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Triethylamine → (4-Chlorophenylethynyl)trimethylsilane

HRID 1199594
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 1199594
[Cl:1][C:2]1[CH:7]=[CH:6][C:5](I)=[CH:4][CH:3]=1.C(N(CC)CC)C.[CH3:16][Si:17]([C:20]#[CH:21])([CH3:19])[CH3:18].[Cl-].[NH4+]>C(#N)C.[Cu](I)I.Cl[Pd](Cl)([P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)[P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1.CCCCCC>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:21]#[C:20][Si:17]([CH3:19])([CH3:18])[CH3:16])=[CH:4][CH:3]=1
KomponentenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

9

Edukt 4

HCID 8471TriethylamineHCID 125101-Chloro-4-iodobenzeneHCID 25517Ammonium ChlorideHCID 66111Trimethylsilylacetylene

Produkt 1

HCID 3337298(4-Chlorophenylethynyl)trimethylsilaneAusbeute 93,4 %

Reagenzien, Katalysatoren, Lösungsmittel 4

HCID 83717
Copper iodide
Katalysator
HCID 178418476HCID 178418476, VerbindungKatalysator
HCID 6342AcetonitrileLösungsmittel
HCID 8058HexaneLösungsmittel

Versuchsvorschrift

To a solution of 4-chloroiodobenzene (4.77 g:0.02 mole) in dry acetonitrile (30 ml) and triethylamine (2.02 g:0.02 mole) under nitrogen, was added copper iodide (0.2 g:1.05 mole), bis (triphenylphosphine)palladium dichloride (0.2 g=0.285 mmole) and trimethylsilylethyne (2.156 g:0.022 mole). The mixture was stirred for three hours during which time there was an exotherm at 20° C. and a darkening of the reacton mixture. The mixture was poured into saturated ammonium chloride solution (100 ml) and was extracted with ether (×3). The extracts were combined, washed with dilute hydrochloric acid and dried over magnesium sulfate and then filtered through charcoal. Removal of solvent in vacuo gave a brown oil which was titurated with hexane and filtered to remove by-products. The filtrate was evaporated to give yellow crystals (3.90 g).

Aufarbeitung

  1. customat 20° C.
  2. extractionwas extracted with ether (×3)
  3. washwashed with dilute hydrochloric acid
  4. dry with materialdried over magnesium sulfate
  5. filtrationfiltered through charcoal
  6. customRemoval of solvent in vacuo
  7. customgave a brown oil which
  8. filtrationfiltered
  9. customto remove by-products
  10. customThe filtrate was evaporated

Quellen und Nachweise

ORD-Eintrag
ord-ea74fe9d39b449a4ac066e630643b61a
Quelldatensatz
uspto-grants-1990_02
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US04902332

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