Catalysis of the Abramov Reaction under Conditions of Microwave Activation

Abstract

Two series of α-hydroxyphosphonate synthesis according to the Abramov reaction are conducted under conditions of microwave activation. Acidic and basic catalysts are used along with 4-bromobenzaldehyde and 3-methoxy-4-hydroxybenzaldehyde. O,O-Diethylphosphite is used as a phosphorylating agent. The conversion of the reaction products is monitored via NMR spectroscopy. The optimum conditions for the synthesis of α-hydroxyphosphonates are selected. The crystal structure of reaction product O,O‑diethyl((4-bromophenyl(hydroxy)methyl)phosphonate 2, which crystallizes in the space group P21/n and is stabilized by multiple C–H⋅⋅⋅O and C–H⋅⋅⋅π interactions, is described for the first time.