Reaction #1552052

Reaction equation

3-methylphenyl boronic acid

2-chloro-6-fluoroquinoline

potassium carbonate

toluene

→

2-(3-methylphenyl)-6-fluoroquinoline

Yield 80.1%

Solvents

H2O

tetrahydrofuran

THF

Conditions

Workup

1. 1
   Otherare removed
2. 2
   ExtractionThe reaction mixture is extracted with dichloromethane and water
3. 3
   workup.DISTILLATIONbeing distilled under reduced pressure
4. 4
   FiltrationThe resulting residence is filtered by silica gel column
5. 5
   workup.DISTILLATIONdistilled under reduced pressure again
6. 6
   OtherNext, by re-crystallizing
7. 7
   Filtrationfiltering

Procedure

3-methylphenyl boronic acid (13 mmol), 2-chloro-6-fluoroquinoline (10 mmol), tetrakis(triphenylphosphine)palladium(0) (0.5 mmol) and potassium carbonate (15 g) are put in a two-neck round-bottom flask and dissolved in tetrahydrofuran (THF) (30 mL) and H2O (10 mL). Subsequently, the resulting solution is stirred in a bath under a temperature of about 100° C. for 24 hours. After completion of the reaction, THF and toluene are removed. The reaction mixture is extracted with dichloromethane and water, and then being distilled under reduced pressure. The resulting residence is filtered by silica gel column and distilled under reduced pressure again. Next, by re-crystallizing and filtering, 2-(3-methylphenyl)-6-fluoroquinoline (1.9 g) is yielded.

Source