反応 #66033

反応方程式

1-Bromo-4-methoxynaphthalene

4-(naphthalen-2-yl)phenylboronic acid

potassium carbonate

water

→

product

収率 68.6%

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

収率 68.6%

溶媒

toluene

tetrahydrofuran

反応条件

後処理

1. 1
   温度under reflux
2. 2
   その他After completion of the reaction
3. 3
   抽出extracted with ethyl acetate (300 mL) and water (1000 mL)
4. 4
   乾燥The organic layer was dried with magnesium sulfate
5. 5
   濃縮concentrated under reduced pressure
6. 6
   workup.DISSOLUTIONThe resulting solid was dissolved in hot toluene (400 mL)
7. 7
   ろ過filtered
8. 8
   その他The filtrate was recrystallized in methanol (800 mL)
9. 9
   ろ過The resultant solid was filtered
10. 10
    洗浄washed with hexane (300 mL)

実験手順

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%).

出典