o-Fluorostyrene → 2-Chloro-1-[4,5-dihydro-5-(2-fluorophenyl)-3-isoxazolyl]ethanone

Participants

Reaction Conditions

Reaction Steps

To a suspension of 2-fluorostyrene (2.78 g, 22.8 mmol) and sodium bicarbonate (2.88 g, 34.2 mmol) in anhydrous toluene (15 mL) heated at 55° C. was added 3-chloro-N-hydroxy-2-oxo-propanimidoyl chloride (1.78 g, 11.4 mmol). After 2 h at 55° C., the reaction mixture was cooled, filtered, and the filtrate was concentrated under reduced pressure. The resulting residue was purified by column chromatography on silica gel using 10% ethyl acetate in hexanes as eluant to provide the title compound as a yellow solid (2.35 g) melting at 42-44° C.

Provenance & Evidence