Epibromohydrin → HCID 19020732, compound

Participants

Reaction Steps

29.6 g (0.153 moles) of sodium methoxide (as a 28% w/v methanolic solution) were added to a solution of 30.0 g (0.153 moles) of 5-(m-chlorophenyl)-3-hydroxyisoxazole in 300 ml of dimethylformamide, and the mixture was stirred at room temperature for 30 minutes. At the end of this time, 41.9 g (0.306 moles) of epibromohydrin were added dropwise, and the mixture was stirred for a further 3 days. The reaction mixture was then concentrated by evaporation under reduced pressure, and the residue was diluted with ethyl acetate. The resulting mixture was washed with 800 ml of a 10% w/v aqueous solution of sodium chloride. The organic layer was then dried over anhydrous magnesium sulfate, the desiccant was removed by filtration, and the solvent was removed by distillation under reduced pressure. The residue was purified by column chromatography through silica gel, eluted with a 2:1 by volume mixture of benzene and ethyl acetate, to give a solid residue, which was recrystallized from diisopropyl ether, to give 23.6 g (yield 73.5%) of the title compound as colorless needles, melting at 86°-87° C.

Provenance & Evidence