Реакция #657267

Уравнение реакции

3-Methylphenyl borate

2-chloro-3,7-dimethylquinoline

potassium carbonate

→

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

Растворители

THF

H2O

Условия реакции

Обработка

1. 1
   ДругоеAfter completion of the reaction
2. 2
   Другоеthe THF and the toluene were removed
3. 3
   ЭкстракцияThe reaction mixture was extracted with dichloromethane and water
4. 4
   workup.DISTILLATIONThe extract was distilled under reduced pressure
5. 5
   Другоеpurified by silica gel column chromatography
6. 6
   workup.DISTILLATIONThe eluate was distilled under reduced pressure
7. 7
   Другоеrecrystallized from dichloromethane and petroleum ether
8. 8
   Другоеto obtain a precipitate
9. 9
   ФильтрацияThe precipitate was filtered

Методика

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.

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