Iodopentafluoroethane → 1-(3-methyl-4-nitrophenyl)-4-pentafluoroethyl-1H-pyrazole

HRID 2243272Notes

Reaction equation

I[C:2]1[CH:3]=[N:4][N:5]([C:7]2[CH:12]=[CH:11][C:10]([N+:13]([O-:15])=[O:14])=[C:9]([CH3:16])[CH:8]=2)[CH:6]=1.I[C:18]([F:24])([F:23])[C:19]([F:22])([F:21])[F:20]>[Cu].CS(C)=O>[CH3:16][C:9]1[CH:8]=[C:7]([N:5]2[CH:6]=[C:2]([C:18]([F:24])([F:23])[C:19]([F:22])([F:21])[F:20])[CH:3]=[N:4]2)[CH:12]=[CH:11][C:10]=1[N+:13]([O-:15])=[O:14]

Participants

Conditions

Temperature: 100 °C

Procedure

4-Iodo-1-(3-methyl-4-nitrophenyl)-1H-pyrazole (1.98 g), copper powder (1.14 g), iodopentafluoroethane (8.85 g) and DMSO (9 ml) were set in an autoclave and heated and stirred for 8 hours, maintaining the inside temperature of 100° C. After finishing the reaction, the reaction mixture was poured into ice water and an insoluble matter was filtered with Celite, and then, it was extracted with ethyl acetate. The extracted solution was washed with water and dried with anhydrous sodium sulfate. After distilling off the solvent, the obtained residue was purified by silica gel column chromatography to obtain 1-(3-methyl-4-nitrophenyl)-4-pentafluoroethyl-1H-pyrazole (0.72 g).

Workup

temperatureheated
customthe reaction
filtrationan insoluble matter was filtered with Celite
extractionit was extracted with ethyl acetate
washThe extracted solution was washed with water
dry with materialdried with anhydrous sodium sulfate
distillationAfter distilling off the solvent
customthe obtained residue was purified by silica gel column chromatography

Sources & evidence

ORD record: ord-f1b130b13319425789eb848c6605c4b8
Source dataset: uspto-grants-2010_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07674807B2

Reaction notes

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