Reaktion #1572236

Reaktionsgleichung

3-bromo-6-(cyclopropyl)pyridine

4-formylphenylboronic acid

tripotassium phosphate

ethylene glycol

→

titled compound

Ausbeute 80.3%

4-(6-Cyclopropyl-3-pyridinyl)benzaldehyde

Ausbeute 80.3%

Lösungsmittel

ethyl acetate

water

Reaktionsbedingungen

Aufarbeitung

1. 1
   TemperaturAfter cooling the reaction mixture to room temperature
2. 2
   WaschenThe combined organic layers were washed with saturated brine
3. 3
   workup.DISTILLATIONbeing distilled off under reduced pressure
4. 4
   Sonstigewas purified by silica gel column chromatography (hexane:ethyl acetate=98:2-50:50)

Vorschrift

A mixture of 3-bromo-6-(cyclopropyl)pyridine (2.00 g), 4-formylphenylboronic acid (1.82 g), palladium(II) acetate (113 mg), tripotassium phosphate (4.50 g) and ethylene glycol (16.8 mL) was stirred at 80° C. for 3 hours. After cooling the reaction mixture to room temperature, water was added to it and two extractions were conducted with ethyl acetate. The combined organic layers were washed with saturated brine and thereafter the crude product was adsorbed on diatomaceous earth, with the solvent being distilled off under reduced pressure. The crude product adsorbed on the diatomaceous earth was purified by silica gel column chromatography (hexane:ethyl acetate=98:2-50:50) to give the titled compound as a colorless solid (1.81 g).

Quelle