反应详情

A solution of chlorodimethylphosphine (250 mg, 2.60 mmol) in THF (0.7 mL) was added dropwise to a stirred suspension of sodium ethoxide (194 mg, 2.85 mmol) in THF (0.8 mL) at 0° C. The resulting mixture was stirred at room temperature for 30 min. then treated with 1-(bromomethyl)-3-nitrobenzene (560 mg, 2.59 mmol). The mixture was then stirred under nitrogen at 100° C. in a sealed tube for 2 h., concentrated in vacuo and the residue purified by chromatography over silica gel eluting with 5% MeOH in dichloromethane to afford 153 mg of dimethyl(3-nitrobenzyl)phosphane oxide (yield: 28%). 1H-NMR (CDCl3, 400 MHz): δ=1.53 (d, J=12.4 Hz, 6H), 3.27 (d, J=14.0 Hz, 2H), 7.55 (t, J=7.6 Hz, 1H), 7.71 (d, J=7.6 Hz, 1H), 8.11 (d, J=2.0 Hz, 1H), 8.16 (dd, J=0.8, 7.2 Hz, 1H). MS (ES+): m/z 214.00 (MH+). HPLC: tR=2.16 min (ZQ3, polar—5 min).

1. stirringThe mixture was then stirred under nitrogen at 100° C. in a sealed tube for 2 h.
2. concentrationconcentrated in vacuo
3. customthe residue purified by chromatography over silica gel eluting with 5% MeOH in dichloromethane