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Dimethylformamide → 1-(3-methyl-4-nitrobenzyl)-4-pentafluoroethyl-3-trifluoromethyl-1H-pyrazole

HRID 2243250
Notes
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Reaction equation

HRID 2243250 reaction equation
I[C:2]1[C:3]([C:18]([F:21])([F:20])[F:19])=[N:4][N:5]([CH2:7][C:8]2[CH:13]=[CH:12][C:11]([N+:14]([O-:16])=[O:15])=[C:10]([CH3:17])[CH:9]=2)[CH:6]=1.I[C:23]([F:29])([F:28])[C:24]([F:27])([F:26])[F:25].CN(C=O)C>C(OCC)(=O)C.[Cu]>[CH3:17][C:10]1[CH:9]=[C:8]([CH:13]=[CH:12][C:11]=1[N+:14]([O-:16])=[O:15])[CH2:7][N:5]1[CH:6]=[C:2]([C:23]([F:29])([F:28])[C:24]([F:27])([F:26])[F:25])[C:3]([C:18]([F:21])([F:20])[F:19])=[N:4]1
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 3

HCID 6228DimethylformamideHCID 9636IodopentafluoroethaneHCID 592104224-iodo-1-(3-methyl-4-nitrobenzyl)-3-trifluoromethyl-1H-pyrazole

Product 1

HCID 866171361-(3-methyl-4-nitrobenzyl)-4-pentafluoroethyl-3-trifluoromethyl-1H-pyrazoleYield 68.8%

Reagents, catalysts & solvents 2

HCID 23978Copper
Catalyst
HCID 8857Ethyl AcetateSolvent

Conditions

Temperature
132.5 °C

Procedure

4-Iodo-1-(3-methyl-4-nitrobenzyl)-3-trifluoromethyl-1H-pyrazole (2.06 g), copper powder (0.95 g), iodopentafluoroethane (4.92 g) and DMF (13 ml) were set in an autoclave and heated and stirred for 8 hours, maintaining the inside temperature of 130-135° C. After cooling to room temperature, the reaction mixture was diluted with ethyl acetate (50 ml) and an insoluble matter was filtered with Celite and washed with ethyl acetate. The filtrate was concentrated under the reduced pressure and the obtained residue was purified by silica gel column chromatography to obtain 1-(3-methyl-4-nitrobenzyl)-4-pentafluoroethyl-3-trifluoromethyl-1H-pyrazole (1.39 g)

Workup

  1. temperatureheated
  2. temperatureAfter cooling to room temperature
  3. filtrationan insoluble matter was filtered with Celite
  4. washwashed with ethyl acetate
  5. concentrationThe filtrate was concentrated under the reduced pressure
  6. customthe obtained residue was purified by silica gel column chromatography

Sources & evidence

ORD record
ord-5acd460d64454c66ab694589d46f2fd7
Source dataset
uspto-grants-2010_03
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US07674807B2

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes