3-Bromoanisole → 2-(3-Methoxyphenyl)cycloheptan-1-one

Participants

Reaction Steps

To a freshly prepared Grignard solution of 5.83 g of magnesium shavings and 28.7 ml of 1-bromo-3-methoxybenzene in 675 ml of anhydrous diethylether at 20° C., with stirring, were added first 20.95 g of copper(I) iodide, then dropwise a solution of 15.2 g of cyclohept-2-enone (80%) in 175 ml of anhydrous diethylether. After complete addition, the mixture was heated for 45 min under reflux. Then the product was decomposed by the dropwise addition of 85 ml of a saturated ammonium chloride solution. After diluting with 200 ml of water, the organic phase was separated and the aqueous phase was extracted twice using 100 ml of diethylether each time. The combined organic phases were washed once each with saturated solutions of sodium hydrogen carbonate and sodium chloride, dried over sodium sulfate and evaporated under vacuum. The residue was purified on a chromatography column using diethylether/n-hexane=1/4, finally 1/1, as eluant and 16.5 g (68.6% of theory) of the title compound was thus obtained as a pale yellow oil.

Provenance & Evidence