Ethyl Acetate → 2-(4,5-Difluoro-2-nitro-phenylamino)-5-trifluoromethyl-benzonitrile

HRID 131335

Reaktionsgleichung

Reaktionsgleichung von HRID 131335
F[C:2]1[CH:9]=[CH:8][C:7]([C:10]([F:13])([F:12])[F:11])=[CH:6][C:3]=1[C:4]#[N:5].[F:14][C:15]1[C:20]([F:21])=[CH:19][C:18]([NH2:22])=[C:17]([N+:23]([O-:25])=[O:24])[CH:16]=1.O.[OH-].[Li+].C(OCC)(=O)C>CS(C)=O>[F:14][C:15]1[C:20]([F:21])=[CH:19][C:18]([NH:22][C:2]2[CH:9]=[CH:8][C:7]([C:10]([F:13])([F:12])[F:11])=[CH:6][C:3]=2[C:4]#[N:5])=[C:17]([N+:23]([O-:25])=[O:24])[CH:16]=1

Komponenten

6

Edukt 4

HCID 8857Ethyl AcetateHCID 1571514,5-Difluoro-2-nitroanilineHCID 168937Lithium hydroxide, monohydrateHCID 5210162-Fluoro-5-(trifluoromethyl)benzonitrile

Produkt 1

HCID 586259642-(4,5-Difluoro-2-nitro-phenylamino)-5-trifluoromethyl-benzonitrileAusbeute 50,5 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 679Dimethyl SulfoxideLösungsmittel

Versuchsvorschrift

Heat a solution of 2-fluoro-5-trifluoromethyl-benzonitrile (1.0 g, 5.74 mmol) with 4,5-difluoro-2-nitro-phenylamine (1.09 g, 5.74 mmol) and lithium hydroxide monohydrate (0.48 g, 11.49 mmol) in DMSO (12 ml) to 55° C. for 16 hours. Cool the reaction to ambient temperature and then add approximately 150 ml of ice water and stir the mixture for one hour. Extract with three 200 ml portions of dichloromethane. Combine organic layers, dry over sodium sulfate and evaporate solvent. Purify the residue via flash chromatography eluting with a linear gradient starting with 100% hexanes and going to 70% hexanes: 30% ethyl acetate to obtain 0.995 g (2.90 mmol, 50% yield) of the title compound as a yellow amorphous solid: Mass Spectrum (m/e): 344 (M+1).

Aufarbeitung

  1. temperatureCool
  2. customthe reaction to ambient temperature
  3. extractionExtract with three 200 ml portions of dichloromethane
  4. dry with materialCombine organic layers, dry over sodium sulfate
  5. customevaporate solvent
  6. customPurify the residue via flash chromatography
  7. washeluting with a linear gradient

Quellen und Nachweise

ORD-Eintrag
ord-9f2ac96a8a4a4b6999fcc549bb9bedd3
Quelldatensatz
uspto-grants-2008_06
Patentnummer
US07384934B2

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