CN(C)C(=O)C.C1([SH:13])C=CC=CC=1.Br[C:15]1[CH:23]=[CH:22][C:18]([C:19]([OH:21])=O)=[CH:17][CH:16]=1.[CH:24]1[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1>[OH-].[K+]>[C:24]1([C:15]2[CH:16]=[CH:17][C:18]([C:19]([OH:21])=[S:13])=[CH:22][CH:23]=2)[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1A solution of 70 ml of N,N-dimethylacetamide in which 20.86 g of potassium hydroxide was dissolved was heated to 150° C., and 19.52 ml of thiophenol and 25.47 g of 4-bromobenzoic acid were added under nitrogen atmosphere while stirring at the same temperature. After reflux for 20 hours under nitrogen atmosphere, the reaction mixture was poured into 400 ml of ice water, and 400 ml of benzene was added to wash, and the water layer was separated. The benzene layer was extracted with 2.5N sodium hydroxide (100 ml×4). The extract was combined with the water layer and the pH was adjusted to 1 to 2 with concentrated hydrochloric acid, and the precipitate was filtered, washed in water, dried, and 4-phenylthiobenzoic acid was obtained (26.29 g).
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