Thionyl Chloride → 5-bromo-2-(chloromethyl)pyridine

To the stirred solution of (5-Bromo-pyridin-2-yl)-Methanol (5 gm, 26.59 mmol, 1 eq) in DCM (50 mL) at 0° C. is added Thionyl chloride (3 mL) drop wise at RT then stirred at RT for 4 h. After completion, the reaction mixture quenched with saturated sodium bicarbonate solution and extracted with DCM (3×100 mL). The combined organic layer dried over sodium sulphate and evaporated under reduced pressure. The crude is purified by column chromatography using silica 100-200 mesh using 10% EtOAc: Hexane as eluent to afford title compound (4 g) as brown colored liquid. 1NMR (400 MHz, DMSO) δ: 4.77 (s, 2H), 7.54 (d, J=8.64 Hz, 1H), 8.09-8.12 (dd, J1=2.4 Hz, J2=8.32 Hz, 1H), 8.70 (d, J=5.96 Hz, 1H).

1. customAfter completion, the reaction mixture quenched with saturated sodium bicarbonate solution
2. extractionextracted with DCM (3×100 mL)
3. dry with materialThe combined organic layer dried over sodium sulphate
4. customevaporated under reduced pressure
5. customThe crude is purified by column chromatography

ORD record

ord-4ad77ac305b04f4bb2a6f57d38bed8e0

Source dataset

uspto-grants-2016_08

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US09422236B2