1,1,2,2-Tetrafluoroethyl iodide → 3-pentafluoroethyl-4-(1,1,2,2-tetrafluoroethyl)-1H-pyrazole

HRID 2243280Notes

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

Participants

Conditions

Temperature: 122.5 °C

Procedure

4-Iodo-3-pentafluoroethyl-1H-pyrazole (6.24 g), copper powder (3.81 g), Iodo-1,1,2,2-tetrafluoroethane (9.12 g) and DMF (30 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-pentafluoroethyl-4-(1,1,2,2-tetrafluoroethyl)-1H-pyrazole (0.60 g), bp. 125-135° C./20 mbar.

Workup

temperatureheated
temperatureAfter cooling to room temperature
filtrationthe insoluble material was filtered off through Celite
washwashed with diethyl ether
additionThe filtrate was diluted with water
extractionextracted with diethyl ether
washThe organic phase was washed with water
dry with materialdried over sodium sulfate
concentrationconcentrated under the reduced pressure
distillationThe crude product was distilled under reduced pressure

Sources & evidence

ORD record: ord-e2f53f7ccd934c58b63d46216c3a8ae5
Source dataset: uspto-grants-2010_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07674807B2

Reaction notes

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