Réaction #657267

Équation de réaction

3-Methylphenyl borate

2-chloro-3,7-dimethylquinoline

potassium carbonate

→

2-(3-methylphenyl)-3,7-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 mixture was extracted with dichloromethane and water
4. 4
   workup.DISTILLATIONThe extract was distilled under reduced pressure
5. 5
   Autrepurified by silica gel column chromatography
6. 6
   workup.DISTILLATIONThe eluate was distilled under reduced pressure
7. 7
   Autrerecrystallized from dichloromethane and petroleum ether
8. 8
   Autreto obtain a precipitate
9. 9
   FiltrationThe precipitate was filtered

Mode opératoire

3-Methylphenyl borate (1.3 mmol), 2-chloro-3,7-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 mixture was extracted with dichloromethane and water. The extract was distilled under reduced pressure and purified by silica gel column chromatography. The eluate was distilled under reduced pressure and recrystallized from dichloromethane and petroleum ether to obtain a precipitate. The precipitate was filtered to yield 2-(3-methylphenyl)-3,7-dimethylquinoline as a solid.

Source