Bromine → Methyl 4-bromo-3-oxopentanoate

Participants

Reaction Steps

A solution of bromine (28.3 g, 0.177 mol) in chloroform (30 mL) was added dropwise over 2 h to a solution of methyl propionylacetate (23.5 g, 0.177 mol) in chloroform (155 mL) at 0-5° C. The mixture was stirred for 30 min, and the cooling bath was removed. The mixture was stirred for 18 h, and ice water (200 mL) was added. The organic layer was collected and washed with cold water (2×200 mL), 10% aqueous sodium thiosulfate (2×200 mL) and brine (200 mL). The filtered solution was dried (Na2SO4) and concentrated to 36.5 g of the title compound as a clear liquid.

Provenance & Evidence