Reaction #66032

Reaction equation

1-Bromo-4-methoxynaphthalene

4-(naphthalen-1-yl)phenylboronic acid

potassium carbonate

water

→

product

Yield 52.6%

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

Yield 52.6%

Solvents

toluene

toluene

tetrahydrofuran

Conditions

Workup

1. 1
   Temperatureunder reflux
2. 2
   OtherAfter completion of the reaction
3. 3
   Extractionextracted with ethyl acetate (300 mL) and water (1000 mL)
4. 4
   DryingThe organic layer was dried with magnesium sulfate
5. 5
   Concentrationconcentrated under reduced pressure
6. 6
   Otherto obtain a solid
7. 7
   Filtrationfiltered
8. 8
   OtherThe filtrate was recrystallized in methanol (800 mL)
9. 9
   FiltrationThe resultant solid was filtered
10. 10
    Washwashed with hexane (300 mL)

Procedure

1-Bromo-4-methoxynaphthalene (25 g, 0.105 mol), 4-(naphthalen-1-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 to obtain a solid. The solid was dissolved in hot toluene (400 mL) and then filtered. The filtrate was recrystallized in methanol (800 mL). The resultant solid was filtered and washed with hexane (300 mL) to obtain a product (20 g, 0.055 mol, 52.6%).

Source