Iodine → 5-Ethyl-2-iodophenol

HRID 1167307

Reaktionsgleichung

Reaktionsgleichung von HRID 1167307
[I:1]I.[CH2:3]([C:5]1[CH:6]=[C:7]([OH:11])[CH:8]=[CH:9][CH:10]=1)[CH3:4].C([O-])(=O)C.[Tl+]>C(Cl)Cl>[CH2:3]([C:5]1[CH:10]=[CH:9][C:8]([I:1])=[C:7]([OH:11])[CH:6]=1)[CH3:4]

Komponenten

5

Edukt 3

HCID 807IodineHCID 11247thallium(I) acetateHCID 121013-Ethylphenol

Produkt 1

HCID 229961995-Ethyl-2-iodophenolAusbeute 56,3 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel2×

Versuchsvorschrift

Iodine (6.35 g, 25 mmol) in methylene chloride (360 mL) was added dropwise over 3 h to a stirred suspension of 3-ethyl-phenol (3.05 g, 25 mmol) and thallium (I) acetate (7.90 g, 30 mmol) in methylene chloride (300 mL). The resulting mixture was stirred at room temperature for 24 h and filtered. The filtrate was concentrated in vacuo and the residue was purified by flash chromatography (Biotage system, KP-Sil™ 32-63 μm, 60 Å silica gel) eluting with 0-5% ethyl acetate in hexanes to afford 5-ethyl-2-iodophenol (3.49g, 56%).

Aufarbeitung

  1. filtrationfiltered
  2. concentrationThe filtrate was concentrated in vacuo
  3. customthe residue was purified by flash chromatography (Biotage system, KP-Sil™ 32-63 μm, 60 Å silica gel)
  4. washeluting with 0-5% ethyl acetate in hexanes

Quellen und Nachweise

ORD-Eintrag
ord-d91fbeefaf3d4c6fb2787296c9dca273
Quelldatensatz
uspto-grants-2003_09
Patentnummer
US06617346B1

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