Dimethyl Sulfoxide → m-Trifluoromethylphenylacetonitrile

HRID 638225

Reaktionsgleichung

Reaktionsgleichung von HRID 638225
[F:1][C:2]([F:12])([F:11])[C:3]1[CH:4]=[C:5]([CH:8]=[CH:9][CH:10]=1)[CH2:6]Cl.[C-:13]#[N:14].[Na+].CS(C)=O>O>[F:1][C:2]([F:12])([F:11])[C:3]1[CH:4]=[C:5]([CH2:6][C:13]#[N:14])[CH:8]=[CH:9][CH:10]=1

Komponenten

5

Edukt 3

HCID 679Dimethyl SulfoxideHCID 8929Sodium CyanideHCID 697163-(Trifluoromethyl)benzyl chloride

Produkt 1

HCID 75360m-TrifluoromethylphenylacetonitrileAusbeute 107,1 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 962WaterLösungsmittel

Versuchsvorschrift

A mixture of 12.0 g (61.5 mmole) m-trifluoromethylbenzyl chloride, 9.56 g (195 mmole) sodium cyanide and 60 ml dimethylsulfoxide was heated at 50° to 80° C. for four hours and poured into water. The aqueous mixture was extracted with methylene chloride, the extracts dried over sodium sulfate and the solvent evaporated in vacuo to give 12.2 g of yellow oil which was used in the next step. 1H-NMR(CDCl3)ppm(delta): 3.80 (s, 2H), 7.60 (s, 4H).

Aufarbeitung

  1. temperaturewas heated at 50° to 80° C. for four hours
  2. extractionThe aqueous mixture was extracted with methylene chloride
  3. dry with materialthe extracts dried over sodium sulfate
  4. customthe solvent evaporated in vacuo

Quellen und Nachweise

ORD-Eintrag
ord-d46f14b90c1e453ea64887a24298fe1f
Quelldatensatz
uspto-grants-1985_12
Patentnummer
US04560690

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