[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][C:9]=2[C:14]2[CH:19]=[CH:18][C:17](SC)=[CH:16][CH:15]=2)=[CH:4][CH:3]=1.Cl[C:23]1C=C(C=CC=1)C(OO)=O.[O-:33][S:34]([O-:36])=O.[Na+].[Na+]>C(Cl)Cl>[F:1][C:2]1[CH:3]=[CH:4][C:5]([C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][C:9]=2[C:14]2[CH:15]=[CH:16][C:17]([S:34]([CH3:23])(=[O:36])=[O:33])=[CH:18][CH:19]=2)=[CH:6][CH:7]=1To a stirred solution of 550 mg (1.9 mmol) of crude 1-(4-fluoro-phenyl)-2-[4-(methylthio)phenyl]benzene (Step 3) in 10 mL of methylene chloride at ambient temperature was slowly added 1.3 g (4.1 mmol) of 3-chloroperoxybenzoic acid (ca. 55%). Stirring was continued for 20 minutes prior to the addition of 1 g of Na2SO3. The reaction was allowed to stir for an additional 10 minutes and the solvent removed in vacuo. The residue was dissolved in ethyl acetate and the resulting solution washed twice with saturated NaHCO3 and dried over MgSO4. Recrystallization from ethyl acetate/hexane gave 437 mg (94%) of 1-(4-fluorophenyl)-2-[4-(methylsulfonyl)phenyl]benzene as a colorless solid: mp 178.0-179.0° C.; NMR (CDCl3) δ 3.05 (s, 3H), 6.93 (t, J=8 Hz, 2H), 7.03-7.09 (m, 2H), 7.32 (d, J=8 Hz, 2H), 7.38-7.50 (m, 4H), 7.80 (d, J=8 Hz, 2H). MS (FAB): m/e 333 (M+Li). Anal. Calc'd for C19 H15FO2S: C, 69.86; H, 4.60; F, 5.79. Found: c, 69.74; H, 4.72; F, 5.51.
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