Potassium Hydroxide → 4-bromo-5-(4-chlorophenyl)-1-(2,4-dichlorophenyl)-1H-pyrazole-3-carboxylic acid

HRID 254818Notes

Reaction equation

HRID 254818 reaction equation
[Br:1][C:2]1[C:3]([C:22]([O:24]CC)=[O:23])=[N:4][N:5]([C:14]2[CH:19]=[CH:18][C:17]([Cl:20])=[CH:16][C:15]=2[Cl:21])[C:6]=1[C:7]1[CH:12]=[CH:11][C:10]([Cl:13])=[CH:9][CH:8]=1.[OH-].[K+]>CO>[Br:1][C:2]1[C:3]([C:22]([OH:24])=[O:23])=[N:4][N:5]([C:14]2[CH:19]=[CH:18][C:17]([Cl:20])=[CH:16][C:15]=2[Cl:21])[C:6]=1[C:7]1[CH:12]=[CH:11][C:10]([Cl:13])=[CH:9][CH:8]=1

Participants

4

Reactant 2

HCID 14797Potassium HydroxideHCID 10939684Ethyl 4-bromo-5-(4-chlorophenyl)-1-(2,4-dichlorophenyl)-1H-pyrazole-3-carboxylate

Product 1

HCID 668445074-bromo-5-(4-chlorophenyl)-1-(2,4-dichlorophenyl)-1H-pyrazole-3-carboxylic acidYield 97.2%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
100 °C

Procedure

To a solution of ethyl 4-bromo-5-(4-chlorophenyl)-1-(2,4-dichlorophenyl)-1H-pyrazole-3-carboxylate (3.5 g, 7.37 mmol) in methanol (50 ml) at room temperature was added potassium hydroxide (830 mg, 14.8 mmol) in one portion. The reaction mixture was warmed to 100° C. and then stirred for 5 hours. The resulting solution was cooled down to room temperature and then evaporated the volatile solvent. The residue was acidified with 10% hydrochloric acid and then filtered using water and hexane. The filtrated solid was dried under vacuum to obtain the title compound (3.2 g, 97%) as pale yellow solid.

Workup

  1. temperatureThe resulting solution was cooled down to room temperature
  2. customevaporated the volatile solvent
  3. filtrationfiltered
  4. customThe filtrated solid was dried under vacuum

Sources & evidence

ORD record
ord-4ff22b9913914b7b8d228a6b61602a67
Source dataset
uspto-grants-2011_01
Patent number
US07875647B2

Reaction notes

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