Pyrazole → Ethyl 4-(1H-pyrazol-1-YL)benzoate

HRID 629358

Reaction equation

HRID 629358 reaction equation
F[C:2]1[CH:12]=[CH:11][C:5]([C:6]([O:8][CH2:9][CH3:10])=[O:7])=[CH:4][CH:3]=1.[NH:13]1[CH:17]=[CH:16][CH:15]=[N:14]1.C(=O)([O-])[O-].[K+].[K+]>CS(C)=O.O>[N:13]1([C:2]2[CH:12]=[CH:11][C:5]([C:6]([O:8][CH2:9][CH3:10])=[O:7])=[CH:4][CH:3]=2)[CH:17]=[CH:16][CH:15]=[N:14]1

Participants

6

Reactant 3

HCID 1048PyrazoleHCID 11430Potassium CarbonateHCID 67976Benzoic acid, 4-fluoro-, ethyl ester

Product 1

HCID 973146Ethyl 4-(1H-pyrazol-1-YL)benzoateYield 68.2%

Reagents, catalysts & solvents 2

HCID 679Dimethyl SulfoxideSolventHCID 962WaterSolvent

Conditions

Temperature
130 °C

Procedure

To a solution of ethyl 4-fluorobenzoate (105 g) in DMSO (250 mL) were added pyrazole (34.0 g) and potassium carbonate (138 g), and the mixture was heated with stirring at 130° C. for 16 hr. The reaction mixture was diluted with water, and the mixture was extracted with ethyl acetate. The organic layer was washed with saturated brine, and dried over anhydrous sodium sulfate, and the solvent was evaporated under reduced pressure to give the title compound (73.7 g).

Workup

  1. temperaturethe mixture was heated
  2. extractionthe mixture was extracted with ethyl acetate
  3. washThe organic layer was washed with saturated brine
  4. dry with materialdried over anhydrous sodium sulfate
  5. customthe solvent was evaporated under reduced pressure

Sources & evidence

ORD record
ord-3f1ef4f112fe47ecb3fb54a77d0bb99a
Source dataset
uspto-grants-2016_04
Patent number
US09315458B2

Linked notes

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