Bromine → Ethyl 3-bromo-2-oxocyclohexanecarboxylate

Participants

Reaction Steps

To a solution of ethyl 2-oxocyclohexanecarboxylate (50 g, 0.29 mol) in CHCl3 (150 mL) there was slowly added bromine (47 g, 0.29 mol) at 0° C. under a blanket of nitrogen as inert gas dropwise over a period of 45 minutes and the resultant mixture was stirred for a period of 6 hours at 0° C. and then for 16 hours at room temperature. Air was then passed into the reaction solution over a period of 2 hours. The organic phase was washed with aqueous saturated NaHCO3 solution (2×15 mL) and aqueous saturated NaCl solution (3×20 mL). Following drying of the organic phase over Na2SO4 and filtration, the solvent was removed. The product ethyl 3-bromo-2-oxocyclohexanecarboxylate was obtained in a yield of 72.6 g (corresponding to 99% of theory).

Provenance & Evidence