4-Bromodiphenyl Ether → 1-(4-Phenoxyphenyl)propan-2-one

Participants

Reaction Steps

75.0 g of 4-bromodiphenyl ether, 129 ml of tributyltin methoxide, 45.0 g of isopropenyl acetate and 2,47 g of dichlorobis{tri(o-tolyl)phosphine}palladium, were dissolved in 300 ml of toluene and refluxed under heating for 3 hours. The reaction solution was left to cool to room temperature, and then, a saturated potassium fluoride aqueous solution was added, followed by stirring for one hour. Then, the product was subjected to celite filtration and washed with ethyl acetate. The filtrate and washing liquid were put together. Then, the organic layer was separated and washed with a saturated sodium chloride aqueous solution and then dried over anhydrous magnesium sulfate. The drying agent was filtered off, and then, the solvent was distilled off under reduced pressure. The residue was purified by silica gel column chromatography (hexane/ethyl acetate=15/1→10/1) to obtain 56.3 g (yield: 83%) of the above identified compound as yellow solid.

Provenance & Evidence