반응 #66033

반응 방정식

1-Bromo-4-methoxynaphthalene

4-(naphthalen-2-yl)phenylboronic acid

potassium carbonate

water

→

product

수율 68.6%

1-methoxy-4-{4-(naphthalen-2-yl)phenyl}naphthalene

수율 68.6%

용매

toluene

tetrahydrofuran

반응 조건

후처리

1. 1
   온도under reflux
2. 2
   기타After completion of the reaction
3. 3
   추출extracted with ethyl acetate (300 mL) and water (1000 mL)
4. 4
   건조The organic layer was dried with magnesium sulfate
5. 5
   농축concentrated under reduced pressure
6. 6
   workup.DISSOLUTIONThe resulting solid was dissolved in hot toluene (400 mL)
7. 7
   여과filtered
8. 8
   기타The filtrate was recrystallized in methanol (800 mL)
9. 9
   여과The resultant solid was filtered
10. 10
    세척washed with hexane (300 mL)

실험 절차

1-Bromo-4-methoxynaphthalene (25 g, 0.105 mol), 4-(naphthalen-2-yl)phenylboronic acid (30.4 g, 0.137 mol), potassium carbonate (21.9 g, 0.16 mol), tetrakis(triphenylphosphine)palladium(0) (2.4 g, 0.01 mol), water (25 mL), tetrahydrofuran (75 mL) and toluene (75 mL) were stirred in a 250 mL round-bottom flask for 12 hours under reflux. After completion of the reaction, the reaction mixture was cooled to room temperature and extracted with ethyl acetate (300 mL) and water (1000 mL). The organic layer was dried with magnesium sulfate and concentrated under reduced pressure. The resulting solid was dissolved in hot toluene (400 mL) and filtered. The filtrate was recrystallized in methanol (800 mL). The resultant solid was filtered and washed with hexane (300 mL) to obtain a product (26 g, 0.072 mol, 68.4%).

출처