Ethyl bromoacetate → ethyl 4-phenyl-1H-pyrazole-1-acetate

HRID 477465Notes

Reaction equation

HRID 477465 reaction equation
[H-].[Na+].[C:3]1([C:9]2[CH:10]=[N:11][NH:12][CH:13]=2)[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1.Br[CH2:15][C:16]([O:18][CH2:19][CH3:20])=[O:17]>CN(C=O)C>[C:3]1([C:9]2[CH:10]=[N:11][N:12]([CH2:15][C:16]([O:18][CH2:19][CH3:20])=[O:17])[CH:13]=2)[CH:4]=[CH:5][CH:6]=[CH:7][CH:8]=1

Participants

5

Reactant 3

HCID 7748Ethyl bromoacetateHCID 24758Sodium hydrideHCID 1391064-Phenylpyrazole

Product 1

HCID 14772168ethyl 4-phenyl-1H-pyrazole-1-acetate

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a slurry of 3.0g (0.075 mol) of sodium hydride in 30 mL of DMF at room temperature was added 10g (0.069 mol) of 4-phenyl-1H-pyrazole of example 1. The mixture was stirred 1 hr and 7.8 mL (0.07 mol) of ethyl bromoacetate was added with cooling. The reaction was stirred 3 hr at room temperature, briefly at 100° C. and was poured onto ice. The product was filtered off, rinsed with water, dried, and washed with hexane to yield 14.0g of ethyl 4-phenyl-1H-pyrazole-1-acetate.

Workup

  1. temperaturewith cooling
  2. stirringThe reaction was stirred 3 hr at room temperature, briefly at 100° C.
  3. additionwas poured onto ice
  4. filtrationThe product was filtered off
  5. washrinsed with water
  6. customdried
  7. washwashed with hexane

Sources & evidence

ORD record
ord-63eb4457df0e43e4991ecee5b81c8cc3
Source dataset
uspto-grants-1989_12
Patent number
US04888352

Reaction notes

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