Hydrochloric Acid → Diethyl 3-chloro-4-aminobenzylphosphonate

Participants

Reaction Steps

A solution of diethyl (3-chloro-4-nitrobenzyl)phosphonate (Compound 104C, 0.500 g, 1.62 mmol) in EtOH (10 mL) was charged with iron (0.454 g, 8.12 mmol) and heated to reflux. When the reaction mixture reached reflux, it was charged with 0.1 N aq HCl (0.500 mL, 0.0812 mmol) and stirred for 10 min. The reaction mixture was filtered through a pad of celite and the filtrate was concentrated in vacuo. The compound was purified on an Isco Combiflash eluting with 40 to 90% EtOAc in heptane to afford the title compound. 1H NMR (400 MHz, chloroform-d) δ 7.19 (t, J=2.40 Hz, 1H), 7.01 (td, J=2.27, 8.08 Hz, 1H), 6.71 (dd, J=0.63, 8.21 Hz, 1H), 3.96-4.08 (m, 4H), 2.96-3.06 (m, 2H), 1.26 (t, J=7.07 Hz, 6H); MS (ES+): m/z: 278.0633 [MH+]. HPLC: tR=1.18 min (UPLC TOF MS: polar—3 min).

Provenance & Evidence