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Trimethylsilylacetylene → Tris(4-((trimethylsilyl)ethynyl)phenyl)amine

HRID 1840694
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Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 1840694
Br[C:2]1[CH:7]=[CH:6][C:5]([N:8]([C:16]2[CH:21]=[CH:20][C:19](Br)=[CH:18][CH:17]=2)[C:9]2[CH:14]=[CH:13][C:12](Br)=[CH:11][CH:10]=2)=[CH:4][CH:3]=1.[CH3:23][Si:24]([C:27]#[CH:28])([CH3:26])[CH3:25]>[Cu](I)I.C(NC(C)C)(C)C>[CH3:23][Si:24]([C:27]#[C:28][C:2]1[CH:7]=[CH:6][C:5]([N:8]([C:16]2[CH:21]=[CH:20][C:19]([C:28]#[C:27][Si:24]([CH3:26])([CH3:25])[CH3:23])=[CH:18][CH:17]=2)[C:9]2[CH:14]=[CH:13][C:12]([C:28]#[C:27][Si:24]([CH3:26])([CH3:25])[CH3:23])=[CH:11][CH:10]=2)=[CH:4][CH:3]=1)([CH3:26])[CH3:25]
KomponentenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

5

Edukt 2

HCID 66111TrimethylsilylacetyleneHCID 258027Tris(4-bromophenyl)amine

Produkt 1

HCID 23443707Tris(4-((trimethylsilyl)ethynyl)phenyl)amineAusbeute 81 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 83717Copper iodideKatalysatorHCID 7912DiisopropylamineLösungsmittel

Versuchsvorschrift

Thereafter, to 200 ml of diisopropylamine were added 15.54 g (0.032 mol of tri(4-bromophenyl)amine, 1.35 g (1.92 mmol) of bis[triphenylphosphin]palladium dichloride and 9.43 g (0.96 mmol) of copper iodide. After the reaction mixture was stirred for 2 h at room temperature, 9.43 g, (96 mmol) of trimethylsilyl acetylene was slowly added to the reaction mixture. The reaction mixture was refluxed for 8 h and cooled. Solvent was removed under the reduced pressure. The residue was extracted with benzene and the benzene layer was washed with distilled water. The washed benzene layer was concentrated to give 13.84 g (81%) of tri(4-trimethylsilylethynylphenyl)amine.

Aufarbeitung

  1. temperatureThe reaction mixture was refluxed for 8 h
  2. temperaturecooled
  3. customSolvent was removed under the reduced pressure
  4. extractionThe residue was extracted with benzene
  5. washthe benzene layer was washed with distilled water
  6. concentrationThe washed benzene layer was concentrated

Quellen und Nachweise

ORD-Eintrag
ord-c28251a72e284fd682b010ce47b24c90
Quelldatensatz
uspto-grants-2004_01
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US06682782B2

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