Reaktion #806235

Reaktionsgleichung

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

9-phenyl-3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-9H-carbazole

potassium carbonate

→

10-(biphenyl-4-yl)-12,12-dimethyl-7-(9-phenyl-9H-carbazol-3-yl)-10,12-dihydroindeno[2,1-b]carbazole

Ausbeute 45.2%

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 (450 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 crystallization

Vorschrift

The resulting 10-(biphenyl-4-yl)-7-bromo-12,12-dimethyl-10,12-dihydroindeno[2,1-b]carbazole (16.5 g), 9-phenyl-3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-9H-carbazole (14.2 g), a toluene/ethanol (4/1, v/v) mixed solvent (250 ml), and a 2M potassium carbonate aqueous solution (48 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 (1.9 g), and stirred at 73° C. for 5 hours. After the mixture was cooled to a room temperature, a precipitated crude product was collected by filtration. 1,2-Dichlorobenzene (450 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 crystallization using 1,2-dichlorobenzene (150 ml) and n-hexane (300 ml) was performed to obtain a white powder of 10-(biphenyl-4-yl)-12,12-dimethyl-7-(9-phenyl-9H-carbazol-3-yl)-10,12-dihydroindeno[2,1-b]carbazole (9.8 g; yield 45.2%).

Quelle