Diethyl Ether → 1-(3,4-Dichlorophenyl)-2-methoxyethanone

Participants

Reaction Steps

A solution (about 100 mL) of 3,4-dichlorophenylmagnesium bromide in diethyl ether was prepared from a mixture of magnesium (flakes) (2.07 g) in diethyl ether (100 mL) and 1-bromo-3,4-dichlorobenzene (17.5 g). A solution of methoxyacetonitrile (5.0 g) in diethyl ether (10 mL) was added dropwise to a solution of 3,4-dichlorophenylmagnesium bromide in diethyl ether under ice-cooling, and the resulting mixture was stirred under ice-cooling for 20 min. The reaction mixture was quenched with water, the mixture was acidified with 1 N hydrochloric acid, and the mixture was stirred under ice-cooling for 15 min. The reaction mixture was extracted with ethyl acetate, the organic layer was washed with water and brine, and dried over anhydrous magnesium sulfate, and the solvent was evaporated to give a pale-yellow oil. The oil was purified by silica gel column chromatography (eluent; hexane:ethyl acetate (19:1-1:1)) to give the title compound (10.5 g).

Provenance & Evidence