Dimethylformamide → 3-Amino-5-(trifluoromethyl)benzonitrile

HRID 517714Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 517714
Br[C:2]1[CH:3]=[C:4]([CH:6]=[C:7]([C:9]([F:12])([F:11])[F:10])[CH:8]=1)[NH2:5].[CH3:13][N:14](C)C=O>[C-]#N.[Zn+2].[C-]#N.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[NH2:5][C:4]1[CH:3]=[C:2]([CH:8]=[C:7]([C:9]([F:12])([F:11])[F:10])[CH:6]=1)[C:13]#[N:14]

Komponenten

5

Edukt 2

HCID 6228DimethylformamideHCID 27358803-Bromo-5-(trifluoromethyl)aniline

Produkt 1

HCID 225022643-Amino-5-(trifluoromethyl)benzonitrile

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 11186Zinc cyanide (Zn(CN)2)KatalysatorHCID 178418397HCID 178418397, VerbindungKatalysator

Reaktionsbedingungen

Temperatur
80 °C

Versuchsvorschrift

A solution of 3-bromo-5-(trifluoromethyl)aniline (3.24 g, 13.5 mmol) in N,N-dimethylformamide (50 mL) was degassed by bubbling argon through the solution for 30 minutes. To the reaction was added zinc cyanide (0.872 g, 7.42 mmol) and tetrakis(triphenylphosphine)palladium(0) (0.624 g, 0.54 mmol). The reaction was heated to 80° C. and stirred for 20 hours. The solvent was removed from the reaction under vacuum and the residue purified by silica chromatography (Biotage SP4, eluting 15% EtOAc in iso-hexane (4 column volumes) then a gradient from 15-30% (over 6 column volumes)) to yield the title compound as a colourless oil (2.20 g).

Aufarbeitung

  1. customby bubbling argon through the solution for 30 minutes
  2. customThe solvent was removed from the reaction under vacuum
  3. customthe residue purified by silica chromatography (Biotage SP4
  4. washeluting 15% EtOAc in iso-hexane (4 column volumes)

Quellen und Nachweise

ORD-Eintrag
ord-c74da81e91324318b91d60ec84ef4017
Quelldatensatz
uspto-grants-2015_08
Patentnummer
US09115132B2

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