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

HRID 2044200

Reaction equation

HRID 2044200 reaction equation
[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]

Participants

4

Reactant 2

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

Product 1

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

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

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.

Workup

  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

Sources & evidence

ORD record
ord-3dcf60b1c1024b87a6cc0c73f9076183
Source dataset
uspto-grants-2013_11
Patent number
US08586782B2

Linked notes

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