Реакция #2320126

Уравнение реакции

2-(3-bromophenyl)-5-methylpyridine

phenylboronic acid

triphenylphosphine

potassium carbonate

→

2-biphenyl-3-yl-5-methylpyridine

Выход 91.6%

Растворители

ethyl acetate

water

ethylene glycol dimethyl ether

Условия реакции

Обработка

1. 1
   Другоеequipped with a temperature probe
2. 2
   Температураreflux condenser, and a magnetic stir bar
3. 3
   ТемператураThe solution was then heated
4. 4
   Температураat reflux under nitrogen for 16 hr
5. 5
   ДругоеThe cooled reaction mixture
6. 6
   Другоеwas placed in a separatory funnel
7. 7
   ЭкстракцияThe organic layer was extracted twice with a saturated solution of sodium chloride
8. 8
   Сушкаdried over magnesium sulfate
9. 9
   Другоеevaporated to dryness
10. 10
    ДругоеAfter the removal of several impurities
11. 11
    workup.DISTILLATIONby vacuum distillation at 115° C.
12. 12
    workup.DISTILLATIONdistillation at 190° C.

Методика

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.

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