ClC1C=C(C=CC=1)C(OO)=[O:6].[F:12][C:13]([S:16][C:17]1[CH:18]=[CH:19][C:20]2[O:24][CH:23]=[N:22][C:21]=2[CH:25]=1)([F:15])[F:14].C(=O)(O)[O-].[Na+].S([O-])([O-])(=O)=S.[Na+].[Na+]>C(Cl)(Cl)Cl>[F:15][C:13]([F:12])([F:14])[S:16]([C:17]1[CH:18]=[CH:19][C:20]2[O:24][CH:23]=[N:22][C:21]=2[CH:25]=1)=[O:6]
0.71 g of 3-chloroperoxybenzoic acid (purity of 65% or more) was added to a mixture of 0.50 g of 5-trifluoromethylsulfanylbenzoxazole and 3 ml of chloroform under ice cooling, and then the mixture was stirred at room temperature for 1 day. A saturated aqueous sodium bicarbonate solution and a saturated aqueous sodium thiosulfate solution were added to the reaction mixture, and the mixture was extracted with ethyl acetate. The organic layer was dried over anhydrous sodium sulfate and then concentrated under reduced pressure. The resulting residue was applied to a silica gel column chromatography to obtain 0.20 g of 5-trifluoromethylsulfinylbenzoxazole.
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