Citric Acid → 1-(3-Bromophenyl)-1H-pyrazole-3-carboxylic acid

HRID 733122Notes

Reaction equation

HRID 733122 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([N:8]2[C:12](C)=[CH:11][C:10]([C:14]([O:16]CC)=[O:15])=[N:9]2)[CH:5]=[CH:6][CH:7]=1.C(O)(=O)CC(CC(O)=O)(C(O)=O)O>[OH-].[Na+]>[Br:1][C:2]1[CH:3]=[C:4]([N:8]2[CH:12]=[CH:11][C:10]([C:14]([OH:16])=[O:15])=[N:9]2)[CH:5]=[CH:6][CH:7]=1

Participants

4

Reactant 2

HCID 311Citric AcidHCID 18549277Ethyl 1-(3-bromophenyl)-5-methyl-1h-pyrazole-3-carboxylate

Product 1

HCID 431246391-(3-Bromophenyl)-1H-pyrazole-3-carboxylic acidYield 89%

Reagents, catalysts & solvents 1

HCID 14798Sodium HydroxideSolvent

Procedure

A solution of ethyl 1-(3-bromophenyl)-5-methyl-1H-pyrazole-3-carboxylate (4.28 g, 17.8 mmol) in 2N NaOH (17.85 ml) was refluxed for 16 hours. The reaction was cooled to room temperature, neutralized with 10% citric acid and extracted with ethylacetate. The organic phase was washed with brine, dried over sodium sulfate, filtered and concentrated to give 1-(3-bromophenyl)-1H-pyrazole-3-carboxylic acid (3.29 g, 89%).

Workup

  1. extractionextracted with ethylacetate
  2. washThe organic phase was washed with brine
  3. dry with materialdried over sodium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-867a3a2d1ec54f9a8f56cbc6eae1db2d
Source dataset
uspto-grants-2009_09
Patent number
US07589116B2

Reaction notes

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