p-Fluoronitrobenzene → Nitro-4-(2,2,2-trifluoro-1-methyl-ethoxy)-benzene

HRID 2381159

Reaktionsgleichung

Reaktionsgleichung von HRID 2381159
F[C:2]1[CH:7]=[CH:6][C:5]([N+:8]([O-:10])=[O:9])=[CH:4][CH:3]=1.[F:11][C:12]([F:17])([F:16])[CH:13]([OH:15])[CH3:14].C([O-])([O-])=O.[Cs+].[Cs+]>C(#N)C>[N+:8]([C:5]1[CH:6]=[CH:7][C:2]([O:15][CH:13]([CH3:14])[C:12]([F:17])([F:16])[F:11])=[CH:3][CH:4]=1)([O-:10])=[O:9]

Komponenten

5

Edukt 3

HCID 9590p-FluoronitrobenzeneHCID 97741,1,1-Trifluoro-2-propanolHCID 10796Cesium carbonate

Produkt 1

HCID 66577895Nitro-4-(2,2,2-trifluoro-1-methyl-ethoxy)-benzeneAusbeute 95,4 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6342AcetonitrileLösungsmittel

Versuchsvorschrift

To a solution of 1-fluoro-4-nitro-benzene (4.24 g) and (rac)-1,1,1-trifluoro-propan-2-ol (4.563 g) in acetonitile (50 ml) under an argon atmosphere was added at RT Cs2CO3 (13.04 g) and the mixture was refluxed for 10 h. It was then acidified with diluted aqueous HCL and partitioned between ethyl acetate and water. The layers were separated, dried over Na2SO4 and the solvent was then evaporated off to give (rac)-1-nitro-4-(2,2,2-trifluoro-1-methyl-ethoxy)-benzene as brown oil (6.74 g) that was used without further purification.

Aufarbeitung

  1. temperaturethe mixture was refluxed for 10 h
  2. custompartitioned between ethyl acetate and water
  3. customThe layers were separated
  4. dry with materialdried over Na2SO4
  5. customthe solvent was then evaporated off

Quellen und Nachweise

ORD-Eintrag
ord-760b9606c1cc434d9867470cb9e9bc16
Quelldatensatz
uspto-grants-2012_09
Patentnummer
US08258158B2

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