Trimethylsilylacetylene → ((4-Chloro-2-fluorophenyl)ethynyl)trimethylsilane

HRID 59332

Reaktionsgleichung

Reaktionsgleichung von HRID 59332
[Cl:1][C:2]1[CH:7]=[CH:6][C:5](I)=[C:4]([F:9])[CH:3]=1.[C:10]([Si:12]([CH3:15])([CH3:14])[CH3:13])#[CH:11]>CS(C)=O.[Cu](I)I.[Pd](Cl)Cl.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:11]#[C:10][Si:12]([CH3:15])([CH3:14])[CH3:13])=[C:4]([F:9])[CH:3]=1

Komponenten

6

Edukt 2

HCID 66111TrimethylsilylacetyleneHCID 27365624-Chloro-2-fluoro-1-iodobenzene

Produkt 1

HCID 90019293((4-Chloro-2-fluorophenyl)ethynyl)trimethylsilaneAusbeute 56,5 %

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 83717Copper iodideKatalysatorHCID 6102075Dichlorobis(triphenylphosphine)palladiumKatalysatorHCID 679Dimethyl SulfoxideLösungsmittel

Versuchsvorschrift

To a solution of 4-chloro-2-fluoro-1-iodobenzene (2.0 g, 7.8 mmol) in DMSO (10 mL) was added ethynyl(trimethyl)silane (1.14 g, 11.0 mmol), copper iodide (0.029 g, 0.15 mmol), bis(triphenylphosphine) palladium(II) chloride (0.218 g, 0.3 mmol) and TEA (1 mL). The reaction mass was stirred at RT for 4-5 h. The reaction mass quenched in water, passed through celite bed and extracted with ethyl acetate and concentrated to afford 1.0 g of desired product.

Aufarbeitung

  1. customThe reaction mass quenched in water
  2. extractionextracted with ethyl acetate
  3. concentrationconcentrated

Quellen und Nachweise

ORD-Eintrag
ord-649418e8072746319213417db71ea5ca
Quelldatensatz
uspto-grants-2016_09
Patentnummer
US09439890B2

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