[F:1][C:2]1[CH:7]=[CH:6][C:5]([SH:8])=[CH:4][CH:3]=1.[OH-:9].[Na+].I[CH2:12][CH2:13][CH3:14].ClC1C=CC=C(C(OO)=[O:23])C=1>CO.O.C(Cl)Cl>[F:1][C:2]1[CH:7]=[CH:6][C:5]([S:8]([CH2:12][CH2:13][CH3:14])(=[O:23])=[O:9])=[CH:4][CH:3]=1A cooled (0° C.) solution of 4-fluorothiophenol (Merck Kgaa; 2.00 g; 15.6 mmol) in MeOH (40 ml) was treated with a 5 N solution of NaOH in water (3.28 ml) and 1-iodopropane (1.67 ml; 17.2 mmol). The reaction mixture was stirred at RT for 1 hour, the mixture was concentrated under reduced pressure, the residue taken up in EtOAc and washed with brine, dried on MgSO4, filtered and concentrated under reduced pressure. The intermediate thus obtained was dissolved in DCM (50 ml) and treated with 3-chloroperbenzoic acid (8.46 g; 34.33 mmol) and stirred at RT for 3 hours. The solvent was removed under reduced pressure, the residue taken up in EtOAc and washed with brine, dried on MgSO4, filtered and concentrated under reduced pressure to afford the title compound (2.75 g, 87%).
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