Phosphorus tribromide → 3-(Bromomethyl)-2-chloropyridine

Participants

Reaction Steps

To a solution of (2-chloropyridin-3-yl)methanol (800 mg, 5.6 mmol) in anhydrous dichloromethane (50 mL) was added dropwise phosphorus tribromide (1.0 mL, 11.2 mmol). The mixture was stirred at room temperature overnight. Dichloromethane was evaporated. Water (20 mL) was added. The mixture was treated slowly with a saturated aqueous sodium bicarbonate solution. The mixture was extracted with dichloromethane (3×20 mL). The organic extracts were combined, dried over MgSO4, filtered, evaporated, and dried in vacuo, affording 3-(bromomethyl)-2-chloropyridine (1.0 g, 80% yield). The product was used without further purification.

Provenance & Evidence