N-bromobutanimide → HCID 178525279, compound

Participants

Reaction Steps

To a solution of 6.0 g (35 mmoles) of 3-hydroxyisoxazol-5-ylacetic acid in 10 ml of N,N-dimethylformamide were added 6.5 g (42 mmoles) of N-bromosuccinimide, with ice-cooling and stirring. The mixture was stirred under ice-cooling for 2 hours and then at room temperature for 1 hour. The N,N-dimethylformamide was then distilled off under reduced pressure. The residue was dissolved in ethyl acetate and extracted with an aqueous solution of sodium hydrogen carbonate. The pH of the extract was adjusted to a value below 1.0 by the addition of concentrated hydrochloric acid, and then the solution was extracted with ethyl acetate. After drying the ethyl acetate extract, the solvent was distilled off. The crystals which formed the residue were recrystallized from a 1:5 by volume mixture of ethyl acetate and cyclohexane, giving 4.5 g (58%) of the title compound in the form of colourless plate crystals, melting point 167° C. with decomposition.

Provenance & Evidence