Iodine → 2-Chloro-6-(hydroxymethyl)-4-iodo-3-pyridinol

HRID 1072976

Reaktionsgleichung

Reaktionsgleichung von HRID 1072976
[Cl:1][C:2]1[C:7]([OH:8])=[CH:6][CH:5]=[C:4]([CH2:9][OH:10])[N:3]=1.C([O-])(O)=O.[Na+].[I:16]I.OS([O-])(=O)=O.[Na+]>O>[Cl:1][C:2]1[C:7]([OH:8])=[C:6]([I:16])[CH:5]=[C:4]([CH2:9][OH:10])[N:3]=1

Komponenten

6

Edukt 4

HCID 807IodineHCID 516892Sodium BicarbonateHCID 516919Sodium BisulfateHCID 114237422-Chloro-6-(hydroxymethyl)-3-pyridinol

Produkt 1

HCID 106845682-Chloro-6-(hydroxymethyl)-4-iodo-3-pyridinolAusbeute 62 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 962WaterLösungsmittel

Versuchsvorschrift

C1 (11.6 g, 72.7 mmol) and NaHCO3 (18.3 g, 218 mmol) are added to 200 mL H2O. The mixture is stirred until homogeneous, the flask is placed in an ice bath, iodine (19.4 g, 76.3 mmol) is added, and the reaction is stirred over the weekend at rt. The pH of the mixture is adjusted to 3 with 2N NaHSO4, and the mixture is extracted with 4×50 mL EtOAc. The combined organic layer is dried over MgSO4, is filtered, and the filtrate is concentrated in vacuo to a yellow solid. The crude solid is washed with EtOAc to provide 2-chloro-6-(hydroxymethyl)-4-iodo-3-pyridinol (C2) as an off-white solid (62% yield), and the filtrate is concentrated to a small volume and is chromatographed over 250 g silica gel (230-400 mesh) eluting with 2.5:4.5:4:0.1 EtOAc/CH2Cl2/hexane/acetic acid to afford additional pure C2 (12% yield). MS (EI) for C6H5Cl/NO2, m/z: 285(M)+.

Aufarbeitung

  1. customis placed in an ice bath
  2. stirringthe reaction is stirred over the weekend at rt
  3. extractionthe mixture is extracted with 4×50 mL EtOAc
  4. dry with materialThe combined organic layer is dried over MgSO4
  5. filtrationis filtered
  6. concentrationthe filtrate is concentrated in vacuo to a yellow solid
  7. washThe crude solid is washed with EtOAc

Quellen und Nachweise

ORD-Eintrag
ord-73157f9dd6a64c56aedbbde165e7e130
Quelldatensatz
uspto-grants-2005_06
Patentnummer
US06911543B2

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