Acetic Acid → 4-Fluoro-2-iodophenol

HRID 46302Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 46302
[I:1]N1C(=O)CCC1=O.[F:9][C:10]1[CH:15]=[CH:14][C:13]([OH:16])=[CH:12][CH:11]=1.C(O)(=O)C.S(=O)(=O)(O)O>O>[F:9][C:10]1[CH:15]=[CH:14][C:13]([OH:16])=[C:12]([I:1])[CH:11]=1

Komponenten

6

Edukt 4

HCID 176Acetic AcidHCID 1118Sulfuric AcidHCID 97324-FluorophenolHCID 120273N-Iodosuccinimide

Produkt 1

HCID 101714174-Fluoro-2-iodophenolAusbeute 40 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 962WaterLösungsmittel

Versuchsvorschrift

N-Iodosuccinimide (10 g, 45.0 mmol) and 4-fluoro-phenol (5.00 g, 40.0 mmol) were suspended in acetic acid (39 ml, 649.0 mmol) and stirred for 5 minutes before addition of concentrated sulphuric acid (0.79 ml, 13.4 mmol). The reaction mixture was stirred for 18 hours at room temperature before diluting with water (100 ml). The aqueous layer was extracted with dichloromethane (2×30 ml). The combined organic extracts were washed with sodium thiosulphate solution (20% aqueous, wt:v), water, dried over sodium sulfate, filtered and concentrated in vacuo. The crude residue was purified by column chromatography (silica gel) eluting with toluene to afford the title compound as an off white solid, 4.5 g, 40% yield.

Aufarbeitung

  1. extractionThe aqueous layer was extracted with dichloromethane (2×30 ml)
  2. washThe combined organic extracts were washed with sodium thiosulphate solution (20% aqueous, wt:v), water
  3. dry with materialdried over sodium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo
  6. customThe crude residue was purified by column chromatography (silica gel)
  7. washeluting with toluene

Quellen und Nachweise

ORD-Eintrag
ord-a229e06029324e1fb38eae258f9d1935
Quelldatensatz
uspto-grants-2013_09
Patentnummer
US08541588B2

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