反应 #2320125

反应方程式

2-Bromo-5-methylpyridine

3-bromophenylboronic acid

triphenylphosphine

potassium carbonate

→

2-(3-bromophenyl)-5-methylpyridine

收率 68.1%

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 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 then 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
    workup.DISTILLATIONAfter the excess 2-bromo-5-methylpyridine was distilled off in vacuo at 110° C.
11. 11
    workup.DISTILLATIONthe 2-(3-bromophenyl)-5-methylpyridine was distilled at 200° C.
12. 12
    其他to give 30.1 g (68.1% yield) of a slightly orange liquid, which
13. 13
    其他was used for the next step without further purification

实验过程

2-Bromo-5-methylpyridine (46.1 g, 267 mmol), 3-bromophenylboronic acid (35.8 g, 178 mmol), palladium(II) acetate (1.00 g, 4.4 mmol), triphenylphosphine (4.67 g, 17.8 mmol), and potassium carbonate (67.8 g, 491 mmol) were mixed with 370 mL of ethylene glycol dimethyl ether and 245 mL of water in a 1000 mL round bottom flask equipped with a temperature probe, reflux condenser, and a magnetic stir bar. The solution was heated at reflux under nitrogen for 16 hr. The cooled reaction mixture was then 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 excess 2-bromo-5-methylpyridine was distilled off in vacuo at 110° C., the 2-(3-bromophenyl)-5-methylpyridine was distilled at 200° C. to give 30.1 g (68.1% yield) of a slightly orange liquid, which was used for the next step without further purification.

来源