Tris(1,1-dimethylethyl)phosphine → 11-(4-Carbazolylphenyl)indolo[2,3-a]carbazole

HRID 558042

Reaktionsgleichung

Reaktionsgleichung von HRID 558042
C(P(C(C)(C)C)C(C)(C)C)(C)(C)C.[CH:14]1[C:19]2[N:20]=[C:21]3[C:33]4[C:25]([C:26]5[C:31]([N:32]=4)=[CH:30][CH:29]=[CH:28][CH:27]=5)=[CH:24][CH:23]=[C:22]3[C:18]=2[CH:17]=[CH:16][CH:15]=1.[C:34]1([C:47]2[CH:52]=[CH:51][C:50](Br)=[CH:49][CH:48]=2)[C:46]2[NH:45][C:44]3[C:39](=[CH:40][CH:41]=[CH:42][CH:43]=3)[C:38]=2[CH:37]=[CH:36][CH:35]=1.CC(C)([O-])C.[Na+]>C1(C)C(C)=CC=CC=1.C([O-])(=O)C.[Pd+2].C([O-])(=O)C.O>[C:34]1([C:47]2[CH:52]=[CH:51][C:50]([N:20]3[C:21]4[C:22](=[CH:23][CH:24]=[C:25]5[C:26]6[CH:27]=[CH:28][CH:29]=[CH:30][C:31]=6[NH:32][C:33]5=4)[C:18]4[C:19]3=[CH:14][CH:15]=[CH:16][CH:17]=4)=[CH:49][CH:48]=2)[C:46]2[NH:45][C:44]3[C:39](=[CH:40][CH:41]=[CH:42][CH:43]=3)[C:38]=2[CH:37]=[CH:36][CH:35]=1

Komponenten

8

Edukt 4

HCID 83681Tris(1,1-dimethylethyl)phosphineHCID 21882147Indolo[2,3-a]carbazoleHCID 231439554-CarbazolylbromobenzeneHCID 23676156Sodium t-butoxide

Produkt 1

HCID 6693759811-(4-Carbazolylphenyl)indolo[2,3-a]carbazoleAusbeute 47 %

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 167845palladium(II) acetateKatalysatorHCID 962WaterLösungsmittelHCID 7237O-XyleneLösungsmittel2×

Reaktionsbedingungen

Temperatur
60 °C

Versuchsvorschrift

In a 100-ml three-necked flask were placed 0.21 g (0.94 mmole) of palladium(II) acetate, 20 ml of xylene, and 0.76 g (3.76 mmoles) of tri-tert-butylphosphine and the mixture was heated at 60° C. with stirring for 30 minutes. The resulting solution was sent into a solution that had been prepared by dissolving 4.61 g (0.0180 mole) of indolo[2,3-a]carbazole, 5.8 g (0.018 mole) of 4-carbazolylbromobenzene, and 7.7 g (0.080 mole) of sodium tert-butoxide in 180 ml of xylene and heated at 60° C. in a stream of nitrogen and the combined solution was heated up to 130° C. and kept at this temperature for 5 hours with stirring. The solution was cooled to room temperature, 200 ml of water was added, and the organic layer was separated and concentrated under reduced pressure to give a crude product. The crude product was purified by crystallization from dichloromethane and ethanol, the solvent was distilled off under reduced pressure, and 4.2 g (0.0084 mole, 47% yield) of 11-(4-carbazolylphenyl)indolo[2,3-a]carbazole was obtained.

Aufarbeitung

  1. customIn a 100-ml three-necked flask were placed
  2. customhad been prepared
  3. temperaturethe combined solution was heated up to 130° C.
  4. waitkept at this temperature for 5 hours
  5. stirringwith stirring
  6. temperatureThe solution was cooled to room temperature
  7. customthe organic layer was separated
  8. concentrationconcentrated under reduced pressure
  9. customto give a crude product
  10. customThe crude product was purified by crystallization from dichloromethane and ethanol
  11. distillationthe solvent was distilled off under reduced pressure

Quellen und Nachweise

ORD-Eintrag
ord-6858f3c062f24685a3d9f60c0b864aed
Quelldatensatz
uspto-grants-2011_11
Patentnummer
US08062769B2

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