Acetic Acid → 2-Fluoro-4-iodobenzoic acid

HRID 431692

Reaktionsgleichung

Reaktionsgleichung von HRID 431692
[Cr](O[Cr]([O-])(=O)=O)([O-])(=O)=O.[Na+].[Na+].[F:12][C:13]1[CH:18]=[C:17]([I:19])[CH:16]=[CH:15]C=1C.S(=O)(=O)(O)O.[C:26]([OH:29])(=[O:28])[CH3:27]>>[F:12][C:13]1[CH:18]=[C:17]([I:19])[CH:16]=[CH:15][C:27]=1[C:26]([OH:29])=[O:28]

Komponenten

5

Edukt 4

HCID 176Acetic AcidHCID 1118Sulfuric Acid2×HCID 25408Sodium DichromateHCID 1234922-Fluoro-4-iodotoluene

Produkt 1

HCID 27745162-Fluoro-4-iodobenzoic acid

Reaktionsbedingungen

Temperatur
90 °C

Versuchsvorschrift

A round bottom (RB) flask containing a solution of 8.0 g (27.0 8 mmol) of sodium dichromate in 44 mL of glacial acetic acid was placed in an external water bath (21° C.) and left exposed to air. To the resultant orange slurry was added 3.2 g (13.6 mmol) of 2-fluoro-4-iodotoluene followed by the dropwise addition of 22 mL of c. sulfuric acid via syringe (caution: if added too quickly there is a tendency for the mixture to erupt). After the addition of approximately 8 mL of sulfuric acid, a green solid precipitated and the water bath temperature had risen (25° C.). The green reaction mixture was heated in an oil bath (90° C.) for one hour, allowed to cool to ambient temperature, diluted with 1N NaOH solution (aq.) and ethyl acetate (500 mL) and then quenched with sat. NaHCO3 (aq.) solution. The organic phase was separated and washed with water and brine, dried over MgSO4, filtered and concentrated in vacuo to an orange oil. Residual acetic acid was removed by further extraction between ethyl acetate and sat. NaHCO3 (aq.) solution and washing of the organic phase with water and brine. The organic phase was dried over MgSO4, filtered and concentrated in vacuo to give the title compound as an orange solid.

Aufarbeitung

  1. customwas placed in an external water bath
  2. wait(21° C.) and left
  3. additionfollowed by the dropwise addition of 22 mL of c
  4. customa green solid precipitated
  5. custom(25° C.)
  6. temperatureto cool to ambient temperature
  7. additiondiluted with 1N NaOH solution (aq.) and ethyl acetate (500 mL)
  8. customquenched with sat. NaHCO3 (aq.) solution
  9. customThe organic phase was separated
  10. washwashed with water and brine
  11. dry with materialdried over MgSO4
  12. filtrationfiltered
  13. concentrationconcentrated in vacuo to an orange oil
  14. customResidual acetic acid was removed by further extraction between ethyl acetate and sat. NaHCO3 (aq.) solution
  15. washwashing of the organic phase with water and brine
  16. dry with materialThe organic phase was dried over MgSO4
  17. filtrationfiltered
  18. concentrationconcentrated in vacuo

Quellen und Nachweise

ORD-Eintrag
ord-1886ec609745486d9bbe5e57c9f18649
Quelldatensatz
uspto-grants-2003_12
Patentnummer
US06660755B2

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