Ethyl bromoacetate → HCID 14622775, compound

HRID 1721924Notes

Reaction equation

HRID 1721924 reaction equation
[Cl:1][C:2]1[C:7]([Cl:8])=[C:6]([C:9]([C:11]2[N:15]([CH2:16][O:17][CH2:18][CH3:19])[N:14]=[CH:13][CH:12]=2)=[O:10])[CH:5]=[CH:4][C:3]=1[OH:20].Br[CH2:22][C:23]([O:25][CH2:26][CH3:27])=[O:24].C(=O)([O-])[O-].[K+].[K+]>CC(C)=O>[Cl:1][C:2]1[C:7]([Cl:8])=[C:6]([C:9]([C:11]2[N:15]([CH2:16][O:17][CH2:18][CH3:19])[N:14]=[CH:13][CH:12]=2)=[O:10])[CH:5]=[CH:4][C:3]=1[O:20][CH2:22][C:23]([O:25][CH2:26][CH3:27])=[O:24]

Participants

5

Reactant 3

HCID 7748Ethyl bromoacetateHCID 11430Potassium CarbonateHCID 14622774HCID 14622774, compound

Product 1

HCID 14622775HCID 14622775, compoundYield 88.9%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

1.67 g of 2,3-dichloro-4-(1-ethoxymethyl-5-pyrazolylcarbonyl)phenol, 1.15 g of ethyl bromoacetate and 1.68 g of potassium carbonate are added to 60 ml of acetone, and the mixture is refluxed for 1 hour. The reaction mixture is filtered and the filtrate is evaporated to remove solvent. The residue is dissolved in benzene, and the solution is treated with activated charcoal and evaporated to give an oil, which is then crystallized from isopropyl ether to give 1.89 g of ethyl [2,3-dichloro-4-(1-ethoxymethyl-5-pyrazolylcarbonyl)phenoxy]acetate.

Workup

  1. temperaturethe mixture is refluxed for 1 hour
  2. filtrationThe reaction mixture is filtered
  3. customthe filtrate is evaporated
  4. customto remove solvent
  5. dissolutionThe residue is dissolved in benzene
  6. additionthe solution is treated with activated charcoal
  7. customevaporated
  8. customto give an oil, which
  9. customis then crystallized from isopropyl ether

Sources & evidence

ORD record
ord-f2e4782b83334544bc4e8e6c0d8615b9
Source dataset
uspto-grants-1989_08
Patent number
US04853404

Reaction notes

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