Citric Acid → HCID 69061883, compound

HRID 733132Notes

Reaction equation

HRID 733132 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([N:8]2[CH:12]=[C:11]([C:13]([O:15]CC)=[O:14])[C:10]([C:18]([F:21])([F:20])[F:19])=[N:9]2)[CH:5]=[CH:6][CH:7]=1.ClC1C=CC=CC=1B(O)O.C(=O)([O-])[O-].[Na+].[Na+].[OH-].[Na+].C(O)(=O)CC(CC(O)=O)(C(O)=O)O>C(O)CC.C([O-])(=O)C.[Pd+2].C([O-])(=O)C.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.O>[Br:1][C:2]1[CH:3]=[C:4]([N:8]2[CH:12]=[C:11]([C:13]([OH:15])=[O:14])[C:10]([C:18]([F:19])([F:20])[F:21])=[N:9]2)[CH:5]=[CH:6][CH:7]=1

Participants

10

Reactant 5

HCID 311Citric AcidHCID 10340Sodium CarbonateHCID 14798Sodium HydroxideHCID 27343222-Chlorophenylboronic acidHCID 69062179HCID 69062179, compound

Product 1

HCID 69061883HCID 69061883, compoundYield 87.6%

Reagents, catalysts & solvents 4

HCID 11776TriphenylphosphineCatalystHCID 167845palladium(II) acetateCatalystHCID 962WaterSolventHCID 10311-PropanolSolvent

Procedure

To a solution of ethyl 1-(3-bromophenyl)-3-(trifluoromethyl)-1H-pyrazole-4-carboxylate (0.5 g, 1.37 mmol) and 2-chlorophenylboronic acid (0.28 g, 1.78 mmol) in n-propanol:water (2.35 ml:0.482 ml) mixture were added palladium acetate (0.005 g), triphenylphosphine (0.016 g) and 2N sodium carbonate (0.497 ml). The mixture was refluxed for 16 hours. A 2N NaOH (1.5 ml) was then added and refluxing continued for an additional 2 hours. The reaction was cooled, acidified with 10% citric acid and extracted with ethyl acetate. The organic phase was washed with brine, dried over sodium sulfate, filtered and concentrated to give 0.402 g of 1-(3-bromophenyl)-3-(trifluoromethyl)-1H-pyrazole-4-carboxylic acid.

Workup

  1. temperatureThe mixture was refluxed for 16 hours
  2. temperaturerefluxing
  3. temperatureThe reaction was cooled
  4. extractionextracted with ethyl acetate
  5. washThe organic phase was washed with brine
  6. dry with materialdried over sodium sulfate
  7. filtrationfiltered
  8. concentrationconcentrated

Sources & evidence

ORD record
ord-9021aa1878514bd88f53dfdd04bff832
Source dataset
uspto-grants-2009_09
Patent number
US07589116B2

Reaction notes

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