tert-Butylsulfinamide, (R)-(+)- → (R)-N-((4-fluoro-3-methoxyphenyl)(3-fluoro-5-(1,1,2,2-tetrafluoroethoxy)phenyl)methylene)-2-methylpropane-2-sulfinamide

Participants

Reaction Steps

To a solution of (4-fluoro-3-methoxyphenyl)(3-fluoro-5-(1,1,2,2-tetrafluoroethoxy)phenyl)methanone (16 g, 43 mmol) in THF (70 mL) was added Ti(OEt)4 (15 g, 65.9 mmol), followed by the addition of (R)-2-methylpropane-2-sulfinamide (5.86 g, 48.3 mmol). The reaction mixture was heated at reflux for 16 h, allowed to cool to room temperature and quenched by addition of saturated NaCl. The resulting mixture was filtered and the organic solvent was removed under reduced pressure. The residue was purified by ISCO chromatography using hexanes/EtOAc (10-50%) to afford (R)-N-((4-fluoro-3-methoxyphenyl)(3-fluoro-5-(1,1,2,2-tetrafluoroethoxy)phenyl)methylene)-2-methylpropane-2-sulfinamide as an oil (15 g, 75%). LCMS: RT=4.01 min, [M+H] 468.1 (Phenomenex Luna C18 column, 4.6×50 mm eluting with 10-90% MeOH/H2O over 4 minutes containing 0.1% TFA; 4 mL/min, monitoring at 220 nm).

Provenance & Evidence