Reaction #657266

Reaction equation

3-Methylphenyl borate

2-chloro-3,6-dimethylquinoline

potassium carbonate

→

2-(3-methylphenyl)-3,6-dimethylquinoline

Solvents

THF

H2O

Conditions

Workup

1. 1
   OtherAfter completion of the reaction
2. 2
   Otherthe THF and the toluene were removed
3. 3
   ExtractionThe reaction solution was extracted with dichloromethane and water
4. 4
   workup.DISTILLATIONdistilled under reduced pressure
5. 5
   OtherThe resulting residue was purified by silica gel column chromatography
6. 6
   workup.DISTILLATIONThe eluate was distilled under reduced pressure
7. 7
   OtherThe residue was recrystallized from dichloromethane and petroleum ether
8. 8
   Filtrationfiltered

Procedure

3-Methylphenyl borate (1.3 mmol), 2-chloro-3,6-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 solution 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)-3,6-dimethylquinoline as a solid.

Source