Iodine → 6-Chloro-2-iodo-3-hydroxypyridine

HRID 595644Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 595644
[Cl:1][C:2]1[N:7]=[CH:6][C:5]([OH:8])=[CH:4][CH:3]=1.C([O-])([O-])=O.[Na+].[Na+].[I:15]I.[O-]S([O-])(=S)=O.[Na+].[Na+]>O>[Cl:1][C:2]1[N:7]=[C:6]([I:15])[C:5]([OH:8])=[CH:4][CH:3]=1

Komponenten

6

Edukt 4

HCID 807IodineHCID 10340Sodium CarbonateHCID 24477Sodium ThiosulfateHCID 8198212-Chloro-5-hydroxypyridine

Produkt 1

HCID 234331586-Chloro-2-iodo-3-hydroxypyridineAusbeute 71 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 962WaterLösungsmittel

Versuchsvorschrift

6-chloropyridin-3-ol (5.0 g, 38.60 mmol) was dissolved in water (50 mL) and placed under an N2 atmosphere. Na2CO3 (8.2 g, 77.37 mmol) was added followed by iodine (9.8 g, 38.81 mmol). The reaction mixture was stirred at room temperature for 2 h. The mixture was poured into 1 M Na2S2O3 and extracted with EtOAc. The combined organic phases were washed with brine, dried over Na2SO4 and concentrated to give the product of 6-chloro-2-iodopyridin-3-ol (7.0 g, yield: 70.9%). 1H-NMR (CDCl3, 400 MHz) δ 7.17 (d, J=8.4 Hz, 1H), 7.06 (d, J=8.4 Hz, 1H). MS (M+H)+: 256/258.

Aufarbeitung

  1. extractionextracted with EtOAc
  2. washThe combined organic phases were washed with brine
  3. dry with materialdried over Na2SO4
  4. concentrationconcentrated

Quellen und Nachweise

ORD-Eintrag
ord-876bb7ff644f4e9c8ee736b9e5e6ff6e
Quelldatensatz
uspto-grants-2016_01
Patentnummer
US09243002B2

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