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Tris(1,1-dimethylethyl)phosphine → 3-(Dibenzofuran-2-yl)-9-[4-(10-phenyl-9-anthryl)phenyl]-9H-carbazole

HRID 1747206
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Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 1747206
Br[C:2]1[CH:7]=[CH:6][C:5]([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:4][CH:3]=1.[CH:28]1[C:36]2[C:35]3[CH:37]=[CH:38][CH:39]=[CH:40][C:34]=3[O:33][C:32]=2[CH:31]=[CH:30][C:29]=1[C:41]1[CH:42]=[CH:43][C:44]2[NH:45][C:46]3[C:51]([C:52]=2[CH:53]=1)=[CH:50][CH:49]=[CH:48][CH:47]=3.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].CCCCCC.C1(C)C=CC=CC=1>[CH:28]1[C:36]2[C:35]3[CH:37]=[CH:38][CH:39]=[CH:40][C:34]=3[O:33][C:32]=2[CH:31]=[CH:30][C:29]=1[C:41]1[CH:42]=[CH:43][C:44]2[N:45]([C:2]3[CH:3]=[CH:4][C:5]([C:8]4[C:21]5[C:16]([C:15]([C:22]6[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=6)=[C:14]6[C:9]=4[CH:10]=[CH:11][CH:12]=[CH:13]6)=[CH:17][CH:18]=[CH:19][CH:20]=5)=[CH:6][CH:7]=3)[C:46]3[C:51]([C:52]=2[CH:53]=1)=[CH:50][CH:49]=[CH:48][CH:47]=3
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Komponenten

8

Edukt 4

HCID 83681Tris(1,1-dimethylethyl)phosphineHCID 221382759-(4-Bromophenyl)-10-phenylanthraceneHCID 23676156Sodium t-butoxideHCID 579976693-(Dibenzofuran-2-yl)-9H-carbazole

Produkt 1

HCID 866645023-(Dibenzofuran-2-yl)-9-[4-(10-phenyl-9-anthryl)phenyl]-9H-carbazoleAusbeute 81,4 %

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 6505921(1E,4E)-1,5-diphenylpenta-1,4-dien-3-one; palladiumKatalysatorHCID 1140TolueneLösungsmittelHCID 8058HexaneLösungsmittel

Versuchsvorschrift

Into a 200-mL three-neck flask were put 1.0 g (2.6 mmol) of 9-(4-bromophenyl)-10-phenylanthracene, 0.86 g (2.6 mmol) of 3-(dibenzofuran-2-yl)-9H-carbazole, and 0.50 g (5.2 mmol) of sodium tert-butoxide. The air in the flask was replaced with nitrogen, and then, to the mixture were added 50 mL of toluene and 0.20 mL of tri(tert-butyl)phosphine (a 10 wt % hexane solution). This mixture was degassed under reduced pressure while being stirred, and then 75 mg (0.13 mmol) of bis(dibenzylideneacetone)palladium(0) was added to this mixture. This mixture was stirred at 110° C. for 2 hours under a nitrogen stream. After the stirring, this mixture was subjected to suction filtration through Celite, alumina, and Florisil. The obtained filtrate was concentrated to give a light-yellow oily substance. This oily substance was recrystallized from toluene/hexane to give 1.4 g of light-yellow powder in 80% yield. The synthesis scheme of Step 4 is shown in (a-4).

Aufarbeitung

  1. customInto a 200-mL three-neck flask were put
  2. customThis mixture was degassed under reduced pressure
  3. stirringThis mixture was stirred at 110° C. for 2 hours under a nitrogen stream
  4. filtrationAfter the stirring, this mixture was subjected to suction filtration through Celite, alumina, and Florisil
  5. concentrationThe obtained filtrate was concentrated
  6. customto give a light-yellow oily substance
  7. customThis oily substance was recrystallized from toluene/hexane

Quellen und Nachweise

ORD-Eintrag
ord-b15e93f4dda84e0ebbc876958a79b2e7
Quelldatensatz
uspto-grants-2015_10
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US09150551B2

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