Ethanol → Ethyl 2-fluoro-4-iodobenzoate

HRID 635557

Reaktionsgleichung

Reaktionsgleichung von HRID 635557
[F:1][C:2]1[CH:10]=[C:9]([I:11])[CH:8]=[CH:7][C:3]=1[C:4]([OH:6])=[O:5].[CH2:12](O)[CH3:13].S(=O)(=O)(O)O>>[F:1][C:2]1[CH:10]=[C:9]([I:11])[CH:8]=[CH:7][C:3]=1[C:4]([O:6][CH2:12][CH3:13])=[O:5]

Komponenten

4

Edukt 3

HCID 702EthanolHCID 1118Sulfuric AcidHCID 27745162-Fluoro-4-iodobenzoic acid2×

Produkt 1

HCID 18761561Ethyl 2-fluoro-4-iodobenzoate

Reaktionsbedingungen

Temperatur
90 °C

Versuchsvorschrift

To a solution of 2.5 g (27.0 mmol) of 2-fluoro-4-iodobenzoic acid (Compound B) in 11 mL (8.6 g, 187.5 mmol) of ethanol was added 0.3 mL of c. sulfuric acid. The reaction mixture was heated to reflux in an oil bath (90° C.) for 1.75 hours, fitted with a short path distillation apparatus, distilled and then allowed to cool to ambient temperature. The reaction mixture was extracted and partitioned between pentane and water and the layers were separated. The aqueous phase was washed with pentane and the organic phases were combined. The combined organic phase was washed sequentially with sat. NaHCO3 (aq.) solution, water and brine, dried over MgSO4, filtered and concentrated in vacuo to a purple oil. Purification by flash chromatography (silica, 10% ethyl acetate in hexane) gave the title compound as an orange oil. PMR (CDCl3): δ 1.39 (3 H, t, J=7.1 Hz), 4.39 (2 H, q, J=7.1 Hz), 7.52-7.67 (3 H, m).

Aufarbeitung

  1. temperatureThe reaction mixture was heated
  2. customfitted with a short path distillation apparatus
  3. distillationdistilled
  4. temperatureto cool to ambient temperature
  5. extractionThe reaction mixture was extracted
  6. custompartitioned between pentane and water
  7. customthe layers were separated
  8. washThe aqueous phase was washed with pentane
  9. washThe combined organic phase was washed sequentially with sat. NaHCO3 (aq.) solution, water and brine
  10. dry with materialdried over MgSO4
  11. filtrationfiltered
  12. concentrationconcentrated in vacuo to a purple oil
  13. customPurification by flash chromatography (silica, 10% ethyl acetate in hexane)

Quellen und Nachweise

ORD-Eintrag
ord-2589b79ccfaa44fe8fcf983660f1bf49
Quelldatensatz
uspto-grants-2001_02
Patentnummer
US06187950B1

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