2-Bromobenzaldehyde → Methyl 2-azido-3-(2-bromophenyl)prop-2-enoate

Participants

Reaction Steps

A solution of 75 ml (624 mmol) of 2-bromobenzaldehyde and of 252 g (2.2 mmol) of methyl azidoacetate in 160 ml of methanol is added dropwise over 3 h, at a temperature of −10 to −8° C., under nitrogen and with mechanical stirring, to a solution of 476 ml of sodium methoxide (30% in methanol) in 950 ml of methanol. Stirring is maintained for 2 h at a temperature below 5° C. The mixture is poured onto 1.5 kg of ice. The precipitate is collected by filtration, washed with water and dried under reduced pressure with light excluded. 116 g (0.41 mol) of solid are obtained, which solid is used quickly in the following stage.

Provenance & Evidence