Potassium Carbonate → (((2-chloro-5-(4-chloro-1-methyl-5-(trifluoromethyl)-1H-pyrazol-3-yl)-4-fluorophenyl)methyl)thio)acetic acid, ethyl ester

HRID 1440149Notes

Reaction equation

HRID 1440149 reaction equation
Br[CH2:2][C:3]1[C:4]([Cl:21])=[CH:5][C:6]([F:20])=[C:7]([C:9]2[C:13]([Cl:14])=[C:12]([C:15]([F:18])([F:17])[F:16])[N:11]([CH3:19])[N:10]=2)[CH:8]=1.[SH:22][CH2:23][C:24]([O:26][CH2:27][CH3:28])=[O:25].C([O-])([O-])=O.[K+].[K+]>CC(C)=O>[Cl:21][C:4]1[CH:5]=[C:6]([F:20])[C:7]([C:9]2[C:13]([Cl:14])=[C:12]([C:15]([F:18])([F:17])[F:16])[N:11]([CH3:19])[N:10]=2)=[CH:8][C:3]=1[CH2:2][S:22][CH2:23][C:24]([O:26][CH2:27][CH3:28])=[O:25]

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 12185Ethyl ThioglycolateHCID 194367643-[5-(bromomethyl)-4-chloro-2-fluorophenyl]-4-chloro-1-methyl-5-(trifluoromethyl)-1H-pyrazole

Product 1

HCID 86747525(((2-chloro-5-(4-chloro-1-methyl-5-(trifluoromethyl)-1H-pyrazol-3-yl)-4-fluorophenyl)methyl)thio)acetic acid, ethyl esterYield 96%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

A mixture of 1.62 g (4.0 mmole) 3-[5-(bromomethyl)-4-chloro-2-fluorophenyl]-4-chloro-1-methyl-5-(trifluoromethyl)-1H-pyrazole, 0.44 mL ethyl mercaptoacetate and 0.55 g K2CO3 was slurried in 25 mL of acetone. The reaction mixture was allowed to stir at room temperature overnight. After dilution with 100 mL of cold water, the mixture was extracted with ethyl acetate, the organic extracts washed with water, dried with MgSO4 and concentrated in vacuo. The residue was purified by chromatography to afford 1.7 g (96%) of (((2-chloro-5-(4-chloro-1-methyl-5-(trifluoromethyl) -1H-pyrazol-3-yl) -4-fluorophenyl)methyl)thio)acetic acid, ethyl ester as a white solid; mp 63° C.

Workup

  1. extractionAfter dilution with 100 mL of cold water, the mixture was extracted with ethyl acetate
  2. washthe organic extracts washed with water
  3. dry with materialdried with MgSO4
  4. concentrationconcentrated in vacuo
  5. customThe residue was purified by chromatography

Sources & evidence

ORD record
ord-6cc60ae99ed44f579a97e1b6812b6ac1
Source dataset
uspto-grants-1996_03
Patent number
US05496956

Reaction notes

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