Triisopropyl phosphite → Dipropan-2-yl [(4-nitrophenyl)methyl]phosphonate

Participants

Reaction Steps

A mixture of 4-nitrobenzylbromide (15.0 g) and triisopropyl phosphite (15.9 g) was stirred for 3 hr while heating under reflux. The reaction mixture was subjected to silica gel column chromatography, and diisopropyl 4-nitrobenzylphosphonate (19.5 g) was obtained as an oil from a fraction eluted with ethyl acetate-chloroform (1:1, volume ratio). A mixture of this oil, 5% palladium-carbon (2.3 g) and ethanol (130 ml) was stirred at room temperature for 6 hr under a hydrogen atmosphere. The catalyst was filtered off and the filtrate (ethanol solution) was concentrated to give diisopropyl 4-aminobenzylphosphonate (17.2 g, yield 98%) as a yellow oil.

Provenance & Evidence