Reaktion #806232

Reaktionsgleichung

7-Bromo-12,12-dimethyl-10-phenyl-10,12-dihydro-indeno[2,1-b]carbazole

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

potassium carbonate

→

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

Ausbeute 143.2%

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 (140 ml) 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
    Einengena filtrate was concentrated under reduced pressure
11. 11
    SonstigePurification
12. 12
    Sonstigeby recrystallization

Vorschrift

7-Bromo-12,12-dimethyl-10-phenyl-10,12-dihydro-indeno[2,1-b]carbazole synthesized in Example 1 (3.0 g), bis(biphenyl-4-yl)-[4-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)phenyl]amine (4.3 g), a toluene/ethanol (4/1, v/v) mixed solvent (50 ml), and a 2M potassium carbonate aqueous solution (10 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 (0.4 g), and stirred at 73° C. for 8 hours. After the mixture was cooled to a room temperature, a precipitated crude product was collected by filtration. 1,2-dichlorobenzene (140 ml) 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 concentrated under reduced pressure. Purification by recrystallization using 1,2-dichlorobenzene (100 ml) was performed to obtain a white powder of 7-[4-{bis(biphenyl-4-yl)amino}-phenyl]-12,12-dimethyl-10-phenyl-10,12-dihydroindeno[2,1-b]carbazole (3.7 g; yield 71.6%).

Quelle