Reaktion #657266

Reaktionsgleichung

3-Methylphenyl borate

2-chloro-3,6-dimethylquinoline

potassium carbonate

→

2-(3-methylphenyl)-3,6-dimethylquinoline

Lösungsmittel

THF

H2O

Reaktionsbedingungen

Aufarbeitung

1. 1
   SonstigeAfter completion of the reaction
2. 2
   Sonstigethe THF and the toluene were removed
3. 3
   ExtraktionThe reaction solution was extracted with dichloromethane and water
4. 4
   workup.DISTILLATIONdistilled under reduced pressure
5. 5
   SonstigeThe resulting residue was purified by silica gel column chromatography
6. 6
   workup.DISTILLATIONThe eluate was distilled under reduced pressure
7. 7
   SonstigeThe residue was recrystallized from dichloromethane and petroleum ether
8. 8
   Filtrationfiltered

Vorschrift

3-Methylphenyl borate (1.3 mmol), 2-chloro-3,6-dimethylquinoline (1 mmol), tetrakis(triphenylphosphine)palladium(O) (0.05 mmol) and potassium carbonate (3 mmol) were dissolved in THF (30 mL) and H2O (10 mL). The resulting solution was stirred in a bath at 100° C. for 24 hours. After completion of the reaction, the THF and the toluene were removed. The reaction solution was extracted with dichloromethane and water, and distilled under reduced pressure. The resulting residue was purified by silica gel column chromatography. The eluate was distilled under reduced pressure. The residue was recrystallized from dichloromethane and petroleum ether and filtered to yield 2-(3-methylphenyl)-3,6-dimethylquinoline as a solid.

Quelle