Реакция #66033

Уравнение реакции

1-Bromo-4-methoxynaphthalene

4-(naphthalen-2-yl)phenylboronic acid

potassium carbonate

water

→

product

Выход 68.6%

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

Выход 68.6%

Растворители

toluene

tetrahydrofuran

Условия реакции

Обработка

1. 1
   Температураunder reflux
2. 2
   ДругоеAfter completion of the reaction
3. 3
   Экстракцияextracted with ethyl acetate (300 mL) and water (1000 mL)
4. 4
   СушкаThe organic layer was dried with magnesium sulfate
5. 5
   Концентрированиеconcentrated under reduced pressure
6. 6
   workup.DISSOLUTIONThe resulting solid was dissolved in hot toluene (400 mL)
7. 7
   Фильтрацияfiltered
8. 8
   ДругоеThe filtrate was recrystallized in methanol (800 mL)
9. 9
   ФильтрацияThe resultant solid was filtered
10. 10
    Промывкаwashed with hexane (300 mL)

Методика

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%).

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