Acetonitrile → 5-(4-Bromo-2-fluorophenyl)-2-methyloxazole

Participants

Reaction Steps

To a suspension of iodobenzene diacetate (6.7 g) in acetonitrile (100 mL) was added dropwise trifluoromethanesulfonic acid (3.7 mL), and the mixture was stirred at room temperature for 30 min. A mixture of 1-(4-bromo-2-fluorophenyl)ethanone (6.7 g) in acetonitrile (20 mL) was added to the reaction mixture, and the mixture was heated under reflux for 2 hr. The reaction mixture was allowed to cool to room temperature, and neutralized with saturated aqueous sodium hydrogen carbonate solution, and the solvent was evaporated under reduced pressure. The residue was extracted with ethyl acetate, the extract was washed with saturated brine and dried over anhydrous magnesium sulfate, and the solvent was evaporated under reduced pressure. The residue was purified by silica gel column chromatography (ethyl acetate/hexane) to give the title compound (2.6 g).

Provenance & Evidence