Triethyl phosphite → Diethyl (3-methoxy-4-nitrobenzyl)phosphonate

Participants

Reaction Conditions

Reaction Steps

In a sealed tube, a mixture of 4-(bromomethyl)-2-methoxy-1-nitrobenzene (4.22 g, 17.2 mmol) and triethyl phosphite (3.5 g, 21 mmol) was heated to 100° C. for 16 h. The reaction was cooled to ambient temperature, transferred to a round bottom flask, and concentrated in vacuo. The crude oil was adsorbed onto a pre-filled solid loading cartridge [RediSepRf 25 gram] and purified using the Teledyne/ISCO system [RediSepRf Silica 40 gram], eluting with 0-5% MeOH:CH2Cl2. The desired fractions were combined and concentrated in vacuo, affording the title material as a yellow oil, 5.0439 g (87%, 14.970 mmol). 1H NMR (CDCl3) δ ppm 7.83 (dd, J=8.2, 0.9 Hz, 1H), 7.08 (t, J=1.9 Hz, 1H), 6.94 (dt, J=8.3, 2.0 Hz, 1H), 4.07 (ddd, J=8.3, 7.1, 1.3 Hz, 4H), 3.97 (s, 3H), 3.14-3.25 (m, 2H), 1.29 (t, J=7.1 Hz, 6H). MS (ES+): m/z 304.00 (100) [MH+]. HPLC: tR=2.89 min (ZQ3, polar—5 min).

Provenance & Evidence