Triethyl phosphite → Diethyl 3-Nitrobenzylphosphonate

Participants

Reaction Conditions

Reaction Steps

A mixture of 3-nitrobenzyl bromide (648 mg, 3.00 mmol) and triethyl phosphite (0.669 mL, 3.90 mmol) was stirred at 140° C. under nitrogen for 16 h. The excess triethyl phosphite was removed under reduced pressure and the residue purified by chromatography over silica gel eluting with 2% MeOH in dichloromethane to afford diethyl (3-nitrobenzyl)phosphonate, 0.80 g (yield: 98%). 1H-NMR (CD3OD, 400 MHz): δ=1.27 (t, J=6.8 Hz, 6 H), 3.43 (d, J=22.0 Hz, 2 H), 4.08 (q, J=6.8 Hz, 4 H), 7.58 (t, J=8.0 Hz, 1 H), 7.72 (d, J=7.6 Hz, 1 H), 8.15 (d, J=8.4 Hz, 1 H), 8.22 (d, J=2.4 Hz, 1 H). MS (ES+): m/z 273.99 (MH+). HPLC: tR=2.92 min (ZQ3, polar—5 min).

Provenance & Evidence