تفاعل #66033

معادلة التفاعل

1-Bromo-4-methoxynaphthalene

4-(naphthalen-2-yl)phenylboronic acid

potassium carbonate

water

→

product

المردود 68.6%

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

المردود 68.6%

المذيبات

toluene

tetrahydrofuran

ظروف التفاعل

المعالجة

1. 1
   درجة الحرارةunder reflux
2. 2
   أخرىAfter completion of the reaction
3. 3
   استخلاصextracted with ethyl acetate (300 mL) and water (1000 mL)
4. 4
   تجفيفThe organic layer was dried with magnesium sulfate
5. 5
   تركيزconcentrated under reduced pressure
6. 6
   workup.DISSOLUTIONThe resulting solid was dissolved in hot toluene (400 mL)
7. 7
   ترشيحfiltered
8. 8
   أخرىThe filtrate was recrystallized in methanol (800 mL)
9. 9
   ترشيحThe resultant solid was filtered
10. 10
    غسيلwashed with hexane (300 mL)

الإجراء التجريبي

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%).

المصدر