Sulfuric Acid → Ethyl 4-bromo-3-oxocyclohexanecarboxylate

Participants

Reaction Steps

To a solution of ethyl 4-bromo-3-hydroxycyclohexanecarboxylate (15.06 g) in acetone (300 mL) at 0° C. was added CrO3 (12.0 g, 120 mmol), and 2 N H2SO4 (60 mL). The mixture was stirred at room temperature for 30 min. Isopropanol (15 mL) was added and the reaction was stirred for 20 min. The volume was reduced under vacuum then diluted with water and extracted with ethyl acetate. The organic layer was washed with water, then brine, was dried over MgSO4 and concentrated in vacuo. Purification by chromatography on silica gel (10% EtOAc in hexane) afforded 6.7 g of tide compound.

Provenance & Evidence