Réaction #2320126

Équation de réaction

2-(3-bromophenyl)-5-methylpyridine

phenylboronic acid

triphenylphosphine

potassium carbonate

→

2-biphenyl-3-yl-5-methylpyridine

Rendement 91.6%

Solvants

ethyl acetate

water

ethylene glycol dimethyl ether

Conditions de réaction

Traitement

1. 1
   Autreequipped with a temperature probe
2. 2
   Températurereflux condenser, and a magnetic stir bar
3. 3
   TempératureThe solution was then heated
4. 4
   Températureat reflux under nitrogen for 16 hr
5. 5
   AutreThe cooled reaction mixture
6. 6
   Autrewas placed in a separatory funnel
7. 7
   ExtractionThe organic layer was extracted twice with a saturated solution of sodium chloride
8. 8
   Séchagedried over magnesium sulfate
9. 9
   Autreevaporated to dryness
10. 10
    AutreAfter the removal of several impurities
11. 11
    workup.DISTILLATIONby vacuum distillation at 115° C.
12. 12
    workup.DISTILLATIONdistillation at 190° C.

Mode opératoire

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.

Source