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

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.

1. customDichloromethane was evaporated
2. additionWater (20 mL) was added
3. additionThe mixture was treated slowly with a saturated aqueous sodium bicarbonate solution
4. extractionThe mixture was extracted with dichloromethane (3×20 mL)
5. dry with materialdried over MgSO4
6. filtrationfiltered
7. customevaporated
8. customdried in vacuo

ORD record

ord-d604e400cee44f5eb792606b800df48e

Source dataset

uspto-grants-2016_04

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US09315521B2