Bromoacetic Acid → [2,3-Dichloro-4-(1-ethoxymethyl-5-pyrazolylcarbonyl)phenoxy]acetic acid

HRID 1721925Notes

Reaction equation

HRID 1721925 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]([OH:25])=[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]([OH:25])=[O:24]

Participants

5

Reactant 3

HCID 6227Bromoacetic AcidHCID 11430Potassium CarbonateHCID 14622774HCID 14622774, compound

Product 1

HCID 9864296[2,3-Dichloro-4-(1-ethoxymethyl-5-pyrazolylcarbonyl)phenoxy]acetic acidYield 56.3%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

0.63 g of 2,3-dichloro-4-(1-ethoxymethyl-5-pyrazolylcarbonyl)phenol, 0.58 g of bromoacetic acid and 1.11 g of potassium carbonate are added to 40 ml of acetone, and the mixture is refluxed for 48 hours. The reaction mixture is concentrated to remove solvent, and water is added to the residue. The aqueous mixture is washed with ethyl acetate, acidified with 10% hydrochloric acid and then extracted with ethyl acetate. The extract is washed with a saturated sodium chloride solution, dried and evaporated to remove solvent. The residue is crystallized with water, and the crystals are separated by filtration, washed successively with water and isopropyl ether, and dried to give 0.42 g of [2,3-dichloro-4-(1-ethoxymethyl-5-pyrazolylcarbonyl)phenoxy]acetic acid.

Workup

  1. temperaturethe mixture is refluxed for 48 hours
  2. concentrationThe reaction mixture is concentrated
  3. customto remove solvent, and water
  4. additionis added to the residue
  5. washThe aqueous mixture is washed with ethyl acetate
  6. extractionextracted with ethyl acetate
  7. washThe extract is washed with a saturated sodium chloride solution
  8. customdried
  9. customevaporated
  10. customto remove solvent
  11. customThe residue is crystallized with water
  12. customthe crystals are separated by filtration
  13. washwashed successively with water and isopropyl ether
  14. customdried

Sources & evidence

ORD record
ord-bae290b93c5c434d85ea6ad0188b6633
Source dataset
uspto-grants-1989_08
Patent number
US04853404

Reaction notes

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