Boron trifluoride etherate → 8-Benzyloxy-5-(2-bromoacetyl)-2-hydroxyquinoline

Participants

Reaction Steps

A solution of 7.8 g of bromine in 30 ml of methylene chloride is added dropwise to a refluxing solution of 13 g of 5-acetyl-8-benzyloxycarbostyril and 7.56 g of boron trifluoride etherate in 170 ml of methylene chloride, and the mixture is refluxed for 30 minutes under heating. The mixture is concentrated under reduced pressure to remove solvent. The residue is made alkaline with an aqueous 10% potassium carbonate solution, and the resultant precipitates are collected by filtration. The crystals are recrystallized from a mixture of chloroform and methanol. 12.51 g of 5-bromoacetyl-8-benzyloxycarbostyril are obtained as pale yellow needles. Yield: 75.7%

Provenance & Evidence