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

HRID 1842885Notes

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

Participants

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

washwashed with excess of ethyl acetate
washThe filtrate was washed with water
customthe ethyl acetate layer was separated
dry with materialdried (Na2SO4)
customthe solvent evaporated
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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