Sodium Carbonate → 4-(Pyridin-3-yl)benzaldehyde

A mixture of 4-bromobenzaldehyde (2 g, 10.8 mmol), diethyl(3-pyridyl)borane (1.75 g, 11.9 mmol), tetrakis(triphenylphosphine)palladium (375 mg, 0.32 mmol), and 2N sodium carbonate aqueous solution(10.8 ml, 21.6 mmol) in toluene (40 ml) was heated under reflux under a nitrogen atmosphere overnight. The reaction mixture was allowed to return to room temperature and diluted with ethyl acetate. The mixture was washed with water and brine, and dried over sodium sulfate. After filtration, the filtrate was concentrated under reduced pressure, and the residue was purified by silica gel column chromatography (n-hexane/ethyl acetate=1/1) to afford 4-(pyridin-3-yl)benzaldehyde (1.43 g, yield 72%) as a pale yellow crystalline powder.

1. temperaturewas heated
2. temperatureunder reflux under a nitrogen atmosphere overnight
3. customto return to room temperature
4. washThe mixture was washed with water and brine
5. dry with materialdried over sodium sulfate
6. filtrationAfter filtration
7. concentrationthe filtrate was concentrated under reduced pressure
8. customthe residue was purified by silica gel column chromatography (n-hexane/ethyl acetate=1/1)

ORD-Eintrag

ord-6fca2443e6054be4a37a9e37ad4e5354

Quelldatensatz

uspto-grants-2007_08

DOI

10.6084/m9.figshare.5104873.v1

Patentnummer

US07262212B2