Ammonia → 1-Methoxy-4-(pentafluoroethyl)benzene

HRID 1028443Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1028443
I[C:2]1[CH:7]=[CH:6][C:5]([O:8][CH3:9])=[CH:4][CH:3]=1.[F:10][C:11]([Si](C)(C)C)([F:16])[C:12]([F:15])([F:14])[F:13].[F-].[K+].N>[Cu](I)I.CN(C)C=O>[CH3:9][O:8][C:5]1[CH:6]=[CH:7][C:2]([C:11]([F:16])([F:10])[C:12]([F:15])([F:14])[F:13])=[CH:3][CH:4]=1

Komponenten

7

Edukt 4

HCID 222AmmoniaHCID 696764-IodoanisoleHCID 522689Potassium FluorideHCID 2760820(Pentafluoroethyl)trimethylsilane2×

Produkt 1

HCID 128719661-Methoxy-4-(pentafluoroethyl)benzene

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 83717Copper iodideKatalysatorHCID 6228DimethylformamideLösungsmittel

Reaktionsbedingungen

Temperatur
80 °C

Versuchsvorschrift

A mixture of 2.00 g 4-iodo-anisol, 2.00 g pentafluoroethyl-trimethylsilane, 0.60 g potassium fluoride, 2.43 g copper iodide and 15 ml N,N-dimethylformamide is stirred overnight at 80° C. Then the mixture is stirred for a further 36 h at 80° C., while a further 2.00 g pentafluoroethyl-trimethylsilane are added after 4 h, 12 h and 24 h. After cooling to ambient temperature 2 M aqueous ammonia solution is added and the mixture is filtered. The filtrate is extracted with ethyl acetate, and the combined organic extracts are dried (Na2SO4) and evaporated down. The residue is chromatographed on silica gel with petroleum ether/ethyl acetate (9:1) as eluant.

Aufarbeitung

  1. additionare added after 4 h, 12 h and 24 h
  2. additionis added
  3. filtrationthe mixture is filtered
  4. extractionThe filtrate is extracted with ethyl acetate
  5. dry with materialthe combined organic extracts are dried (Na2SO4)
  6. customevaporated down
  7. customThe residue is chromatographed on silica gel with petroleum ether/ethyl acetate (9:1) as eluant

Quellen und Nachweise

ORD-Eintrag
ord-7449dac406db4be992cd1fdd0fc97c99
Quelldatensatz
uspto-grants-2014_05
Patentnummer
US08735579B2

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