[Br:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[S:8][C:9]1[CH:14]=[CH:13][C:12]([CH2:15][OH:16])=[CH:11][CH:10]=1.OO.[OH2:19].C(OCC)(=[O:22])C>C(O)(=O)C.[O-][W]([O-])(=O)=O.[Na+].[Na+]>[Br:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[S:8]([C:9]1[CH:14]=[CH:13][C:12]([CH2:15][OH:16])=[CH:11][CH:10]=1)(=[O:22])=[O:19]
To a solution of {4-[(2-bromophenyl)thio]phenyl}methanol (Step 2, 5.0 g, 16.9 mmol) in acetic acid (32 mL) was added hydrogen peroxide (4.2 mL, 50.8 mmol) and the reaction stirred overnight at room temperature. Further hydrogen peroxide (4.2 mL, 50.8 mmol) and catalytic sodium tungstate were added and the reaction stirred overnight. Water and ethyl acetate were added and the aqueous layer extracted with ethyl acetate (×2). The combined organic layers were washed with sodium hydrogen carbonate and brine, dried over MgSO4 and concentrated in vacuo. The residue was purified by flash column chromatography on silica, eluting with 60% ethyl acetate/isohexane, to give {4-[(2-bromophenyl)sulfonyl]phenyl}methanol as a white solid (4.0 g, 80%). δH (400 MHz, d6 DMSO): 8.31 (1H, dd, J=1.5, 7.9 Hz), 7.85 (2H, d, J=8.3 Hz), 7.79 (1H, d, J=7.9 Hz), 7.70 (1H, t, J=7.6 Hz), 7.60 (1H, td, J=1.0, 7.7 Hz), 7.54 (2H, d, J=8.3 Hz), 5.42 (1H, t, J=5.7 Hz), 4.57 (2H, d, J=5.4 Hz); m/z (ES+) 327, 329 [MH+].
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