Ethyl bromoacetate → ethyl 5-chloro-3-(trifluoromethyl)-1H-pyrazole-1-acetate

HRID 2043745Notes

Reaction equation

HRID 2043745 reaction equation
[Cl:1][C:2]1[NH:6][N:5]=[C:4]([C:7]([F:10])([F:9])[F:8])[CH:3]=1.C(=O)([O-])[O-].[K+].[K+].Br[CH2:18][C:19]([O:21][CH2:22][CH3:23])=[O:20]>CN(C)C=O.C(OCC)(=O)C>[Cl:1][C:2]1[N:6]([CH2:18][C:19]([O:21][CH2:22][CH3:23])=[O:20])[N:5]=[C:4]([C:7]([F:10])([F:9])[F:8])[CH:3]=1

Participants

6

Reactant 3

HCID 7748Ethyl bromoacetateHCID 11430Potassium CarbonateHCID 1785061975-chloro-3-(trifluoromethyl)-1H-pyrazole2×

Product 1

HCID 66016896ethyl 5-chloro-3-(trifluoromethyl)-1H-pyrazole-1-acetateYield 29.8%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

A suspension of 5-chloro-3-trifluoromethyl-1H-pyrazole (2.1 g, 12.3 mmol) (i.e. the product of Example 13, Step C), potassium carbonate (3.6 g, 26 mmol) in N,N-dimethylformamide (20 mL) was treated with ethyl bromoacetate (2.1 mL, 18.8 mmol) and the reaction mixture was stirred at ambient temperature for 12 h. The reaction mixture was diluted with ethyl acetate, washed with water, and dried over MgSO4. The reaction mixture was filtered and concentrated under reduced pressure. The crude product was purified by silica gel chromatography using 0-50% ethyl acetate in hexanes as eluant to give 940 mg of the title compound.

Workup

  1. washwashed with water
  2. dry with materialdried over MgSO4
  3. filtrationThe reaction mixture was filtered
  4. concentrationconcentrated under reduced pressure
  5. customThe crude product was purified by silica gel chromatography

Sources & evidence

ORD record
ord-0ed21987bd8b4357ab718ce75638c089
Source dataset
uspto-grants-2013_11
Patent number
US08586611B2

Reaction notes

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