Reaktion #806236

Reaktionsgleichung

10-(biphenyl-4-yl)-7-bromo-12,12-dimethyl-10,12-dihydroindeno[2,1-b]carbazole

bis(biphenyl-4-yl)-[4-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)phenyl]amine

potassium carbonate

→

10-(biphenyl-4-yl)-7-[4-bis(biphenyl-4-yl)amino-phenyl]-12,12-dimethyl-10,12-dihydroindeno[2,1-b]carbazole

Ausbeute 63.8%

Lösungsmittel

toluene ethanol

Reaktionsbedingungen

Aufarbeitung

1. 1
   TemperaturThe mixture was heated
2. 2
   TemperaturAfter the mixture was cooled to a room temperature
3. 3
   Sonstigea precipitated crude product
4. 4
   Filtrationwas collected by filtration
5. 5
   workup.ADDITION1,2-Dichlorobenzene (1.7 L) was added to the crude product
6. 6
   workup.DISSOLUTIONthe crude product was dissolved
7. 7
   Temperaturwhile being heated
8. 8
   Sonstigeafter removing insoluble matter
9. 9
   Filtrationby filtration
10. 10
    Temperatura filtrate was cooled to a room temperature
11. 11
    FiltrationA precipitated solid was collected by filtration
12. 12
    Sonstigepurified by recrystallization

Vorschrift

10-(biphenyl-4-yl)-7-bromo-12,12-dimethyl-10,12-dihydroindeno[2,1-b]carbazole synthesized in Example 6 (13.0 g), bis(biphenyl-4-yl)-[4-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)phenyl]amine (15.9 g) a toluene/ethanol (4/1, v/v) mixed solvent (250 ml), and a 2M potassium carbonate aqueous solution (51 ml) were added to a nitrogen-substituted reaction vessel and aerated with nitrogen gas for 30 min under ultrasonic irradiation. The mixture was heated after adding tetrakis(triphenylphosphine)palladium (2.1 g), and stirred at 73° C. for 10 hours. After the mixture was cooled to a room temperature, a precipitated crude product was collected by filtration. 1,2-Dichlorobenzene (1.7 L) was added to the crude product, and the crude product was dissolved while being heated, and after removing insoluble matter by filtration, a filtrate was cooled to a room temperature. A precipitated solid was collected by filtration and purified by recrystallization using 1,2-dichlorobenzene (1.7 L) to obtain a white powder of 10-(biphenyl-4-yl)-7-[4-bis(biphenyl-4-yl)amino-phenyl]-12,12-dimethyl-10,12-dihydroindeno[2,1-b]carbazole (13.4 g; yield 63.8%).

Quelle