Methanol → Methyl 2-bromo-3-methoxypropanoate

Participants

Reaction Steps

480 g of mercuric acetate was added to a solution of 139 g of methyl acrylate in 170 ml of methanol. The resulting mixture was stirred for 3 days at room temperature. To the mixture, cooled in an ice bath, a solution of 100 g of potassium bromide in 600 ml of water was added. A heavy oil formed, was separated from the mixture and was extracted with chloroform. The extract was washed with water, dried (MgSO4) and filtered. The filtrate was heated to 60° C. and 36.9 g of bromine was added, drop-by-drop over a 2-hour period. The resulting mixture was cooled to 5° C. and concentrated in a rotary evaporator. The liquid residue was distilled to give methyl 2-bromo-3-methoxypropionate (5A), b.p.: 69-72° C. (3-5 Torr.).

Provenance & Evidence