2-Chloro-1-iodo-4-nitrobenzene → 2-Chloro-4-nitrobenzotrifluoride

HRID 1383657

Reaktionsgleichung

Reaktionsgleichung von HRID 1383657
[Cl:1][C:2]1[CH:3]=[C:4]([N+:9]([O-:11])=[O:10])[CH:5]=[CH:6][C:7]=1I.C[Si](C)(C)[C:14]([F:17])([F:16])[F:15].[F-].[K+]>CN(C)C=O.C(OCC)C.[Cu]I>[Cl:1][C:2]1[CH:3]=[C:4]([N+:9]([O-:11])=[O:10])[CH:5]=[CH:6][C:7]=1[C:14]([F:17])([F:16])[F:15]

Komponenten

7

Edukt 3

HCID 966402-Chloro-1-iodo-4-nitrobenzeneHCID 522689Potassium FluorideHCID 552549(Trifluoromethyl)trimethylsilane

Produkt 1

HCID 27789852-Chloro-4-nitrobenzotrifluoride

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)KatalysatorHCID 3283Diethyl EtherLösungsmittelHCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

A solution of 3-chloro-4-iodo-nitrobenzene (2.26 g), trimethyl(trifluoromethyl)silane (5.68 g), copper(I) iodide (2.28 g), and potassium fluoride (0.56 g) in N,N-dimethylformamide (8 mL) is heated in a sealed tube to 80° C. for 40 hours. The solution is then cooled, diluted with diethyl ether, filtered through diatomaceous earth, and the filtrate is washed successively with water, saturated aqueous sodium chloride, and then dried over anhydrous sodium sulfate. The solvent is removed under reduced pressure and the residue is chromatographed over silica gel (1% diethyl ether in hexanes followed by 10% ethyl acetate in hexanes is used as the eluant) to provided the desired product as a colorless oil.

Aufarbeitung

  1. temperatureThe solution is then cooled
  2. filtrationfiltered through diatomaceous earth
  3. washthe filtrate is washed successively with water, saturated aqueous sodium chloride
  4. dry with materialdried over anhydrous sodium sulfate
  5. customThe solvent is removed under reduced pressure
  6. customthe residue is chromatographed over silica gel (1% diethyl ether in hexanes

Quellen und Nachweise

ORD-Eintrag
ord-f11ee05d8cc9414481331892730e349e
Quelldatensatz
uspto-grants-2001_07
Patentnummer
US06255349B1

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