2,2,2-Trifluoroethanol → 2-Fluoro-4-(2,2,2-trifluoroethoxy)-5-chloronitrobenzene

HRID 654480Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 654480
[OH-].[K+].[CH2:3]([OH:8])[C:4]([F:7])([F:6])[F:5].[F:9][C:10]1[CH:15]=[C:14](F)[C:13]([Cl:17])=[CH:12][C:11]=1[N+:18]([O-:20])=[O:19]>CS(C)=O>[F:9][C:10]1[CH:15]=[C:14]([O:8][CH2:3][C:4]([F:7])([F:6])[F:5])[C:13]([Cl:17])=[CH:12][C:11]=1[N+:18]([O-:20])=[O:19]

Komponenten

5

Edukt 3

HCID 64092,2,2-TrifluoroethanolHCID 14797Potassium HydroxideHCID 738671-Chloro-2,4-difluoro-5-nitrobenzene

Produkt 1

HCID 198876532-Fluoro-4-(2,2,2-trifluoroethoxy)-5-chloronitrobenzene

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 679Dimethyl SulfoxideLösungsmittel2×

Versuchsvorschrift

22.5 g of 88% potassium hydroxide are suspended in 120 ml of dimethyl sulfoxide. With stirring, 40 g of trifluoroethanol are added dropwise to this suspension. Then, also with stirring, the resultant solution is added dropwise at room temperature to a solution of 96.8 g of 2,4-difluoro-5-chloronitrobenzene in 150 ml of dimethyl sulfoxide. When the addition is complete, the reaction mixture is stirred for a further 2 hours at room temperature. The reaction mixture is then concentrated, the crude product is dissolved in methylene chloride, and the resultant solution is washed with water and dried. Finally, the solvent is distilled off. Purification is effected by chromatography through a column of silica gel with a 10:1 mixture of hexane and ether as eluant. The solvent is distilled off, affording the title compound of the formula ##STR10## in the form of yellow crystals; m.p.: 54°-55° C.

Aufarbeitung

  1. stirringThen, also with stirring
  2. additionWhen the addition
  3. stirringthe reaction mixture is stirred for a further 2 hours at room temperature
  4. concentrationThe reaction mixture is then concentrated
  5. dissolutionthe crude product is dissolved in methylene chloride
  6. washthe resultant solution is washed with water
  7. customdried
  8. distillationFinally, the solvent is distilled off
  9. customPurification
  10. additionis effected by chromatography through a column of silica gel with a 10:1 mixture of hexane and ether as eluant
  11. distillationThe solvent is distilled off

Quellen und Nachweise

ORD-Eintrag
ord-30de927fa5ff45019fd563ab1c6cd524
Quelldatensatz
uspto-grants-1992_07
Patentnummer
US05132325

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