Toluene → 9'-Phenyl-9-[4-(9-phenyl-9H-carbazol-3-yl)-phenyl]-9H,9'H-[3,3]bicarbazolyl

HRID 625202Notes

Reaction equation

HRID 625202 reaction equation
Br[C:2]1[CH:7]=[CH:6][C:5]([N:8]2[C:20]3[CH:19]=[CH:18][C:17]([C:21]4[CH:22]=[CH:23][C:24]5[N:25]([C:34]6[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=6)[C:26]6[C:31]([C:32]=5[CH:33]=4)=[CH:30][CH:29]=[CH:28][CH:27]=6)=[CH:16][C:15]=3[C:14]3[C:9]2=[CH:10][CH:11]=[CH:12][CH:13]=3)=[CH:4][CH:3]=1.[C:40]1([CH3:46])[CH:45]=[CH:44][CH:43]=[CH:42][CH:41]=1.C(=O)([O-])[O-].[K+].[K+]>C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.C(O)C>[C:34]1([N:25]2[C:24]3[CH:23]=[CH:22][C:21]([C:17]4[CH:18]=[CH:19][C:20]5[N:8]([C:5]6[CH:6]=[CH:7][C:2]([C:12]7[CH:11]=[CH:10][C:9]8[N:8]([C:5]9[CH:6]=[CH:7][CH:2]=[CH:3][CH:4]=9)[C:45]9[C:40]([C:46]=8[CH:13]=7)=[CH:41][CH:42]=[CH:43][CH:44]=9)=[CH:3][CH:4]=6)[C:9]6[C:14]([C:15]=5[CH:16]=4)=[CH:13][CH:12]=[CH:11][CH:10]=6)=[CH:33][C:32]=3[C:31]3[C:26]2=[CH:27][CH:28]=[CH:29][CH:30]=3)[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=1

Participants

6

Reactant 3

HCID 1140TolueneHCID 11430Potassium CarbonateHCID 680062349-(4-Bromophenyl)-9'-phenyl-9H,9'H-3,3'-bicarbazole

Product 1

HCID 681615769'-Phenyl-9-[4-(9-phenyl-9H-carbazol-3-yl)-phenyl]-9H,9'H-[3,3]bicarbazolylYield 48%

Reagents, catalysts & solvents 2

HCID 178418397HCID 178418397, compoundCatalystHCID 702EthanolSolvent

Conditions

Temperature
72 °C

Procedure

The resulting 9-(4-bromophenyl)-9′-phenyl-9H,9′H-[3,3′]bicarbazolyl (17.00 g), 9-phenyl-3-(4,4,5,5-tetramethyl-1,3,2-dioxabororan-2-yl)-9H-carbazole (12.25 g), toluene (160 ml), ethanol (40 ml), and a 2 M potassium carbonate aqueous solution (23 ml) were added to a nitrogen-substituted reaction vessel, and aerated with nitrogen gas for 30 minutes under ultrasonic waves. After adding tetrakis(triphenylphosphine)palladium (1.74 g), the mixture was heated, and stirred at 72° C. for 12.5 hours. The mixture was allowed to cool to room temperature, and extraction was performed by adding toluene (100 ml) and water (150 ml) thereto. The organic layer was dried over magnesium sulfate, and concentrated under reduced pressure to obtain a black crude product. The crude product was purified by column chromatography (carrier: silica gel; eluent: hexane/toluene) to obtain a pale yellowish white powder of 9′-phenyl-9-[4-(9-phenyl-9H-carbazol-3-yl)-phenyl]-9H,9′H-[3,3′]bicarbazolyl (10.44 g; yield 48%).

Workup

  1. temperaturethe mixture was heated
  2. temperatureto cool to room temperature
  3. extractionextraction
  4. additionby adding toluene (100 ml) and water (150 ml)
  5. dry with materialThe organic layer was dried over magnesium sulfate
  6. concentrationconcentrated under reduced pressure
  7. customto obtain a black crude product
  8. customThe crude product was purified by column chromatography (carrier: silica gel; eluent: hexane/toluene)

Sources & evidence

ORD record
ord-c1f8b059ddd649678fb4348b9b38ece0
Source dataset
uspto-grants-2016_04
Patent number
US09306175B2

Reaction notes

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