2-Bromo-4-trifluoromethylaniline → 4-Amino-3-cyanobenzotrifluoride

HRID 131327

Reaktionsgleichung

Reaktionsgleichung von HRID 131327
[Cu][C:2]#[N:3].Br[C:5]1[CH:10]=[C:9]([C:11]([F:14])([F:13])[F:12])[CH:8]=[CH:7][C:6]=1[NH2:15]>CN1CCCC1=O.C(OCC)(=O)C>[NH2:15][C:6]1[CH:5]=[CH:10][C:9]([C:11]([F:12])([F:13])[F:14])=[CH:8][C:7]=1[C:2]#[N:3]

Komponenten

5

Edukt 2

HCID 938992-Bromo-4-trifluoromethylanilineHCID 178418546HCID 178418546, Verbindung

Produkt 1

HCID 126273614-Amino-3-cyanobenzotrifluorideAusbeute 47 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 8857Ethyl AcetateLösungsmittelHCID 13387N-methyl-2-pyrrolidoneLösungsmittel

Versuchsvorschrift

Heat a mixture of copper (I) cyanide (2.24 g, 25.00 mmol) and 2-bromo-4-trifluoromethyl-phenylamine (5.0 g, 20.83 mmol from Avocado) in 1-methyl-2-pyrrolidinone (20 ml) to 195° C. for four hours. Dilute the reaction mixture with 100 ml of ethyl acetate and wash the dark solution twice with 28% aqueous ammonium hydroxide, twice with saturated aqueous sodium chloride (brine) and twice with water. Collect the organic layer, dry over sodium sulfate and remove the solvent under reduced pressure. Purify the residue via flash chromatography eluting with a step gradient starting with hexanes and going to 70% hexanes with 30% ethyl acetate to obtain 1.821 g (9.78 mmol, 47% yield) the title compound as a green amorphous solid: Mass Spectrum (m/e): 187(M+1).

Aufarbeitung

  1. temperatureHeat
  2. washwash the dark solution twice with 28% aqueous ammonium hydroxide
  3. customCollect the organic layer
  4. dry with materialdry over sodium sulfate
  5. customremove the solvent under reduced pressure
  6. customPurify the residue via flash chromatography
  7. washeluting with a step gradient

Quellen und Nachweise

ORD-Eintrag
ord-4be442a3741e4283909eab11721f7e9a
Quelldatensatz
uspto-grants-2008_06
Patentnummer
US07384934B2

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