Réaction #577218

Équation de réaction

sodium carbonate

4-methylphenyl-boronic acid

1-chloroisoquinoline

toluene

→

1-(4-methylphenyl)isoquinoline

Rendement 51.1%

Solvants

ethanol

Conditions de réaction

Traitement

1. 1
   workup.ADDITIONwas added
2. 2
   TempératureThereafter, reflux
3. 3
   AutreAfter completion of the reaction
4. 4
   Températurethe reaction product was cooled
5. 5
   Extractionextracted by addition of cold water and toluene
6. 6
   LavageThe organic layer washed with saline water
7. 7
   Autredried on magnesium sulfate
8. 8
   Autrefollowed by removal of the solvent under a reduced pressure
9. 9
   Autreto provide
10. 10
    Autredry solid The residue
11. 11
    Autrewas purified by silica gel column chromatography (eluent: chloroform/methanol=10/1)

Mode opératoire

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.

Source