[CH3:1][C:2]1[CH:7]=[CH:6][C:5]([SH:8])=[CH:4][CH:3]=1.[H-].[Na+].[F:11][C:12]([F:26])([F:25])[C:13]([CH3:24])([C:20]([F:23])([F:22])[F:21])[CH2:14]OS(C)(=O)=O>CN(C=O)C.[I-].C([N+](CCCC)(CCCC)CCCC)CCC.O>[CH3:1][C:2]1[CH:7]=[CH:6][C:5]([S:8][CH2:14][C:13]([CH3:24])([C:12]([F:11])([F:25])[F:26])[C:20]([F:23])([F:22])[F:21])=[CH:4][CH:3]=1
In a sealed tube dissolve 4-methylbenzenethiol (4.13 g, 33.2 mmol) in DMF (20 mL) at ambient temperature. Add portionwise with stirring sodium hydride (899 mg, 37.5 mmol) followed by tetrabutylammonium iodide (82 mg, 0.22 mmol) and a solution of methanesulfonic acid 3,3,3-trifluoro-2-methyl-2-trifluoromethylpropyl ester (6.16 g, 22.5 mmol) in DMF (10 mL). Stir at 150° C. overnight, cool the mixture to ambient temperature and dilute cautiously with water. Extract three times with EtOAc, dry over anhydrous Na2SO4, and concentrate in vacuo. Purify by chromatography on silica gel eluting with hexane to give the desired intermediate as a yellow oil (4.5 g, 62%).
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