Dimethylformamide → 6-Bromo-3-pyridinecarboxaldehyde

Temperature

-78 °C

2,5-Dibromopyridine (5.4 g) was stirred in diethyl ether (100 ml) under a nitrogen atmosphere, the solution was cooled at −78° C., then n-butyllithium (2.66M solution in hexane) (8.5 ml) was added dropwise thereto followed by stirring for 20 minutes, then N,N-dimethylformamide (4.0 ml) was added dropwise thereto followed by stirring for 10 minutes. A saturated aqueous solution of ammonium chloride and water were sequentially added thereto followed by stirring, the solution was extracted with ethyl acetate, then sequentially washed with water and brine, dried over anhydrous magnesium sulfate, and then the solvent was evaporated in vacuo. The residue was purified by silica gel column chromatography (hexane-ethyl acetate system) to provide the title compound (2.2 g).

1. stirringby stirring for 10 minutes
2. stirringby stirring
3. extractionthe solution was extracted with ethyl acetate
4. washsequentially washed with water and brine
5. dry with materialdried over anhydrous magnesium sulfate
6. customthe solvent was evaporated in vacuo
7. customThe residue was purified by silica gel column chromatography (hexane-ethyl acetate system)

ORD record

ord-09ed0fff836548e1b4e01776fb55ff95

Source dataset

uspto-grants-2013_03

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08399520B2