Ethyl bromoacetate → (4-Chloro-5-methyl-3-trifluoromethyl-pyrazol-1-yl)-acetic acid
Reaction equation
[Cl:1][C:2]1[C:3]([C:8]([F:11])([F:10])[F:9])=[N:4][NH:5][C:6]=1[CH3:7].Br[CH2:13][C:14]([O:16]CC)=[O:15].C(=O)([O-])[O-].[K+].[K+]>CN(C=O)C.O>[Cl:1][C:2]1[C:3]([C:8]([F:9])([F:11])[F:10])=[N:4][N:5]([CH2:13][C:14]([OH:16])=[O:15])[C:6]=1[CH3:7]Participants
6
Reactant 3
Product 1
Reagents, catalysts & solvents 2
Conditions
- Temperature
- 55 °C
Procedure
To a solution of 4-chloro-5-methyl-3-(trifluoromethyl)pyrazole (15 g, 81.3 mmol) in DMF (82 mL) was added ethyl 2-bromoacetate (13.6 g, 81.3 mmol) and potassium carbonate (12.4 g, 89.4 mmol). The mixture was heated at 55° C. for 10 hours with stirring. After cooling to room temperature, the reaction mixture was diluted with water (100 mL) and extracted with ethyl acetate (3×150 mL). The combined organic layers were washed with brine, dried (Na2SO4), filtered, and concentrated in vacuo. The crude residue was purified by flash chromatography (SiO2, 0-30% ethyl acetate in hexanes) to afford the desired product (18.5 g, 68.4 mmol, 84%).
Workup
- temperatureAfter cooling to room temperature
- extractionextracted with ethyl acetate (3×150 mL)
- washThe combined organic layers were washed with brine
- dry with materialdried (Na2SO4)
- filtrationfiltered
- concentrationconcentrated in vacuo
- customThe crude residue was purified by flash chromatography (SiO2, 0-30% ethyl acetate in hexanes)
Sources & evidence
- ORD record
- ord-f4dba391d020462b9fe73839d26908f6
- Source dataset
- uspto-grants-2015_11
- Patent number
- US09181241B2
Reaction notes
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