(NE)-N-[(4-bromophenyl)methylidene]-2-methylpropane-2-sulfinamide

反応条件: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

実験手順: 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. the reaction mixture was quenched with saturated ammonium chloride extracted three times with methylene chloride washed with brine The organic layer was dried over NaSO4 filtered concentrated in vacuo Purification by flash chromatography (silica gel, linear gradient 0-100% EtOAc:hexane)

反応条件: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

実験手順: To a solution of 2.0 g (10 mmol) 4-bromobenzaldehyde in 20 ml CH2Cl2 at rt was added 1.3 g (10 mmol) (S)-(−)-2-methylpropane-2-sulfinamide and 2.4 g (10 mmol) copper (II) sulfate. After 24 h at room temperature, the reaction mixture was filtered through celite and concentrated in vacuo. Purification by flash chromatography (silica gel, linear gradient 0-40% EtOAc:hexane) afforded 2.8 g (90%) N-[(1E)-(4-bromophenyl)methylidene]-2-methylpropane-2-sulfinamide. ES-MS [M+1]=289.0. the reaction mixture was filtered through celite and concentrated in vacuo Purification by flash chromatography (silica gel, linear gradient 0-40% EtOAc:hexane)

反応条件: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

実験手順: To a solution of 2.0 g (10 mmol) 4-bromobenzaldehyde in 20 ml CH2Cl2 at rt was added 1.3 g (10 mmol) (S)-(−)-2-methylpropane-2-sulfinamide and 2.4 g (10 mmol) copper (II) sulfate. After 24 h at room temperature, the reaction mixture was filtered through celite and concentrated in vacuo. Purification by flash chromatography (silica gel, linear gradient 0-40% EtOAc:hexane) afforded 2.8 g (90%) N-[(1E)-(4-bromophenyl)methylidene]-2-methylpropane-2-sulfinamide. ES-MS [M+1]=289.0. the reaction mixture was filtered through celite and concentrated in vacuo Purification by flash chromatography (silica gel, linear gradient 0-40% EtOAc:hexane)

反応条件: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

実験手順: 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. the reaction mixture was quenched with saturated ammonium chloride extracted three times with methylene chloride washed with brine The organic layer was dried over NaSO4 filtered concentrated in vacuo Purification by flash chromatography (silica gel, linear gradient 0-100% EtOAc:hexane)

反応条件: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

実験手順: To a solution of 2.0 g (10 mmol) 4-bromobenzaldehyde in 20 ml CH2Cl2 at rt was added 1.3 g (10 mmol) (S)-(−)-2-methylpropane-2-sulfinamide and 2.4 g (10 mmol) copper (II) sulfate. After 24 h at room temperature, the reaction mixture was filtered through celite and concentrated in vacuo. Purification by flash chromatography (silica gel, linear gradient 0-40% EtOAc:hexane) afforded 2.8 g (90%) N-[(1E)-(4-bromophenyl)methylidene]-2-methylpropane-2-sulfinamide. ES-MS [M+1]=289.0. the reaction mixture was filtered through celite and concentrated in vacuo Purification by flash chromatography (silica gel, linear gradient 0-40% EtOAc:hexane)