Potassium Carbonate → Allyl 2-(3-(2,6-difluorophenyl)pyrazol-1-yl)acetate

HRID 230097Notes

Reaction equation

HRID 230097 reaction equation
C(=O)([O-])[O-].[K+].[K+].[F:7][C:8]1[CH:13]=[CH:12][CH:11]=[C:10]([F:14])[C:9]=1[C:15]1[CH:19]=[CH:18][NH:17][N:16]=1.Br[CH2:21][C:22]([O:24][CH2:25][CH:26]=[CH2:27])=[O:23]>C(#N)C>[F:7][C:8]1[CH:13]=[CH:12][CH:11]=[C:10]([F:14])[C:9]=1[C:15]1[CH:19]=[CH:18][N:17]([CH2:21][C:22]([O:24][CH2:25][CH:26]=[CH2:27])=[O:23])[N:16]=1

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 527610Prop-2-enyl 2-bromoacetateHCID 178505719HCID 178505719, compound

Product 1

HCID 22169508Allyl 2-(3-(2,6-difluorophenyl)pyrazol-1-yl)acetateYield 97.1%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

Potassium carbonate (1.53 g) was added to an acetonitrile (10 mL) solution of 3-(2,6-difluorophenyl)-pyrazole (1 g) and allyl 2-bromoacetate (1.49 g), and refluxed for 3 hours. The resulting product was extracted with acetate and diluted hydrochloric acid added thereto at room temperature. The organic layer was dried over anhydrous magnesium sulfate and concentrated, and the resulting concentrate was purified through silica gel column chromatography (chloroform) to obtain allyl 2-(3-(2,6-difluorophenyl)pyrazol-1-yl)acetate (1.5 g).

Workup

  1. temperaturerefluxed for 3 hours
  2. extractionThe resulting product was extracted with acetate and diluted hydrochloric acid
  3. additionadded
  4. customat room temperature
  5. dry with materialThe organic layer was dried over anhydrous magnesium sulfate
  6. concentrationconcentrated
  7. concentrationthe resulting concentrate
  8. customwas purified through silica gel column chromatography (chloroform)

Sources & evidence

ORD record
ord-7dad8af06f064827b13d3af25b5e7366
Source dataset
uspto-grants-2009_07
Patent number
US07566683B2

Reaction notes

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