2-Iodo-4-(trifluoromethyl)aniline → 4-Amino-3-cyanobenzotrifluoride

HRID 17030

Reaktionsgleichung

Reaktionsgleichung von HRID 17030
[NH2:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]([F:11])([F:10])[F:9])=[CH:4][C:3]=1I.[Cu](C#N)[C:14]#[N:15].C(OCC)(=O)C.CCCCCC>CN(C=O)C.[Hg]>[NH2:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]([F:11])([F:10])[F:9])=[CH:4][C:3]=1[C:14]#[N:15]

Komponenten

6

Edukt 3

HCID 27833222-Iodo-4-(trifluoromethyl)anilineHCID 21226206Ethyl acetate hexaneHCID 178418260HCID 178418260, Verbindung

Produkt 1

HCID 126273614-Amino-3-cyanobenzotrifluorideAusbeute 105 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 23931MercuryKatalysatorHCID 6228DimethylformamideLösungsmittel

Reaktionsbedingungen

Temperatur
100 °C

Versuchsvorschrift

In a 2-liter flask equipped with a septum inlet, magnetic stirring bar, and condenser leading to a mercury bubbler was placed 100 g (0.348 mol) of 4-amino-3-iodobenzotrifluoride in 1 liter DMF. To this reaction flask with stirring was added 37.4 g (0.416 mol) of copper cyanide and the contents were heated to 100° C. under nitrogen for fourteen hours. Afterwards, TLC analysis revealed minor starting material (20/80) ethyl acetate/hexane. The contents were cooled to 40° C. and filtered through a pad of Celite. The solids were washed with ether and the filtrate transferred to a separatory funnel and washed with about 5% aqueous ammonium hydroxide. The aqueous layer was back-extracted with ether and the organics were combined and washed with brine, dried over magnesium sulfate, filtered and concentrated to yield a black oil. The oil was chromatographed on a Biotage 75L cartridge with ethyl acetate/hexane to obtain 68 g 2-amino-5-(trifluoromethyl)benzonitrile as a black solid.

Aufarbeitung

  1. customIn a 2-liter flask equipped with a septum inlet, magnetic stirring bar, and condenser
  2. temperatureThe contents were cooled to 40° C.
  3. filtrationfiltered through a pad of Celite
  4. washThe solids were washed with ether
  5. customthe filtrate transferred to a separatory funnel
  6. washwashed with about 5% aqueous ammonium hydroxide
  7. extractionThe aqueous layer was back-extracted with ether
  8. washwashed with brine
  9. dry with materialdried over magnesium sulfate
  10. filtrationfiltered
  11. concentrationconcentrated
  12. customto yield a black oil
  13. customThe oil was chromatographed on a Biotage 75L cartridge with ethyl acetate/hexane

Quellen und Nachweise

ORD-Eintrag
ord-f2cdae7306054d90a7be368476e099d5
Quelldatensatz
uspto-grants-2010_06
Patentnummer
US07737295B2

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