Cesium carbonate → 1-(2,2-difluoroethyl)-4-nitro-1H-pyrazole

HRID 2089458Notes

Reaction equation

HRID 2089458 reaction equation
[N+:1]([C:4]1[CH:5]=[N:6][NH:7][CH:8]=1)([O-:3])=[O:2].[F:9][CH:10]([F:13])[CH2:11]I.C(=O)([O-])[O-].[Cs+].[Cs+]>C(#N)C.[Cl-].[NH4+]>[F:9][CH:10]([F:13])[CH2:11][N:6]1[CH:5]=[C:4]([N+:1]([O-:3])=[O:2])[CH:8]=[N:7]1

Participants

6

Reactant 3

HCID 10796Cesium carbonateHCID 163764-nitro-1H-pyrazoleHCID 38335651,1-Difluoro-2-iodoethane

Product 1

HCID 196146471-(2,2-difluoroethyl)-4-nitro-1H-pyrazoleYield 100.6%

Reagents, catalysts & solvents 2

HCID 6342AcetonitrileSolventHCID 25517Ammonium ChlorideSolvent

Conditions

Temperature
100 °C

Procedure

4-Nitro-1H-pyrazole (150 mg, 1.33 mmol) and 1,1-difluoro-2-iodo-ethane (509 mg, 2.65 mmol) were dissolved in acetonitrile (5 mL). Cesium carbonate (917 mg, 2.79 mml) was added and the mixture was heated at 100° C. for 40 min. After cooling down to room temperature, the reaction was diluted with sat. ammonium chloride and extracted with methylene chloride (3×). The combined organic layers were dried over sodium sulfate, filtered and the filtrate was concentrated to give 1-(2,2-difluoroethyl)-4-nitro-pyrazole (237 mg) as a light yellow solid.

Workup

  1. temperatureAfter cooling down to room temperature
  2. extractionextracted with methylene chloride (3×)
  3. dry with materialThe combined organic layers were dried over sodium sulfate
  4. filtrationfiltered
  5. concentrationthe filtrate was concentrated

Sources & evidence

ORD record
ord-fcd4f8b89df2447999f6b6d02a3cd7fd
Source dataset
uspto-grants-2013_05
Patent number
US08436001B2

Reaction notes

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