Diethyl Ether → 2-Fluoro-1-phenylethan-1-one

Participants

Reaction Conditions

Reaction Steps

A mixture of 2-bromoacetophenone (20.00 gm, 100 mmol) and KF (8.82 gm, 152 mmol) in dry DMF (35 ml) was heated at 100° C. for 1 hour. Additional KF (2.26 gm) was added and heating of the mixture continued for 4 more hours. The dark-red solution was cooled, poured into Et2O and washed with H2O (twice) and brine. The ethereal solution was dried (Na2SO4), filtered, and stripped to yield a dark red oil. The oil was distilled to collect a fraction boiling between 62°-64° C. at 1 mm Hg which was 91 molar percent the title compound and 9 molar percent acetophenone (6.00 gm). Flash chromatography (Merck SiO2, 10% EtOAc in hexane) afforded the pure title compound (5.50 gm, 45%) as a liquid that solidifies near room temperature.

Provenance & Evidence