Diphenyl Ether → HCID 19612125, compound

Participants

Reaction Conditions

Reaction Steps

A mixture of 3.31 g (0.038 mol) of bromoacetyl bromide, 50 ml of methylene chloride and 5 g (0.029 mol) of diphenyl ether is cooled to 0-5° C. and 4.42 ml (0.033 mol) of aluminum chloride are added. The mixture is stirred at room temperature for 4 hours. It is poured into a-water/ice mixture, the two phases are separated and the organic phase is washed with 1 N hydrochloric acid and with water. The organic phase is dried over sodium sulfate and the solvent is evaporated off under reduced pressure. The residue is purified by chromatography on a silica gel column using a 7/3 cyclohexane/ethyl acetate mixture as the eluent. The fraction of the medium corresponding to 3.2 g of 2-(4-phenoxyphenyl)acetyl bromide is isolated. The resulting oil is mixed with 5.9 ml (0.077 mol) of trifluoroacetic acid and 7.7 ml (0.048 mol) of triethylsilane. The mixture is heated at 80° C. for 4 hours and the residue is taken up with an ethyl ether/sodium bicarbonate mixture. The two phases are separated, the organic phase is dried over sodium sulfate and the solvent is evaporated off under reduced pressure to give 7 g of the title compound.

Provenance & Evidence