Thionyl Chloride → 2-(Chloromethyl)-5-fluoropyridine

To a solution of (5-fluoro-pyridin-2-yl)-methanol (945 mg, 7.43 mmol) described in Manufacturing Example 41-1-1 in methylene chloride (70 mL) was added dropwise thionyl chloride (813 μL, 11.1 mmol) at room temperature, which was stirred for 30 minutes. This reaction solution was partitioned by addition of water, sodium hydrogencarbonate and methylene chloride. The organic layer was separated, washed with saturated aqueous sodium chloride, dried over anhydrous magnesium sulfate and filtered. The filtrate was concentrated under a reduced pressure. The residue was purified by NH silica gel column chromatography (hexane: diethyl ether=1:1) to obtain the title compound (761.1 mg, 70%).

1. customThis reaction solution was partitioned by addition of water, sodium hydrogencarbonate and methylene chloride
2. customThe organic layer was separated
3. washwashed with saturated aqueous sodium chloride
4. dry with materialdried over anhydrous magnesium sulfate
5. filtrationfiltered
6. concentrationThe filtrate was concentrated under a reduced pressure
7. customThe residue was purified by NH silica gel column chromatography (hexane: diethyl ether=1:1)

ORD record

ord-0cb2abe57e014cf59e0e9917f7390767

Source dataset

uspto-grants-2014_09

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08841327B2