Reacción #657267

Ecuación de reacción

3-Methylphenyl borate

2-chloro-3,7-dimethylquinoline

potassium carbonate

→

2-(3-methylphenyl)-3,7-dimethylquinoline

Disolventes

THF

H2O

Condiciones de reacción

Tratamiento posterior

1. 1
   OtroAfter completion of the reaction
2. 2
   Otrothe THF and the toluene were removed
3. 3
   ExtracciónThe reaction mixture was extracted with dichloromethane and water
4. 4
   workup.DISTILLATIONThe extract was distilled under reduced pressure
5. 5
   Otropurified by silica gel column chromatography
6. 6
   workup.DISTILLATIONThe eluate was distilled under reduced pressure
7. 7
   Otrorecrystallized from dichloromethane and petroleum ether
8. 8
   Otroto obtain a precipitate
9. 9
   FiltraciónThe precipitate was filtered

Procedimiento

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.

Fuente