[Cl:1][C:2]1[CH:3]=[C:4]([C:8]2[S:9][CH:10]=[CH:11][CH:12]=2)[CH:5]=[CH:6][CH:7]=1.[C:13]1([S:19]Cl)[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1>[Fe].C(Cl)(Cl)(Cl)Cl>[Cl:1][C:2]1[CH:3]=[C:4]([C:8]2[S:9][C:10]([S:19][C:13]3[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=3)=[CH:11][CH:12]=2)[CH:5]=[CH:6][CH:7]=1A mixture of 89 g (0.46 mole) of 2-(m-chlorophenyl)thiophene, 400 ml of reagent carbon tetrachloride, 54 ml (67 g, 0.46 mole) of benzenesulfenyl chloride and 0.05 g of iron powder was allowed to stand for four days at room temperature. A further 12 ml (15 g, 0.10 mole) of benzenesulfenyl chloride and 0.05 g of iron powder were added. After four days the carbon tetrachloride was removed by distillation. The residue was distilled at reduced pressure to give 30 g (22%) of 2-(m-chlorophenyl)-5-(phenylthio)thiophene, b.p. 200°-205° C. (0.15 mm).
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