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

HRID 59334

Reaktionsgleichung

Reaktionsgleichung von HRID 59334
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-db091dd852e94dac8377a99e56e3cd33
Quelldatensatz
uspto-grants-2016_09
Patentnummer
US09439890B2

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