Boron tribromide → HCID 67606759, compound

Participants

Reaction Conditions

Reaction Steps

4-Bromo-1-(cyclopropylmethyl)-5-methoxy-1H-benzotriazole (8.0 g, 28 mmol) was dissolved in dichloromethane (200 mL), cooled to 0° C. and treated with boron tribromide (57 mL, 1 M dichloromethane solution, 57 mmol, 2 equiv). The ice bath was removed and the mixture was warmed to ambient temperature and stirred for 4 hours. The mixture was treated slowly with water (exotherm), the pH of the solution was adjusted to pH>10 with 1 N aqueous sodium hydroxide and stirred for an additional 30 minutes. The pH of the mixture was then adjusted to pH 6-7 with ammonium chloride (aqueous saturated) and extracted exhaustively with dichloromethane containing 5% methanol. The combined organic extracts were dried with sodium sulfate, filtered and concentrated in vacuo, providing the titled compound.

Provenance & Evidence