[Br-].[Cl:2][C:3]1[CH:21]=[CH:20][C:6]([C:7]([C:9]2[CH:19]=[CH:18][C:12]([CH2:13][S:14][C:15](N)=[NH2+])=[CH:11][CH:10]=2)=[O:8])=[CH:5][CH:4]=1.[C:22](=O)([O-])[O-].[K+].[K+].CO.[OH-].[K+]>C1(C)C=CC=CC=1.O>[Cl:2][C:3]1[CH:21]=[CH:20][C:6]([C:7]([C:9]2[CH:19]=[CH:18][C:12]([CH2:13][S:14][CH2:15][CH3:22])=[CH:11][CH:10]=2)=[O:8])=[CH:5][CH:4]=1
S-(4-(4-chlorobenzoyl)benzyl)thiouronium bromide (3.3 g) and potassium carbonate (1.5 g) were dissolved in dimethylformnamide (20 ml). A methanol solution (10 ml) of potassium hydroxide (1.0 g) was added and stirred at room temperature for 30 minutes. To the reaction mixture, water (100 ml) and toluene (100 ml) were added. The organic layer was separated, and washed with water and an aqueous saturated sodium chloride solution, followed by drying over anhydrous magnesium sulfate. After distilling off the solvent, the crude product was purified by silica gel column chromatography (developing solvent: ethyl acetaten:hexane=1:9) to obtain 4-chloro-4'-ethylmercaptomethylbenzophenone (1.3 g).
Loading…
