Reaktion #1552052

Reaktionsgleichung

3-methylphenyl boronic acid

2-chloro-6-fluoroquinoline

potassium carbonate

toluene

→

2-(3-methylphenyl)-6-fluoroquinoline

Ausbeute 80.1%

Lösungsmittel

H2O

tetrahydrofuran

THF

Reaktionsbedingungen

Aufarbeitung

1. 1
   Sonstigeare removed
2. 2
   ExtraktionThe 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
   SonstigeNext, by re-crystallizing
7. 7
   Filtrationfiltering

Vorschrift

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.

Quelle