Hexane → HCID 87183733, Verbindung

HRID 551334Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 551334
[Br-].[F:2][C:3]([F:8])([F:7])[C:4]([Zn+])=[CH2:5].[Cl:9][C:10]1[CH:15]=[CH:14][C:13](I)=[CH:12][C:11]=1[C:17]([F:20])([F:19])[F:18].CCCCCC>O1CCCC1.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>[Cl:9][C:10]1[CH:15]=[CH:14][C:13]([C:4]([C:3]([F:8])([F:7])[F:2])=[CH2:5])=[CH:12][C:11]=1[C:17]([F:20])([F:19])[F:18]

Komponenten

6

Edukt 3

HCID 8058HexaneHCID 431453922-Chloro-5-iodobenzotrifluorideHCID 178477747HCID 178477747, Verbindung

Produkt 1

HCID 87183733HCID 87183733, Verbindung

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 178418476HCID 178418476, VerbindungKatalysatorHCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

To 1M solution of 1-(trifluoromethyl)ethenyl zinc bromide in tetrahydrofuran (see J. Org. Chem. 1991, 56, 7336 for preparation) (53 mL) under nitrogen atmosphere was added 2-chloro-5-iodobenzotrifluoride (7.1 g), followed by the addition of dichlorobis(triphenylphosphine)palladium(II) (0.65 g). The mixture was stirred under reflux for 2.5 hours and then cooled to room temperature. To the resulting mixture was added hexane (100 mL) and filtered, and the filtrate was washed with water (50 mL) and brine, dried over anhydrous sodium sulfate and concentrated under reduced pressure to provide a residue. The residue was purified by column chromatography on silica gel eluted with hexane to afford the title compound as colorless oil (4.8 g).

Aufarbeitung

  1. temperatureunder reflux for 2.5 hours
  2. filtrationfiltered
  3. washthe filtrate was washed with water (50 mL) and brine
  4. dry with materialdried over anhydrous sodium sulfate
  5. concentrationconcentrated under reduced pressure
  6. customto provide a residue
  7. customThe residue was purified by column chromatography on silica gel
  8. washeluted with hexane

Quellen und Nachweise

ORD-Eintrag
ord-3ee0830583c148b9b67144e57051eb12
Quelldatensatz
uspto-grants-2011_05
Patentnummer
US07947715B2

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