Реакция #68709

Уравнение реакции

3-Methylphenyl borate

2-chloro-6-methoxyquinoline

potassium carbonate

→

2-(3-methylphenyl)-6-methoxyquinoline

Растворители

THF

H2O

Условия реакции

Обработка

1. 1
   ДругоеAfter completion of the reaction
2. 2
   Другоеthe solvents were removed
3. 3
   ЭкстракцияThe reaction mixture was extracted with dichloromethane and water
4. 4
   workup.DISTILLATIONdistilled under reduced pressure
5. 5
   ДругоеThe resulting residue was purified by silica gel column chromatography
6. 6
   workup.DISTILLATIONThe eluate was distilled under reduced pressure
7. 7
   ДругоеThe residue was recrystallized from dichloromethane and petroleum ether
8. 8
   Фильтрацияfiltered

Методика

3-Methylphenyl borate (1.3 mmol), 2-chloro-6-methoxyquinoline (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 solvents were removed. The reaction mixture 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)-6-methoxyquinoline as a solid.

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