Potassium Phosphate, Tribasic → Tert-butyl 4-[cyano(diethoxyphosphoryl)methyl]benzoate

Participants

Reaction Conditions

Reaction Steps

Diethyl cyanomethylphosphonate (0.35 ml, 2.164 mmol), tert-butyl 4-bromobenzoate (0.5096 g, 1.982 mmol), bis(tri-t-butylphosphine)palladium (0.051 g, 0.099 mmol), potassium phosphate, tribasic (1.2381 g, 5.83 mmol) and toluene (6 ml) were combined in a flask. Nitrogen was bubbled through the reaction for approximately two minutes to deoxygenate the reaction. The reaction was allowed to heat at 100° C. until complete (3-24 h). The reaction was filtered over celite. The resulting material was partially purified by column chromatography on silica gel. The partially purified material was further purified by HPLC. 1H NMR (CDCl3, 600 MHz) δ 8.01 (d, J=6 Hz, 2H), 7.52 (d, J=6.9 Hz, 2H), 4.30 (d, JP-H=26.4 Hz, 1H), 4.19-4.01 (m, 4H), 1.59 (s, 9H), 1.32 (m, 3H), 1.26 (m, 3H). MS: cal'd 354 (MH+), exp 354 (MH+).

Provenance & Evidence