Benzhydrol → Benzhydryl 4-bromo-3-oxobutyrate

Participants

Reaction Conditions

Reaction Steps

In 10.5 ml of methylene chloride there were dissolved 2.1 g of diketene, and at a temperature not exceeding -30° C., a solution of 4.0 g of bromine in 12.5 ml of methylene chloride was added dropwise to the solution with stirring. After the dropwise addition was completed, the mixture was maintained at 0° C. for 10 minutes. Separately, 3.68 g of benzhydrol were dissolved in 25 ml of methylene chloride, followed by addition of 2.02 g of triethylamine. Under stirring at a temperature not exceeding -30° C., the solution of bromoacetoacetyl bromide prepared above was added dropwise. After the dropwise addition, the mixture was stirred at 0° C. for 40 minutes, at the end of which time it was washed with water. After drying over magnesium sulfate the solvent was distilled off under reduced pressure, whereupon 6.99 g of benzhydryl 4-bromo-3-oxobutyrate there were obtained.

Provenance & Evidence