Citric Acid → 2-Fluoro-4-iodophenol

HRID 384095Notes

Reaction equation

HRID 384095 reaction equation
[F:1][C:2]1[CH:7]=[C:6]([I:8])[CH:5]=[CH:4][C:3]=1CC([O-])=O.[OH-].[Na+].C(O)(=O)CC(CC(O)=O)(C(O)=O)[OH:18]>CO.O>[F:1][C:2]1[CH:7]=[C:6]([I:8])[CH:5]=[CH:4][C:3]=1[OH:18]

Participants

6

Reactant 3

HCID 311Citric AcidHCID 14798Sodium HydroxideHCID 22240392HCID 22240392, compound

Product 1

HCID 145492232-Fluoro-4-iodophenol

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent

Procedure

To a solution of 2-fluoro-4-iodophenylacetate (500 mg) in methanol (3 ml) was added 1.07 ml of 2N aqueous sodium hydroxide. The reaction solution was stirred at room temperature for 40 minutes, followed by vacuum concentration of the reaction solution. The residue obtained was diluted with water, acidified with 10% aqueous citric acid to pH 4, then extracted with ethyl acetate, and dried over anhydrous magnesium sulfate. The solvent was distilled off under reduced pressure to afford the title compound as a colorless oil.

Workup

  1. customThe residue obtained
  2. extractionextracted with ethyl acetate
  3. dry with materialdried over anhydrous magnesium sulfate
  4. distillationThe solvent was distilled off under reduced pressure

Sources & evidence

ORD record
ord-7cf519730061449abeb7c23510eb4401
Source dataset
uspto-grants-2013_02
Patent number
US08367708B2

Reaction notes

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