反応 #1552052

反応方程式

3-methylphenyl boronic acid

2-chloro-6-fluoroquinoline

potassium carbonate

toluene

→

2-(3-methylphenyl)-6-fluoroquinoline

収率 80.1%

溶媒

H2O

tetrahydrofuran

THF

反応条件

後処理

1. 1
   その他are removed
2. 2
   抽出The reaction mixture is extracted with dichloromethane and water
3. 3
   workup.DISTILLATIONbeing distilled under reduced pressure
4. 4
   ろ過The resulting residence is filtered by silica gel column
5. 5
   workup.DISTILLATIONdistilled under reduced pressure again
6. 6
   その他Next, by re-crystallizing
7. 7
   ろ過filtering

実験手順

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.

出典