Boron tribromide → HCID 68657033, compound

Participants

Reaction Conditions

Reaction Steps

4-Chloro-1-(cyclopropylmethyl)-5-methoxy-1H-benzotriazole (8-4, 10.5 g, 44.2 mmol) was dissolved in dichloromethane (200 mL), cooled to 0° C. and treated with boron tribromide (88 mL, 1M dichloromethane solution, 88 mmol, 2 equiv). The ice bath was removed and the mixture was stirred for 4 hours at ambient temperature. The mixture was slowly treated with water (10 mL) and then treated with sodium hydroxide ON aqueous) until pH>10. After stirring for an additional 30 minutes, ammonium chloride (aqueous saturated) was added until the pH of the mixture was adjusted to pH 6-7. The aqueous mixture was exhaustively extracted with dichloromethane containing 5% methanol. The combined organic extracts were dried with sodium sulfate, filtered and concentrated in vacuo, providing the titled compound 8-5 as a light brown solid.

Provenance & Evidence