反应 #2320126

反应方程式

2-(3-bromophenyl)-5-methylpyridine

phenylboronic acid

triphenylphosphine

potassium carbonate

→

2-biphenyl-3-yl-5-methylpyridine

收率 91.6%

溶剂

ethyl acetate

water

ethylene glycol dimethyl ether

反应条件

后处理

1. 1
   其他equipped with a temperature probe
2. 2
   温度reflux condenser, and a magnetic stir bar
3. 3
   温度The solution was then heated
4. 4
   温度at reflux under nitrogen for 16 hr
5. 5
   其他The cooled reaction mixture
6. 6
   其他was placed in a separatory funnel
7. 7
   萃取The organic layer was extracted twice with a saturated solution of sodium chloride
8. 8
   干燥dried over magnesium sulfate
9. 9
   其他evaporated to dryness
10. 10
    其他After the removal of several impurities
11. 11
    workup.DISTILLATIONby vacuum distillation at 115° C.
12. 12
    workup.DISTILLATIONdistillation at 190° C.

实验过程

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.

来源