Réaction #68709

Équation de réaction

3-Methylphenyl borate

2-chloro-6-methoxyquinoline

potassium carbonate

→

2-(3-methylphenyl)-6-methoxyquinoline

Solvants

THF

H2O

Conditions de réaction

Traitement

1. 1
   AutreAfter completion of the reaction
2. 2
   Autrethe solvents were removed
3. 3
   ExtractionThe reaction mixture 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-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.

Source