반응 #577218

반응 방정식

sodium carbonate

4-methylphenyl-boronic acid

1-chloroisoquinoline

toluene

→

1-(4-methylphenyl)isoquinoline

수율 51.1%

용매

ethanol

반응 조건

후처리

1. 1
   workup.ADDITIONwas added
2. 2
   온도Thereafter, reflux
3. 3
   기타After completion of the reaction
4. 4
   온도the reaction product was cooled
5. 5
   추출extracted by addition of cold water and toluene
6. 6
   세척The organic layer washed with saline water
7. 7
   기타dried on magnesium sulfate
8. 8
   기타followed by removal of the solvent under a reduced pressure
9. 9
   기타to provide
10. 10
    기타dry solid The residue
11. 11
    기타was purified by silica gel column chromatography (eluent: chloroform/methanol=10/1)

실험 절차

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.

출처