:15]=[CH:14][CH:13]=[C:12]1[Zn+]>C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.C1COCC1>[Br:1][C:2]1[CH:7]=[CH:6][C:5]([C:12]2[S:11][CH:15]=[CH:14][CH:13]=2)=[C:4]([CH3:9])[CH:3]=14-Bromo-2-methyliodobenzene (1.0 mmol) was combined with THF solution of 2-thienylzinc bromide (2.0 mmol) in an oven-dried tube under argon. The resulting solution was degassed with a steady stream of argon for 10 min at rt. To this mixture, solid (Ph3P)4Pd (0.1 mmol) was added and the mixture was degassed with argon for 2 min after which it was stirred at rt for 8 h. The reaction mixture was combined with 1M HCl (100 mL) and ethyl acetate (200 mL). Organic layer was separated, washed sequentially with 1M hydrochloric acid (50 mL) and brine (50 mL), and dried over sodium sulfate. The desired product was isolated by flash chromatography on silica gel using hexanes as the eluant: 1H NMR (CDCl3) 7.45 (d, J=1.0, 1H), 7.39 (d, J=5.6, 1H), 7.37 (dd, J=1.0, 5.0, 1H), 7.28 (d, J=5.0, 1H), 7.13 (m, 1H), 7.08 (d, J=5.6, 1H); HPLC A 4.09 min; ESI-MS (m/z)=252, 254.
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