[Cl:1][C:2]1[CH:3]=[C:4]([SH:9])[CH:5]=[CH:6][C:7]=1[F:8].[OH-].[K+].I[C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][C:14]=1[CH2:19][C:20]([OH:22])=[O:21]>O.[Cu]>[Cl:1][C:2]1[CH:3]=[C:4]([S:9][C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][C:14]=2[CH2:19][C:20]([OH:22])=[O:21])[CH:5]=[CH:6][C:7]=1[F:8]The thiophenol from the preceding experiment (34.5 g) is added at 50° C. to a solution of potassium hydroxide (40 g) in water (425 ml) and this mixture is stirred until it becomes homogeneous. Then, o-iodophenylacetic acid (55.0 g) and copper powder (2.0 g) are added and the mixture refluxed for 24 hours. While still warm, the solution is filtered with charcoal, the filtrate diluted with water and acidified with hydrochloric acid. The separated crude oily acid is extracted with benzene, the solvent evaporated and the residue crystallized from aqueous ethanol, yielding 45.2 g (72%) of 2-(3-chloro-4-fluorophenylthio)phenylacetic acid which in the pure state melts at 85°-87° C. (cyclohexane-hexane).
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