Br[C:2]1[C:3]2[CH:10]=[CH:9][CH:8]=[CH:7][C:4]=2[S:5][CH:6]=1.C1(C)C=CC=CC=1.[CH3:18][O:19][C:20]1[CH:25]=[CH:24][C:23](B(O)O)=[CH:22][CH:21]=1>CO.CCOCC.CCCCCCC.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>[CH3:18][O:19][C:20]1[CH:25]=[CH:24][C:23]([C:2]2[C:3]3[CH:10]=[CH:9][CH:8]=[CH:7][C:4]=3[S:5][CH:6]=2)=[CH:22][CH:21]=1Mix 3-bromobenzo[b]thiophene (5.83 g, 27.4 mmol), tetrakis(triphenylphosphine)palladium (O) (1.00 g, 0.865 mmol) and toluene (60 mL) and purge with nitrogen. Rapidly, add a 2 M aqueous solution of sodium carbonate (27 mL) and purge with nitrogen. Add a solution of 4-methoxyphenylboronic acid (4.57 g, 30.1 mmol) in methanol (13 mL), purge with nitrogen and heat at a gentle reflux for 4.5 hours. Let cool and stir at room temperature, overnight. TLC (30% dicloromethane in heptane) shows that all starting material is consumed. Dilute reaction mixture with ethyl acetate (100 mL). Wash with 2 M sodium carbonate (75 mL), water (75 mL), saturated sodium chloride (75 mL), dry (MgSO4) and concentrate (in vacuo) to give a residue. Purify the residue by column (silica) chromatography (20% dichloromethane in heptane) to give a mixture as a residue. Dissolve the residue in 30% ether in heptane, filter, evaporate and dry (0.5 mm Hg, room temperature) to give the title compound as a clear oil (5.47 g, 83% Yield).
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