[F:1][CH2:2][C:3]([C:5]1[CH:10]=[CH:9][CH:8]=[C:7]([CH3:11])[C:6]=1[F:12])=O.[CH3:13][C:14]([S@:17]([NH2:19])=[O:18])([CH3:16])[CH3:15]>C1COCC1.[Cl-].[Na+].O.[O-]CC.[Ti+4].[O-]CC.[O-]CC.[O-]CC>[F:1][CH2:2]/[C:3](=[N:19]/[S@@:17]([C:14]([CH3:16])([CH3:15])[CH3:13])=[O:18])/[C:5]1[CH:10]=[CH:9][CH:8]=[C:7]([CH3:11])[C:6]=1[F:12]To a solution of 2-fluoro-1-(2-fluoro-3-methylphenyl)ethanone (5.03 g, 29.6 mmol) in THF (70 mL) were added (R)-2-methylpropane-2-sulfinamide (7.17 g, 59.1 mmol) and titanium (iv) ethoxide (15.30 ml, 73.9 mmol) and the resulting mixture was heated to reflux for 1.5 h. The reaction went to completion, brought to rt, and brine was added. The suspension was filtered, the filtrate was washed with brine, the organics extracts were combined, dried over Na2SO4, concentrated and chromatographed on silica gel using 0-30% EtOAc/hexanes to afford a light yellow oil as (R,E)-N-(2-fluoro-1-(2-fluoro-3-methylphenyl)ethylidene)-2-methylpropane-2-sulfinamide (4.71 g, 17.23 mmol, 58.3% yield). MS m/z=274 [M+H]+. Calculated for C13H17F2NOS: 273.10.
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