Isopropanol → Dipropan-2-yl(4-nitrophenyl)phosphonate

Participants

Reaction Steps

A solution of distilled dry propan-2-ol (20 ml) and triethylamine (1.0 g, 10 mmol) was added dropwise to (4-nitrophenyl)phosphonic dichloride (1.2 g, 5 mmol) at 0° C. The resulting mixture was stirred at reflux overnight, the mixture filtered and the filtrate concentrated under reduced pressure to yield a crude product, which was purified by chromatography over silica gel eluting with petroleum ether:EtOAc: 5:1 to afford 360 mg of desired dipropan-2-yl(4-nitrophenyl)phosphonate (yield: 25%). 1H-NMR (CDCl3, 400 MHz): δ=1.18 (d, J=6.0 Hz, 6H), 1.33 (d, J=6.4 Hz, 6H), 4.65-4.73 (m, 2H), 7.93 (dd, J=8.8, 12.8 Hz, 2H), 8.22 (dd, J=3.2, 8.8 Hz, 2H).

Provenance & Evidence