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

HRID 604216Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 604216
Br[C:2]1[CH:3]=[C:4]([CH2:12][OH:13])[CH:5]=[C:6]([C:8]([F:11])([F:10])[F:9])[CH:7]=1.[CH3:14][N:15](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>[OH:13][CH2:12][C:4]1[CH:3]=[C:2]([CH:7]=[C:6]([C:8]([F:11])([F:10])[F:9])[CH:5]=1)[C:14]#[N:15]

Komponenten

5

Edukt 2

HCID 6228DimethylformamideHCID 29919767[3-Bromo-5-(trifluoromethyl)phenyl]methanol

Produkt 1

HCID 117012213-(Hydroxymethyl)-5-(trifluoromethyl)benzonitrile

Reagenzien, Katalysatoren, Lösungsmittel 2

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

Reaktionsbedingungen

Temperatur
120 °C

Versuchsvorschrift

(3-Bromo-5-trifluoromethyl-phenyl)-methanol (33.9 g) is dissolved in N,N-dimethylformamide (400 mL) and thereto are added zinc(II) cyanide (16.39 g) and tetrakis(triphenylphosphine)palladium (7.68 g) and the mixture is heated under nitrogen atmosphere at 120° C. for 2 hours. The reaction solution is allowed to cool to room temperature, and filtered through Celite™, and the filtrate is concentrated under reduced pressure. Thereto is added water and the mixture is extracted with ethyl acetate. The organic layer is washed with a saturated brine, dried over sodium sulfate, and concentrated under reduced pressure. The resulting residue is purified by silica gel column chromatography (hexane:ethyl acetate=2:1) to give 3-hydroxymethyl-5-trifluoromethyl-benzonitrile (23.4 g). NMR (CDCl3): 2.09 (1H, t), 4.85 (2H, d), 7.83 (1H, s), 7.87 (2H, s)

Aufarbeitung

  1. temperatureto cool to room temperature
  2. filtrationfiltered through Celite™
  3. concentrationthe filtrate is concentrated under reduced pressure
  4. additionThereto is added water
  5. extractionthe mixture is extracted with ethyl acetate
  6. washThe organic layer is washed with a saturated brine
  7. dry with materialdried over sodium sulfate
  8. concentrationconcentrated under reduced pressure
  9. customThe resulting residue is purified by silica gel column chromatography (hexane:ethyl acetate=2:1)

Quellen und Nachweise

ORD-Eintrag
ord-8d85a83425b548c39e8d155bfb910745
Quelldatensatz
uspto-grants-2011_03
Patentnummer
US07906517B2

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