反应 #577218

反应方程式

sodium carbonate

4-methylphenyl-boronic acid

1-chloroisoquinoline

toluene

→

1-(4-methylphenyl)isoquinoline

收率 51.1%

溶剂

ethanol

反应条件

后处理

1. 1
   workup.ADDITIONwas added
2. 2
   温度Thereafter, reflux
3. 3
   其他After completion of the reaction
4. 4
   温度the reaction product was cooled
5. 5
   萃取extracted by addition of cold water and toluene
6. 6
   洗涤The organic layer washed with saline water
7. 7
   其他dried on magnesium sulfate
8. 8
   其他followed by removal of the solvent under a reduced pressure
9. 9
   其他to provide
10. 10
    其他dry solid The residue
11. 11
    其他was purified by silica gel column chromatography (eluent: chloroform/methanol=10/1)

实验过程

In a 200 ml-three-necked flask, 3.40 g (25.0 mmole) of 4-methylphenyl-boronic acid (made by Aldrich Co.), 4.09 g (25.0 mmole) of 1-chloroisoquinoline, 25 ml of toluene, 12.5 ml of ethanol and 25 mol of 2M-sodium carbonate aqueous solution were placed and stirred at room temperature under nitrogen stream, and 0.98 g (0.85 mmole) of tetrakis(triphenylphosphine)-palladium (0) was added thereto. Thereafter, reflux under stirring was performed for 8 hours under nitrogen stream. After completion of the reaction, the reaction product was cooled and extracted by addition of cold water and toluene. The organic layer washed with saline water and dried on magnesium sulfate, followed by removal of the solvent under a reduced pressure to provide dry solid The residue was purified by silica gel column chromatography (eluent: chloroform/methanol=10/1) to obtain 2.80 g (yield=51.1%) of 1-(4-methylphenyl)isoquinoline.

来源