反应 #2314296

反应方程式

dibromopyridine

boronic acid

4-Octylphenylboronic acid

sodium carbonate

→

solid

收率 95.0%

5-Bromo-2-(4-octylphenyl)pyridine

收率 95.0%

溶剂

toluene

反应条件

后处理

1. 1
   其他To a 1000 mL round bottom flask equipped with a stirbar
2. 2
   其他A reflux condenser was attached
3. 3
   其他The cooled reaction mixture
4. 4
   萃取was extracted with 1:1 hexane
5. 5
   洗涤ethyl acetate, and the combined organic layers were washed with brine
6. 6
   干燥dried over magnesium sulfate
7. 7
   其他the solvent was removed in vacuo
8. 8
   workup.DISSOLUTIONThe solid product was dissolved in dichloromethane
9. 9
   过滤filtered
10. 10
    其他removed a higher Rf side product, and 2.5% E/H

实验过程

To a 1000 mL round bottom flask equipped with a stirbar was added dibromopyridine 7C (22.506 g), boronic acid 7B (22.356 g), tetrakis(triphenylphosphine)palladium(0) (3.294 g), saturated sodium carbonate solution (238 mL), and toluene (190 mL). A reflux condenser was attached and the reaction was heated at 100° C. for 24 hours. The cooled reaction mixture was extracted with 1:1 hexane:ethyl acetate, and the combined organic layers were washed with brine and dried over magnesium sulfate and the solvent was removed in vacuo. The solid product was dissolved in dichloromethane, placed on silica gel, and silica gel filtered. The elution solvents were hexane, which removed a higher Rf side product, and 2.5% E/H, resulting in 31.251 g of solid. The product was recrystallized from acetonitrile to give 30.125 g of a white solid.

来源