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Bromobenzene → 9,9''-Diphenyl-9H,9'H,9''H-3,3':6',3''-tercarbazole

HRID 1050709
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Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 1050709
[C:1]1([N:7]2[C:19]3[CH:18]=[CH:17][C:16](B4OC(C)(C)C(C)(C)O4)=[CH:15][C:14]=3[C:13]3[C:8]2=[CH:9][CH:10]=[CH:11][CH:12]=3)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.Br[C:30]1[CH:31]=[CH:32][C:33]2[NH:34][C:35]3[C:40]([C:41]=2[CH:42]=1)=[CH:39][C:38](Br)=[CH:37][CH:36]=3.C([O-])([O-])=O.[K+].[K+].Br[C:51]1[CH:56]=[CH:55][CH:54]=[CH:53][CH:52]=1>C1(C)C=CC=CC=1.O.CCO.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:51]1([N:34]2[C:35]3[CH:36]=[CH:37][C:38]([C:11]4[CH:10]=[CH:9][C:8]5[NH:7][C:19]6[C:14]([C:13]=5[CH:12]=4)=[CH:15][C:16]([C:4]4[CH:3]=[CH:2][C:1]5[N:7]([C:19]7[CH:14]=[CH:15][CH:16]=[CH:17][CH:18]=7)[C:8]7[C:13]([C:6]=5[CH:5]=4)=[CH:12][CH:11]=[CH:10][CH:9]=7)=[CH:17][CH:18]=6)=[CH:39][C:40]=3[C:41]3[C:33]2=[CH:32][CH:31]=[CH:30][CH:42]=3)[CH:56]=[CH:55][CH:54]=[CH:53][CH:52]=1
KomponentenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

9

Edukt 4

HCID 7961BromobenzeneHCID 11430Potassium CarbonateHCID 2748743,6-DibromocarbazoleHCID 574156959-Phenyl-3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)carbazole

Produkt 1

HCID 593067259,9''-Diphenyl-9H,9'H,9''H-3,3':6',3''-tercarbazoleAusbeute 65,4 %

Reagenzien, Katalysatoren, Lösungsmittel 4

HCID 178418397HCID 178418397, VerbindungKatalysatorHCID 702EthanolLösungsmittelHCID 962WaterLösungsmittelHCID 1140TolueneLösungsmittel

Versuchsvorschrift

A solution of 9-phenyl-3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)carbazole (7.1 g, 19.2 mmol), 3,6-dibromo-9H-carbazole (2.6 g, 8.0 mmol), K2CO3 (11.0 g, 79.7 mmol) in toluene (120 mL), water (40 mL) and EtOH (40 mL) was bubbled for 30 minutes with nitrogen. Then, Pd(PPh3)4 (0.9 g, 0.8 mmol) was added. The mixture was bubbled with nitrogen for 15 minutes and refluxed for 10 hours, after which bromobenzene (0.9 mL, 8.6 mmol) was added. The resultant mixture was refluxed for 6 hours. After cooling, the reaction mixture was extracted with CH2Cl2 and dried with MgSO4. The solvent was removed in vacuo and the residue was purified by flash chromatography using 40-60% CH2Cl2/hexane to afford 3,6-bis(9-phenylcarbazol-3-yl)carbazole (3.4 g, 65% yield) as a white solid.

Aufarbeitung

  1. customThe mixture was bubbled with nitrogen for 15 minutes
  2. temperaturerefluxed for 10 hours
  3. temperatureAfter cooling
  4. extractionthe reaction mixture was extracted with CH2Cl2
  5. dry with materialdried with MgSO4
  6. customThe solvent was removed in vacuo
  7. customthe residue was purified by flash chromatography

Quellen und Nachweise

ORD-Eintrag
ord-7f3a8502306949178ead9adfc0d8248e
Quelldatensatz
uspto-grants-2016_07
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US09386657B2

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