Hydrochloric Acid → 9-[5-(4-Bromo-2-fluorophenoxy)-2-ethylphenyl]-3-oxaspiro[5.5]undecane-8,10-dione

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Reaction Steps

A mixture of 9-(5-bromo-2-ethylphenyl)-3-oxaspiro[5.5]undecane-8,10-dione (360 mg, 0.99 mmol), 4-bromo-2-fluorophenol (227 mg, 1.19 mmol), cesium carbonate (645 mg, 1.98 mmol), copper(II) trifluoromethanesulfonate (18 mg, 0.05 mmol) and ethyl acetate (50 μl) in toluene (10 ml) is heated under reflux for 19 hours. The mixture is cooled to room temperature, N,N-dimethylformamide (2 ml) and 2M aqueous hydrochloric acid (10 ml) are added, and the mixture is stirred vigorously for 45 minutes. The mixture is extracted with ethyl acetate, and the organic extract is dried over anhydrous magnesium sulfate, filtered and the filtrate is evaporated under reduced pressure. The residue is purified by preparative reverse phase HPLC to give 9-[5-(4-bromo-2-fluorophenoxy)-2-ethylphenyl]-3-oxaspiro[5.5]undecane-8,10-dione.

Provenance & Evidence