C(=O)([O-])[O-].[K+].[K+].[OH:7][C:8]1[CH:13]=[CH:12][C:11]([SH:14])=[CH:10][CH:9]=1.C1(C)C=CC(S(O[CH2:25][C:26]([F:29])([F:28])[F:27])(=O)=O)=CC=1.Cl>O.CN(C)C=O>[F:27][C:26]([F:29])([F:28])[CH2:25][S:14][C:11]1[CH:12]=[CH:13][C:8]([OH:7])=[CH:9][CH:10]=1
With stirring in an atmosphere of nitrogen, 110 g of anhydrous potassium carbonate was added to a solution composed of 51 g of 4-hydroxybenzenethiol and 250 ml of dimethylformamide. Furthermore, 112 g of 2,2,2-trifluoroethyl p-toluenesulfonate was added at a temperature of 25° to 30° C. The mixture was stirred at the same temperature for 3 hours, then at 30° to 40° C. for 4 hours, and finally at 50° C. for 6 hours. After cooling, the solution was poured into 2 liters of water, and concentrated hydrochloric acid was added at a temperature lower than 20° C. to adjust the pH of the solution to 3. The resulting oily product was extracted with toluene. The toluene layer was washed with water, and stirred together with 600 ml of a 10% aqueous solution of potassium hydroxide. The aqueous layer was separated, and hydrochloric acid was added at a temperature lower than 20° C. to adjust the pH of the aqueous layer to 2. The resulting oily product was extracted with toluene. The toluene layer was separated, washed with water, and then dried over anhydrous sodium sulfate. The toluene was evaporated, and the residue was distilled under reduced pressure to give 68 g of the desired 4-(2,2,2-trifluoroethylthio)phenol. b.p. 102°-105° C./0.8 mmHg.
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