HCID 16102910, compound → HCID 68454599, compound

Participants

Reaction Steps

To a solution of N-[(1E)-(4-bromo-2-fluorophenyl)methylidene]-2-methylpropane-2-sulfinamide (32.65 g, 0.1066 mol) in 550 mL CH2Cl2 at −48° C. was added methylmagnesium chloride (3.0 M solution is ether, 53.31 mL, 0.1599 mol) dropwise. The reaction was quenched with aqueous ammonium chloride and the aqueous layer was extracted with methylene chloride. The combined organics were dried over Na2SO4, filtered and concentrated under vacuum. The resulting residue was subjected to column chromatography on silica gel eluted with 10-50% ethyl acetate in hexanes to afford N-[(1R)-1-(4-bromo-2-fluorophenyl)ethyl]-2-methylpropane-2-sulfinamide as a white solid that gave proton NMR spectra consistent with theory and a mass ion (ES+) of 324.14 for M+H+ (81Br).

Provenance & Evidence