Hydrochloric Acid → 2-Fluoro-5-iodobenzoic acid

HRID 477869

Reaction equation

HRID 477869 reaction equation
[K].[F:2][C:3]1[CH:8]=[CH:7][C:6]([I:9])=[CH:5][C:4]=1[CH3:10].S(=O)(=O)(O)[O-:12].[Na+].Cl.[OH2:18]>C(Cl)Cl>[F:2][C:3]1[CH:8]=[CH:7][C:6]([I:9])=[CH:5][C:4]=1[C:10]([OH:12])=[O:18]

Participants

7

Reactant 5

HCID 313Hydrochloric AcidHCID 962WaterHCID 516919Sodium BisulfateHCID 5211782-Fluoro-5-iodotolueneHCID 5462222Potassium

Product 1

HCID 27789252-Fluoro-5-iodobenzoic acidYield 15%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To 8.1 g (51.3 mmol) of potassium permangante in 150 mL of water are added 5.0 g (21.1 mmol) of 2-fluoro-5-iodotoluene. The reaction mixture is heated at reflux for 4 hours. After being cooled to room temperature, the reaction mixture is poured into 250 mL of methylene chloride of sodium bisulfate, and 1N hydrochloric acid. The organic layer is separated, washed with water and dried over sodium sulfate. The solvent is removed in vacuo and the solid triturated with hexane to give 0.86 g (15%) of 2-fluoro-5-iodobenzoic acid as a white solid, m.p. 161°-163° C.

Workup

  1. temperatureThe reaction mixture is heated
  2. temperatureat reflux for 4 hours
  3. customThe organic layer is separated
  4. washwashed with water
  5. dry with materialdried over sodium sulfate
  6. customThe solvent is removed in vacuo
  7. customthe solid triturated with hexane

Sources & evidence

ORD record
ord-38325e46048d45498f4cbe61cff342e0
Source dataset
uspto-grants-1989_12
Patent number
US04889859

Linked notes

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