Reaction #657267

Reaction equation

3-Methylphenyl borate

2-chloro-3,7-dimethylquinoline

potassium carbonate

→

2-(3-methylphenyl)-3,7-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 mixture was extracted with dichloromethane and water
4. 4
   workup.DISTILLATIONThe extract was distilled under reduced pressure
5. 5
   Otherpurified by silica gel column chromatography
6. 6
   workup.DISTILLATIONThe eluate was distilled under reduced pressure
7. 7
   Otherrecrystallized from dichloromethane and petroleum ether
8. 8
   Otherto obtain a precipitate
9. 9
   FiltrationThe precipitate was filtered

Procedure

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.

Source