Réaction #657266

Équation de réaction

3-Methylphenyl borate

2-chloro-3,6-dimethylquinoline

potassium carbonate

→

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

Solvants

THF

H2O

Conditions de réaction

Traitement

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

Mode opératoire

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.

Source