Diethyl Ether → 1-(2-Chlorophenyl)-2-(4-chlorophenyl)ethanone

Participants

Reaction Conditions

Reaction Steps

To a dried three-neck round bottom flask fitted with a condenser and addition funnel was added magnesium (2.217 g, 91.2 mmol) and anhydrous ether (60 mL). A solution of 4-chlorobenzyl bromide (18.74 g, 91.2 mmol) in ether (100 mL) was added dropwise via the addition funnel at room temperature. After the addition, the reaction mixture was heated at 34° C. for 1 hour. The reaction mixture was allowed to cool to room temperature. One half of the volume of the ether solution was then added to another dried flask charged with a solution of 2-chlorobenzonitrile (5.228 g, 38.0 mmol) in ether (70 mL). The resulting reaction mixture was stirred at 34° C. for 3 hours. The reaction was cooled to room temperature and quenched slowly with 2 M aq. HCl. The solution was diluted with ethyl acetate, and the organic portion was washed with 2N aq. HCl, water, dried (Na2SO4), filtered, and concentrated in vacuo. The crude product was purified by flash chromatography (silica gel) eluting with 7% ethyl acetate/hexane) to afford product.

Provenance & Evidence