Hydrochloric Acid → 1,1′-(Oxydi-4,1-phenylene)bis[2-bromoethanone]

Participants

Reaction Conditions

Reaction Steps

Bromoacetyl chloride (2.22 ml, 22 mmol) was added dropwise during 15 min with stirring at −15° C. to a mixture of aluminum chloride (6.0 g, 44.8 mmol) in methylene dichloride (40 ml). The reaction mixture was stirred at −15° C. for an additional 3 min. Diphenyl ether (1.87 g, 11.0 mmol) was added during 30 min with stirring at −15° C. and the reaction mixture was allowed to warm to room temperature and then stirred for 3 h. It was then poured into a mixture of concentrated hydrochloric acid and crushed ice and extracted with methylene dichloride (2×50 ml). The combined organic extracts were washed with 2% aqueous sodium hydrogen carbonate and water and dried over Na2SO4. Evaporation of the solvent under reduced pressure gave desired product 50 3.03 g (67%).

Provenance & Evidence