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Carbazole → 9-[3-(10-phenyl-9-anthryl)phenyl]-9H-carbazole

HRID 1895852
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Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 1895852
Br[C:2]1[CH:3]=[C:4]([C:8]2[C:9]3[C:14]([C:15]([C:22]4[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=4)=[C:16]4[C:21]=2[CH:20]=[CH:19][CH:18]=[CH:17]4)=[CH:13][CH:12]=[CH:11][CH:10]=3)[CH:5]=[CH:6][CH:7]=1.[CH:28]1[C:40]2[NH:39][C:38]3[C:33](=[CH:34][CH:35]=[CH:36][CH:37]=3)[C:32]=2[CH:31]=[CH:30][CH:29]=1.CC(C)([O-])C.[Na+].C(P(C(C)(C)C)C(C)(C)C)(C)(C)C>C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.[Pd].C1(C)C=CC=CC=1>[C:14]1([C:15]2[C:22]3[C:27](=[CH:26][CH:25]=[CH:24][CH:23]=3)[C:8]([C:4]3[CH:3]=[C:2]([N:39]4[C:40]5[CH:28]=[CH:29][CH:30]=[CH:31][C:32]=5[C:33]5[C:38]4=[CH:37][CH:36]=[CH:35][CH:34]=5)[CH:7]=[CH:6][CH:5]=3)=[C:21]3[C:16]=2[CH:17]=[CH:18][CH:19]=[CH:20]3)[CH:9]=[CH:10][CH:11]=[CH:12][CH:13]=1
KomponentenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

7

Edukt 4

HCID 6854CarbazoleHCID 83681Tris(1,1-dimethylethyl)phosphineHCID 23676156Sodium t-butoxideHCID 593021329-(3-Bromophenyl)-10-phenylanthracene

Produkt 1

HCID 588760209-[3-(10-phenyl-9-anthryl)phenyl]-9H-carbazoleAusbeute 73,4 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 6505921
(1E,4E)-1,5-diphenylpenta-1,4-dien-3-one; palladium
Katalysator
HCID 1140TolueneLösungsmittel

Versuchsvorschrift

Into a 200 mL three-neck flask were put 1.3 g (3.3 mmol) of 9-(3-bromophenyl)-10-phenylanthracene (abbr.: mPA), 0.55 g (3.3 mmol) of 9H-carbazole, and 0.63 g (6.6 mmol) of sodium tert-butoxide. After the air in the flask was replaced with nitrogen, 40 mL of toluene and 0.40 mL of tri(tert-butyl)phosphine (10 wt % hexane solution) were added to this mixture. This mixture was stirred to be degassed while the pressure was reduced. After the degassing, 95 mg (0.17 mmol) of bis(dibenzylideneacetone)palladium(0) was added to this mixture. This mixture was stirred under a nitrogen stream at 110° C. for 8 hours. After the stirring, this mixture was subjected to suction filtration through Celite (Wako Pure Chemical Industries, Ltd., catalog No.: 531-16855), alumina, and Florisil (Wako Pure Chemical Industries, Ltd., catalog No.: 540-00135). The obtained filtrate was concentrated to give a light-yellow oily substance. The obtained oily substance was recrystallized from toluene/hexane to give 1.2 g of a light-yellow solid, which was the object of the synthesis, in a yield of 71%.

Aufarbeitung

  1. customInto a 200 mL three-neck flask were put
  2. additionwere added to this mixture
  3. customto be degassed while the pressure
  4. stirringThis mixture was stirred under a nitrogen stream at 110° C. for 8 hours
  5. filtrationAfter the stirring, this mixture was subjected to suction filtration through Celite (Wako Pure Chemical Industries, Ltd., catalog No.: 531-16855), alumina, and Florisil (Wako Pure Chemical Industries, Ltd., catalog No.: 540-00135)
  6. concentrationThe obtained filtrate was concentrated
  7. customto give a light-yellow oily substance
  8. customThe obtained oily substance was recrystallized from toluene/hexane

Quellen und Nachweise

ORD-Eintrag
ord-3690f7eea10c464ea38b7bd344d5d121
Quelldatensatz
uspto-grants-2013_08
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US08518492B2

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