Reaktion #577216

Reaktionsgleichung

sodium carbonate

phenylboronic acid

1-chloroisoquinoline

toluene

→

1-phenylisoquinoline

Ausbeute 43.0%

Lösungsmittel

ethanol

Reaktionsbedingungen

Aufarbeitung

1. 1
   workup.ADDITIONwas added
2. 2
   TemperaturThereafter, reflux
3. 3
   SonstigeAfter completion of the reaction
4. 4
   Temperaturthe reaction product was cooled
5. 5
   Extraktionextracted by addition of cold water and toluene
6. 6
   WaschenThe organic layer was washed with saline water
7. 7
   Sonstigedried on magnesium sulfate
8. 8
   Sonstigefollowed by removal of the solvent under a reduced pressure
9. 9
   Sonstigeto provide
10. 10
    Sonstigedry solid
11. 11
    SonstigeThe residue was purified by silica gel column chromatography (eluent: chloroform/methanol 10/1)

Vorschrift

In a 100 ml-three-necked flask, 3.04 g (24.9 mmole) of phenylboronic acid (made by Tokyo Kasei), 4.0 g of (25.0 mmole) of 1-chloroisoquinoline, 25 ml of toluene, 12.5 ml of ethanol and 25 ml 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 was 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 2.20 g (yield=43.0%) of 1-phenylisoquinoline. FIG. 7 shows a 1H-NMR spectrum of a solution of the compound in heavy chloroform.

Quelle