Hydrochloric Acid → 2-Chloro-4,5-difluorobenzoic acid

HRID 974659Notes

Reaction equation

HRID 974659 reaction equation
C[C:2]([C:4]1[C:9]([Cl:10])=[CH:8][C:7]([F:11])=[C:6]([F:12])[CH:5]=1)=[O:3].Cl[O-:14].[Na+].Cl>C(Cl)Cl>[Cl:10][C:9]1[CH:8]=[C:7]([F:11])[C:6]([F:12])=[CH:5][C:4]=1[C:2]([OH:3])=[O:14]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 27364892'-Chloro-4',5'-difluoroacetophenoneHCID 23665760Sodium Hypochlorite

Product 1

HCID 7371712-Chloro-4,5-difluorobenzoic acidYield 85.1%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To 19.1 g (0.1 mol) of 2-chloro-4,5-difluoroacetophenone, 280.4 g (0.4 mol) of a 12% sodium hypochlorite aqueous solution was added, and the mixture was reacted under reflux for 4 hours. After cooling, concentrated hydrochloric acid was dropwise added thereto until the pH became 1. The formed white crystals were dissolved in methylene chloride and separated from the aqueous phase. The separated aqueous phase was extracted twice with methylene chloride, and the extracts were added to the oil phase. Then, the solvent was distilled off to obtain 16.4 g (yield: 85.1%) of 2-chloro-4,5-difluorobenzoic acid as white crystal.

Workup

  1. customthe mixture was reacted
  2. temperatureunder reflux for 4 hours
  3. temperatureAfter cooling
  4. customseparated from the aqueous phase
  5. extractionThe separated aqueous phase was extracted twice with methylene chloride
  6. additionthe extracts were added to the oil phase
  7. distillationThen, the solvent was distilled off

Sources & evidence

ORD record
ord-7033b73d738e4bb29fffa2f01965f0e4
Source dataset
uspto-grants-1991_11
Patent number
US05068449

Reaction notes

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