Sodium Carbonate → Diethyl (4-aminophenyl)phosphonate

Participants

Reaction Steps

(4-Nitro-phenyl)-phosphonic acid diethyl ester (7.6 g, 29.1 mmol) and SnCl2 (29.6 g, 0.13 mmol) were heated at reflux for 1 h. The mixture was poured in CH2Cl2 (500 mL) and adjusted to pH 8 with sat'd Na2CO3. The resulting mixture was filtered through Celite (CH2Cl2 wash) and the layers separated. The aqueous layer was extracted with CH2Cl2 and the combined extracts, were washed with water, sat'd NaCl, then dried over MgSO4 and filtered. Concentration yielded a light yellow solid (5.9 g, 88%): MS [M+H]+ 230; m.p. 117–118° C.

Provenance & Evidence