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1-(2,3-dichlorophenyl)-5-iodo-3-(trifluoromethyl)-1H-pyrazole → 1-(2,3-dichlorophenyl)-3-(trifluoromethyl)-1H-pyrazole-5-carbonitrile

HRID 1842885
Notes
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Reaction equation

HRID 1842885 reaction equation
[Cl:1][C:2]1[C:7]([Cl:8])=[CH:6][CH:5]=[CH:4][C:3]=1[N:9]1[C:13](I)=[CH:12][C:11]([C:15]([F:18])([F:17])[F:16])=[N:10]1.[C:19]([Cu])#[N:20]>CN1C(=O)CCC1>[Cl:1][C:2]1[C:7]([Cl:8])=[CH:6][CH:5]=[CH:4][C:3]=1[N:9]1[C:13]([C:19]#[N:20])=[CH:12][C:11]([C:15]([F:18])([F:17])[F:16])=[N:10]1
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

4

Reactant 2

HCID 708169831-(2,3-dichlorophenyl)-5-iodo-3-(trifluoromethyl)-1H-pyrazoleHCID 178418546HCID 178418546, compound

Product 1

HCID 708161751-(2,3-dichlorophenyl)-3-(trifluoromethyl)-1H-pyrazole-5-carbonitrileYield 59.5%

Reagents, catalysts & solvents 1

HCID 13387N-methyl-2-pyrrolidoneSolvent

Conditions

Temperature
200 °C

Procedure

To a stirred solution of 1-(2,3-dichlorophenyl)-5-iodo-3-(trifluoromethyl)-1H-pyrazole (11.1 g, 27.58 mmol, 1.0 eq) in NMP (50 mL) was added CuCN (2.39 g, 27.58 mmol, 1.0 eq.) and heated to 200° C. for 2 h. The reaction mixture was passed through a celite pad and washed with excess of ethyl acetate. The filtrate was washed with water and the ethyl acetate layer was separated, dried (Na2SO4), and the solvent evaporated. The resulting residue was purified by CC using ethyl acetate/PE (1:9) to get 1-(2,3-dichlorophenyl)-3-(trifluoromethyl)-1H-pyrazole-5-carbonitrile (5.02 g, crude, yellow solid).

Workup

  1. washwashed with excess of ethyl acetate
  2. washThe filtrate was washed with water
  3. customthe ethyl acetate layer was separated
  4. dry with materialdried (Na2SO4)
  5. customthe solvent evaporated
  6. customThe resulting residue was purified by CC

Sources & evidence

ORD record
ord-a94901afccc743b4968379255fbcfedf
Source dataset
uspto-grants-2015_02
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08946204B2

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes