[CH3:1][S:2][C:3]1[CH:8]=[CH:7][C:6]([C:9]2[CH:13]=[CH:12][S:11][C:10]=2[C:14]2[CH:19]=[CH:18][C:17]([N+:20]([O-:22])=[O:21])=[CH:16][CH:15]=2)=[CH:5][CH:4]=1.[Cl:23]N1C(=O)CCC1=O.C(=O)(O)[O-].[Na+]>C(O)(=O)C>[Cl:23][C:12]1[S:11][C:10]([C:14]2[CH:19]=[CH:18][C:17]([N+:20]([O-:22])=[O:21])=[CH:16][CH:15]=2)=[C:9]([C:6]2[CH:5]=[CH:4][C:3]([S:2][CH3:1])=[CH:8][CH:7]=2)[CH:13]=1A mixture of 3-[4-(methylthio)phenyl]-2-(4-nitrophenyl)thiophene (0.33 g) and N-chlorosuccinimide (0.15 g) in acetic acid (5 ml) was heated at 80° C. for 3 hours. The mixture was poured into an ice-cooled solution of sodium bicarbonate, and the precipitates were collected to give a powder of 5-chloro-3-[4-(methylthio)phenyl]-2(4-nitrophenyl)thiophene (0.31 g).
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