Ethyl Acetate → 5-Chloro-2-(chloromethyl)pyridine

To a stirring solution of (5-chloropyridin-2-yl)methanol (840 mg, 5.8 mmol) in dichloromethane (10 mL) at 0° C. under argon was added thionyl chloride (0.64 mL, 8.77 mmol), followed by 4 drops of DMF (white precipitate formed). The reaction mixture was allowed to stir at room temperature for 1 h. The reaction mixture was concentrated to a white solid. The solid thus obtained was cooled in an ice bath before EtOAc (20 mL) and water (20 mL) and then 10% aqueous Na2CO3 solution (20 mL) were added. The organic layer was separated, washed with saturated aqueous NaCl, dried (MgSO4), filtered and concentrated to obtain 840 mg of the title compound as a light brown gum. HPLC/MS: retention time=2.392 min, [M+H]+=162.

1. concentrationThe reaction mixture was concentrated to a white solid
2. customThe solid thus obtained
3. customThe organic layer was separated
4. washwashed with saturated aqueous NaCl
5. dry with materialdried (MgSO4)
6. filtrationfiltered
7. concentrationconcentrated

ORD record

ord-9f8450a03e8f493db052c87b82442419

Source dataset

uspto-grants-2008_11

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07452892B2