Methyl formate → 3,5-Dichloro-4-pyridinecarboxaldehyde

To a solution of 3,5-dichloropyridine (296 mg, 2.0 mmol) in THF (6 mL), cooled to −78° C., under N2 protection, was added dropwise LDA (1.2 mL of a 1.8 M solution in THF, 2.2 mmol). After 30 min, a solution of formic acid methyl ester (240 mg, 4.0 mmol) in THF (1.0 mL) was added slowly to the solution. After 1.5 h, the reaction mixture was rapidly poured into a 0° C. sat. aqueous NaHCO3 solution. The aqueous layer was extracted with EtOAc and the organic layer was washed with water, brine, dried with MgSO4 and filtered. The solvent was removed under reduced pressure and the residue was purified by flash chromatography using heptane/EtOAc (5:1) as eluent to give 3,5-dichloro-pyridine-4-carbaldehyde as a white solid.

1. waitAfter 1.5 h
2. extractionThe aqueous layer was extracted with EtOAc
3. washthe organic layer was washed with water, brine
4. dry with materialdried with MgSO4
5. filtrationfiltered
6. customThe solvent was removed under reduced pressure
7. customthe residue was purified by flash chromatography

ORD record

ord-0d54bdf3daa24602906b2db7b8f15b44

Source dataset

uspto-grants-2012_07

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08222248B2