Reaktion #2320134

Reaktionsgleichung

2-(3-bromophenyl)-5-methylpyridine

3-fluorophenylboronic acid

triphenylphosphine

sodium carbonate

→

2-(3′-fluorobiphenyl-3-yl)pyridine

Lösungsmittel

water

dimethoxyethane

ethyl acetate

Reaktionsbedingungen

Aufarbeitung

1. 1
   Sonstigethree-necked round bottom flask equipped with a stir bar
2. 2
   TemperaturThe solution was heated
3. 3
   Temperaturat reflux for twenty hours
4. 4
   Temperaturcooled
5. 5
   SonstigeThe organic layer was separated
6. 6
   Trocknendried over magnesium sulfate
7. 7
   Sonstigeevaporated to dryness
8. 8
   Sonstigeto give a brown liquid, which
9. 9
   Sonstigewas purified by flash silica gel chromatography
10. 10
    Sonstigeyielding a viscous, colorless liquid (12.5 g 80%)

Vorschrift

To a 500 mL. three-necked round bottom flask equipped with a stir bar, temperature probe, and a nitrogen inlet were added 2-(3-bromophenyl)-5-methylpyridine (14.7 g, 60 mmol), 3-fluorophenylboronic acid (10.0 g, 72 mmol), palladium (II) acetate (0.335 g, 1.5 mmol), triphenylphosphine (1.56 g, 6.0 mmol), sodium carbonate (17.0 g, 160 mmol), containing dimethoxyethane (120 mL.) and water (80 mL.). The solution was heated at reflux for twenty hours, cooled, and diluted with ethyl acetate. The organic layer was separated, dried over magnesium sulfate, and evaporated to dryness to give a brown liquid, which was purified by flash silica gel chromatography using a 5/95 to 10/90 ethyl acetate/hexane gradient, yielding a viscous, colorless liquid (12.5 g 80%).

Quelle