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Sodium percarbonate → 3,4-Difluorobenzoic acid

HRID 374618
Notes
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Reaction equation

HRID 374618 reaction equation
[C:1]([O-:4])([O-])=[O:2].C([O-])([O-])=O.OO.OO.OO.[Na+].[Na+].[Na+].[Na+].[F:19][C:20]1[CH:21]=[C:22]([CH:31]=[CH:32][C:33]=1[F:34])C(C1C=CC=CC=1)=O>FC(F)(F)C(O)=O>[F:19][C:20]1[CH:21]=[C:22]([CH:31]=[CH:32][C:33]=1[F:34])[C:1]([OH:4])=[O:2]
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

4

Reactant 2

HCID 159762Sodium percarbonateHCID 5699083,4-Difluorobenzophenone

Product 1

HCID 991663,4-Difluorobenzoic acidYield 95.5%

Reagents, catalysts & solvents 1

HCID 6422Trifluoroacetic acidSolvent

Procedure

2.5 g of sodium percarbonate were added over 1 h to a solution of 2.2 g (10 mmol) of 3,4-difluorobenzophenone and 20 ml of trifluoroacetic acid (0° C.) and the temperature was then allowed to rise to 20° C. The mixture was stirred for 16 h at this temperature and 50 g of ice were then added. The mixture was subsequently extracted twice with dichloromethane and the organic phases were washed (NaHCO3) until the washings were neutral. The solvent was then removed. Working-up as described in Example 22 gave 1.2 g (7.6 mmol, 76%) of 3,4-difluorobenzoic acid, which can be obtained analytically pure from water (melting point 113°-120.5° C.).

Workup

  1. customto rise to 20° C
  2. additionwere then added
  3. extractionThe mixture was subsequently extracted twice with dichloromethane
  4. washthe organic phases were washed (NaHCO3) until the washings
  5. customThe solvent was then removed

Sources & evidence

ORD record
ord-3a540bda32044b3891e823049d0d41e1
Source dataset
uspto-grants-1996_01
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US05481032

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes