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Tris(1,1-dimethylethyl)phosphine → 9,10-bis(4-fluorophenyl)-2-[N-phenyl-N-(9-phenyl-9H-carbazol-3-yl)amino]anthracene

HRID 2243463
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 2243463
Br[C:2]1[CH:15]=[CH:14][C:13]2[C:4](=[C:5]([C:23]3[CH:28]=[CH:27][C:26]([F:29])=[CH:25][CH:24]=3)[C:6]3[C:11]([C:12]=2[C:16]2[CH:21]=[CH:20][C:19]([F:22])=[CH:18][CH:17]=2)=[CH:10][CH:9]=[CH:8][CH:7]=3)[CH:3]=1.[C:30]1([NH:36][C:37]2[CH:38]=[CH:39][C:40]3[N:41]([C:50]4[CH:55]=[CH:54][CH:53]=[CH:52][CH:51]=4)[C:42]4[C:47]([C:48]=3[CH:49]=2)=[CH:46][CH:45]=[CH:44][CH:43]=4)[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=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>[F:29][C:26]1[CH:27]=[CH:28][C:23]([C:5]2[C:6]3[C:11]([C:12]([C:16]4[CH:17]=[CH:18][C:19]([F:22])=[CH:20][CH:21]=4)=[C:13]4[C:4]=2[CH:3]=[C:2]([N:36]([C:30]2[CH:31]=[CH:32][CH:33]=[CH:34][CH:35]=2)[C:37]2[CH:38]=[CH:39][C:40]5[N:41]([C:50]6[CH:55]=[CH:54][CH:53]=[CH:52][CH:51]=6)[C:42]6[C:47]([C:48]=5[CH:49]=2)=[CH:46][CH:45]=[CH:44][CH:43]=6)[CH:15]=[CH:14]4)=[CH:10][CH:9]=[CH:8][CH:7]=3)=[CH:24][CH:25]=1
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Komponenten

7

Edukt 4

HCID 83681Tris(1,1-dimethylethyl)phosphineHCID 23676156Sodium t-butoxideHCID 592111052-Bromo-9,10-bis(4-fluorophenyl)anthraceneHCID 59815954N,9-Diphenyl-9H-carbazol-3-amine

Produkt 1

HCID 592110179,10-bis(4-fluorophenyl)-2-[N-phenyl-N-(9-phenyl-9H-carbazol-3-yl)amino]anthraceneAusbeute 63,6 %

Reagenzien, Katalysatoren, Lösungsmittel 2

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

Reaktionsbedingungen

Temperatur
80 °C

Versuchsvorschrift

2.0 g (4.5 mmol) of 2-bromo-9,10-bis(4-fluorophenyl)anthracene, 1.7 g (4.9 mmol) of N,9-diphenyl-9H-carbazol-3-amine (PCA), 0.13 g (0.23 mmol) of bis(dibenzylideneacetone)palladium(0), and 1.1 g (11 mmol) of sodium tert-butoxide were put into a 100 mL three-neck flask, and the atmosphere of the flask was substituted with nitrogen. Thereafter, 30 mL of toluene and 0.45 g (0.23 mmol) of tri(tert-butyl)phosphine (10% hexane solution) were added to the mixture, and this reaction mixture was stirred for 6 hours at 80° C. After the reaction was completed, the reaction solution was washed with water, and the aqueous layer was extracted with ethyl acetate. The extracted solution was combined with the organic layer, and then dried with magnesium sulfate. After drying, this mixture was subjected to suction filtration, and the filtrate was concentrated. The obtained residue was purified by silica gel column chromatography (eluent: toluene), and then concentrated. The obtained solid was recrystallized with a mixed solvent of chloroform and hexane, giving 2.0 g of 9,10-bis(4-fluorophenyl)-2-[N-phenyl-N-(9-phenyl-9H-carbazol-3-yl)amino]anthracene (abbreviation: 2PCAFPA) as yellow powder in 62% yield. By nuclear magnetic resonance measurement (NMR), this compound was determined to be 9,10-bis(4-fluorophenyl)-2-[N-phenyl-N-(9-phenyl-9H-carbazol-3-yl)amino]anthracene (abbreviation: 2PCAFPA).

Aufarbeitung

  1. washthe reaction solution was washed with water
  2. extractionthe aqueous layer was extracted with ethyl acetate
  3. dry with materialdried with magnesium sulfate
  4. customAfter drying
  5. filtrationthis mixture was subjected to suction filtration
  6. concentrationthe filtrate was concentrated
  7. customThe obtained residue was purified by silica gel column chromatography (eluent: toluene)
  8. concentrationconcentrated
  9. customThe obtained solid was recrystallized with a mixed solvent of chloroform and hexane

Quellen und Nachweise

ORD-Eintrag
ord-d2fbe411599b4f43a942077b399cfd38
Quelldatensatz
uspto-grants-2010_03
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US07674914B2

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