Water → 5-Fluoro-3-methylbenzofuran

HRID 226095

Reaktionsgleichung

Reaktionsgleichung von HRID 226095
[C:1]([C:4]1[CH:14]=[C:13]([F:15])[CH:12]=[CH:11][C:5]=1[O:6][CH2:7]C(O)=O)(=O)[CH3:2].C([O-])(=O)C.[Na+].O>C(OC(=O)C)(=O)C>[F:15][C:13]1[CH:12]=[CH:11][C:5]2[O:6][CH:7]=[C:1]([CH3:2])[C:4]=2[CH:14]=1

Komponenten

5

Edukt 3

HCID 962WaterHCID 517045Sodium AcetateHCID 116585522-(2-Acetyl-4-fluorophenoxy)acetic acid

Produkt 1

HCID 116798475-Fluoro-3-methylbenzofuranAusbeute 81 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 7918Acetic AnhydrideLösungsmittel

Reaktionsbedingungen

Temperatur
110 °C

Versuchsvorschrift

(2-Acetyl-4-fluoro-phenoxy)-acetic acid (1.87 gm, 8.8 mmol) is dissolved in acetic anhydride (60 mL) and treated with sodium acetate (10 gm, 0.12 mol). The resulting mixture is heated to 110° C. for 5 hr, then cooled to 0° C. H2O (100 mL) is added and the solution is stirred overnight at room temperature. The aqueous solution is then extracted into Et2O (2×75 mL). The combined organic extracts are washed with 3% aqueous KOH (2×75 mL), H2O (2×75 mL) and brine (1×75 mL), then dried over Na2SO4, filtered and concentrated. The crude product is purified by chromatography using hexane to give the title compound (1.07 gm, 81% yield).

Aufarbeitung

  1. temperaturecooled to 0° C
  2. extractionThe aqueous solution is then extracted into Et2O (2×75 mL)
  3. washThe combined organic extracts are washed with 3% aqueous KOH (2×75 mL), H2O (2×75 mL) and brine (1×75 mL)
  4. dry with materialdried over Na2SO4
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customThe crude product is purified by chromatography

Quellen und Nachweise

ORD-Eintrag
ord-f885c5b69ce64084a3526fa07ea4d8af
Quelldatensatz
uspto-grants-2009_07
Patentnummer
US07557103B2

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