Reaktion #165335

Reaktionsgleichung

N,N-dimethylformamide

diethyl ether

2,5-dibromopyridine

n-butyl lithium

→

title compound

Ausbeute 66.0%

6-Bromo-pyridine-3-carbaldehyde

Ausbeute 66.0%

Lösungsmittel

Water

Reaktionsbedingungen

Aufarbeitung

1. 1
   workup.STIRRINGwas stirred for 35 minutes while the temperature
2. 2
   Temperaturwas raised to room temperature
3. 3
   Extraktionwhich was extracted with ethyl acetate
4. 4
   SonstigeThe organic layer was separated
5. 5
   Waschenwashed with saturated aqueous sodium chloride
6. 6
   Trocknendried over anhydrous magnesium sulfate
7. 7
   Filtrationfiltered
8. 8
   EinengenThe filtrate was concentrated under a reduced pressure
9. 9
   Sonstigethe residue was purified by silica gel column chromatography (heptane: ethyl acetate=3:1)

Vorschrift

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%).

Quelle