Reaktion #2320126

Reaktionsgleichung

2-(3-bromophenyl)-5-methylpyridine

phenylboronic acid

triphenylphosphine

potassium carbonate

→

2-biphenyl-3-yl-5-methylpyridine

Ausbeute 91.6%

Lösungsmittel

ethyl acetate

water

ethylene glycol dimethyl ether

Reaktionsbedingungen

Aufarbeitung

1. 1
   Sonstigeequipped with a temperature probe
2. 2
   Temperaturreflux condenser, and a magnetic stir bar
3. 3
   TemperaturThe solution was then heated
4. 4
   Temperaturat reflux under nitrogen for 16 hr
5. 5
   SonstigeThe cooled reaction mixture
6. 6
   Sonstigewas placed in a separatory funnel
7. 7
   ExtraktionThe organic layer was extracted twice with a saturated solution of sodium chloride
8. 8
   Trocknendried over magnesium sulfate
9. 9
   Sonstigeevaporated to dryness
10. 10
    SonstigeAfter the removal of several impurities
11. 11
    workup.DISTILLATIONby vacuum distillation at 115° C.
12. 12
    workup.DISTILLATIONdistillation at 190° C.

Vorschrift

2-(3-bromophenyl)-5-methylpyridine (14.0 g, 61 mmol), phenylboronic acid (8.8 g, 72 mmol), palladium (II) acetate (0.34 g, 1.5 mmol), triphenylphosphine (1.6 g, 6.1 mmol), and potassium carbonate (22.3 g, 162 mmol) were mixed with 120 mL of ethylene glycol dimethyl ether and 80 mL of water in a 500 mL round bottom flask equipped with a temperature probe, reflux condenser, and a magnetic stir bar. The solution was then heated at reflux under nitrogen for 16 hr. The cooled reaction mixture was placed in a separatory funnel, and 100 mL of ethyl acetate was added. The aqueous layer was discarded. The organic layer was extracted twice with a saturated solution of sodium chloride, dried over magnesium sulfate, and evaporated to dryness. After the removal of several impurities by vacuum distillation at 115° C., distillation at 190° C. gave 13.7 g of 2-biphenyl-3-yl-5-methylpyridine as a viscous light yellow liquid, which was further purified on a silica gel column with ethyl acetate/hexane to give 12.8 g (87.1% yield) of 2-biphenyl-3-yl-5-methylpyridine as a white solid.

Quelle