Diethyl Ether → 6-Bromo-3-pyridinecarboxaldehyde

Temperature

-78 °C

To a diethyl ether (60 mL) solution of 2,5-dibromopyridine (3.00 g, 12.7 mmol) was added n-butyl lithium (7.99 mL, 1.6 M hexane solution, 12.7 mmol) under nitrogen atmosphere at −78° C., which was stirred for 50 minutes at −78° C. Then, N,N-dimethylformamide (1.18 mL, 15.2 mmol) was added to the mixture, which was stirred for 35 minutes while the temperature was raised to room temperature. Water was added to the reaction solution at room temperature, which was extracted with ethyl acetate. 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, and the residue was purified by silica gel column chromatography (heptane: ethyl acetate=3:1) to obtain the title compound (1.56 g, 66%).

1. stirringwas stirred for 35 minutes while the temperature
2. temperaturewas raised to room temperature
3. extractionwhich was extracted with ethyl acetate
4. customThe organic layer was separated
5. washwashed with saturated aqueous sodium chloride
6. dry with materialdried over anhydrous magnesium sulfate
7. filtrationfiltered
8. concentrationThe filtrate was concentrated under a reduced pressure
9. customthe residue was purified by silica gel column chromatography (heptane: ethyl acetate=3:1)

ORD record

ord-4528474be8c64ba1bc6566e76eb69bf0

Source dataset

uspto-grants-2014_09

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08841327B2