Dimethylformamide → 4-Bromo-2-(2-oxocyclopentyloxy)anisole

Participants

Reaction Conditions

Reaction Steps

A mixture of 5-bromo-2-methoxyphenol (6.31 g), α-chlorocyclopentanone (6.9 ml), potassium carbonate (9.57 g), and DMF (63 ml) was stirred at 90° C. for 2 hours. α-Chlorocyclopentanone (14 ml) was further added to the mixture, followed by stirring at 90° C. for one hour. After being allowed to stand for cooling, water was added to the mixture followed by extraction with ether. The organic layer was washed with a 1N aqueous solution of sodium hydroxide and then with a saturated saline, and dried over sodium sulfate. The solvent was distilled off, and the residue was purified by column chromatography (silica gel, hexane:ethyl acetate=2:1) to give Compound IIl-a (11.8 g, 99%) as an oily substance.

Provenance & Evidence