Trimethylsilylacetylene → 1-[(Trimethylsilyl)ethynyl]-3-(trifluoromethyl)benzene

HRID 508827

Reaktionsgleichung

Reaktionsgleichung von HRID 508827
I[C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([C:8]([F:11])([F:10])[F:9])[CH:3]=1.[C:12]([Si:14]([CH3:17])([CH3:16])[CH3:15])#[CH:13]>C(OCC)(=O)C.[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>[CH3:15][Si:14]([CH3:17])([CH3:16])[C:12]#[C:13][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([C:8]([F:11])([F:10])[F:9])[CH:3]=1

Komponenten

6

Edukt 2

HCID 66111TrimethylsilylacetyleneHCID 67868Benzene, 1-iodo-3-(trifluoromethyl)-

Produkt 1

HCID 42818851-[(Trimethylsilyl)ethynyl]-3-(trifluoromethyl)benzeneAusbeute 57,3 %

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 83717Copper iodideKatalysatorHCID 6102075Dichlorobis(triphenylphosphine)palladiumKatalysatorHCID 8857Ethyl AcetateLösungsmittel

Reaktionsbedingungen

Temperatur
55 °C

Versuchsvorschrift

To a solution of 1-iodo-3-(trifluoromethyl)benzene (1.0 g, 3.6 mmol) in ethyl acetate (20 mL) was added ethynyl(trimethyl)silane (0.540 g, 5.5 mmol), copper iodide (0.042 g, 0.22 mmol), bis(triphenylphosphine) palladium(II) chloride (0.129 g, 0.18 mmol) and TEA (2.2 mL, 14.7 mmol). The reaction mass stirred at 50-60° C. for 24 h. The reaction mass was quenched in water, extracted with ethyl acetate and concentrated to afford 0.500 g of desired product. 1H NMR (300 MHz, DMSO d6): δ 0.26 (s, 9H), 7.44 (t, J=7.8 Hz, 1H), 7.55 (d, J=7.8 Hz, 1H), 7.62 (d, J=7.2 Hz, 1H), 7.72 (s, 1H).

Aufarbeitung

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

Quellen und Nachweise

ORD-Eintrag
ord-f2fa04a6e9be4f1489aada74d91affb4
Quelldatensatz
uspto-grants-2015_08
Patentnummer
US09096545B2

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