Iodopentafluoroethane → HCID 178506327, compound

HRID 2243281Notes

Reaction equation

HRID 2243281 reaction equation
I[C:2]1[C:3]([C:7]([F:13])([F:12])[C:8]([F:11])([F:10])[F:9])=[N:4][NH:5][CH:6]=1.I[C:15]([F:21])([F:20])[C:16]([F:19])([F:18])[F:17]>[Cu].CN(C=O)C>[F:12][C:7]([F:13])([C:3]1[C:2]([C:15]([F:21])([F:20])[C:16]([F:19])([F:18])[F:17])=[CH:6][NH:5][N:4]=1)[C:8]([F:11])([F:10])[F:9]

Participants

5

Reactant 2

HCID 9636IodopentafluoroethaneHCID 178506332HCID 178506332, compound

Product 1

HCID 178506327HCID 178506327, compoundYield 9.9%

Reagents, catalysts & solvents 2

HCID 23978CopperCatalystHCID 6228DimethylformamideSolvent

Conditions

Temperature
122.5 °C

Procedure

4-Iodo-3-pentafluoroethyl-1H-pyrazole (12.48 g), copper powder (7.63 g), iodopentafluoroethane (29.50 g) and DMF (60 ml) were set in an autoclave and heated and stirred for 8 hours, maintaining the inside temperature of 120-125° C. After cooling to room temperature, the insoluble material was filtered off through Celite and washed with diethyl ether. The filtrate was diluted with water and extracted with diethyl ether. The organic phase was washed with water and dried over sodium sulfate, and concentrated under the reduced pressure. The crude product was distilled under reduced pressure to obtain 3,4-bis-pentafluoroethyl-1H-pyrazole (1.20 g), bp. 110-115° C./20 mbar.

Workup

  1. temperatureheated
  2. temperatureAfter cooling to room temperature
  3. filtrationthe insoluble material was filtered off through Celite
  4. washwashed with diethyl ether
  5. additionThe filtrate was diluted with water
  6. extractionextracted with diethyl ether
  7. washThe organic phase was washed with water
  8. dry with materialdried over sodium sulfate
  9. concentrationconcentrated under the reduced pressure
  10. distillationThe crude product was distilled under reduced pressure

Sources & evidence

ORD record
ord-e303a7e8bf0b4a68b5db9d22217ccab1
Source dataset
uspto-grants-2010_03
Patent number
US07674807B2

Reaction notes

Loading…