Hydrochloric Acid → 4-Chloro-2-fluoro-3-iodoaniline

HRID 1811538

Reaktionsgleichung

Reaktionsgleichung von HRID 1811538
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([NH:8]C(=O)C)=[C:4]([F:12])[C:3]=1[I:13].Cl>CO>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([NH2:8])=[C:4]([F:12])[C:3]=1[I:13]

Komponenten

4

Edukt 2

HCID 313Hydrochloric AcidHCID 68997639N-(4-chloro-2-fluoro-3-iodophenyl)acetamide

Produkt 1

HCID 688233204-Chloro-2-fluoro-3-iodoaniline

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 887MethanolLösungsmittel

Versuchsvorschrift

To a mixture of N-(4-chloro-2-fluoro-3-iodophenyl)acetamide (20.0 g, 64 mmol) in MeOH (80 mL) is added concentrated HCl (60 mL). The mixture is stirred at reflux for 18 hours before cooling to room temperature and removal of the solvent under reduced pressure while maintaining the water bath below 45° C. The residue is cooled with an ice bath and a 1N NaOH solution is added to adjust the pH between 9 and 10. The aqueous phase is extracted with ether and dried over MgSO4. The solvent is removed and the residue is purified through a flash chromatographic column with a gradient of hexanes/ether to give 4-chloro-2-fluoro-3-iodoaniline.

Aufarbeitung

  1. temperatureat reflux for 18 hours
  2. customremoval of the solvent under reduced pressure
  3. temperaturewhile maintaining the water bath below 45° C
  4. temperatureThe residue is cooled with an ice bath
  5. additiona 1N NaOH solution is added
  6. extractionThe aqueous phase is extracted with ether
  7. dry with materialdried over MgSO4
  8. customThe solvent is removed
  9. customthe residue is purified through a flash chromatographic column with a gradient of hexanes/ether

Quellen und Nachweise

ORD-Eintrag
ord-b0b2273db167429d93c274adcb4e7a31
Quelldatensatz
uspto-grants-2013_01
Patentnummer
US08362294B2

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