Phosphorus tribromide → 2-Bromo-6-(bromomethyl)pyridine

To a solution of 2-bromo-6-(hydroxymethyl)pyridine (10.00 g, 53.2 mmol) in CH2Cl2 (150 mL) at 0° C. was added PBr3 (10.03 mL, 106 mmol) dropwise. The solution was allowed to warm to room temperature and stirred overnight. The reaction was quenched by adding saturated NaHCO3 dropwise while stirring. Solid K2CO3 was also added to attain a pH>7. The mixture was separated, and the aqueous layer was extracted with additional CH2Cl2. The combined organic layers were dried (MgSO4) and evaporated. The residue was purified by flash chromatography (0-20% ethyl acetate/hexanes) to afford the title compound as a colorless solid. LRMS (APCI) calc'd for C6H6Br2N [M+H]+: 250, Found: 250.

1. customThe reaction was quenched
2. additionby adding saturated NaHCO3 dropwise
3. stirringwhile stirring
4. additionSolid K2CO3 was also added
5. customThe mixture was separated
6. extractionthe aqueous layer was extracted with additional CH2Cl2
7. dry with materialThe combined organic layers were dried (MgSO4)
8. customevaporated
9. customThe residue was purified by flash chromatography (0-20% ethyl acetate/hexanes)

ORD record

ord-3bfe493630094737a6340f226626c42b

Source dataset

uspto-grants-2012_10

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08278335B2