HCID 12171907, compound → HCID 86668957, compound

Participants

Reaction Steps

To a solution of 2.8 g (9.7 mmol) N-[(1E)-(4-bromophenyl)methylidene]-2-methylpropane-2-sulfinamide in 30 ml CH2Cl2 at −78° C. was added 49 mL (24 mmol) 0.5M bromo(ethynyl)magnesium in THF. The reaction mixture was warmed slowly to room temperature. After 24 h at room temperature, the reaction mixture was quenched with saturated ammonium chloride, extracted three times with methylene chloride, and washed with brine. The organic layer was dried over NaSO4, filtered and concentrated in vacuo. Purification by flash chromatography (silica gel, linear gradient 0-100% EtOAc:hexane) afforded N-[(1R)-1-(4-bromophenyl)prop-2-ynyl]-2-methylpropane-2-sulfinamide. 1H NMR (CDCl3, 400 MHz) 7.52-7.45 (m, 2H); 7.41-7.38 (m, 2H); 5.19 (dd, 1H, J=2.38 Hz, 6.05 Hz); 3.66 (br d, 1H, J=6.04 Hz); 2.64 (d, 1H, J=2.38 Hz); 1.20 (s, 9H). ESMS+1=316.0.

Provenance & Evidence