Water → 3-Cyano-1-(2,6-dichloro-4-trifluoromethylphenyl)-4-ethenylpyrazole

HRID 1383587Notes

Reaction equation

HRID 1383587 reaction equation
[C:1]([C:3]1[C:7](I)=[CH:6][N:5]([C:9]2[C:14]([Cl:15])=[CH:13][C:12]([C:16]([F:19])([F:18])[F:17])=[CH:11][C:10]=2[Cl:20])[N:4]=1)#[N:2].O.[CH3:22][CH2:23]OCC>CN(C)C=O.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[C:1]([C:3]1[C:7]([CH:22]=[CH2:23])=[CH:6][N:5]([C:9]2[C:14]([Cl:15])=[CH:13][C:12]([C:16]([F:19])([F:18])[F:17])=[CH:11][C:10]=2[Cl:20])[N:4]=1)#[N:2]

Participants

6

Reactant 3

HCID 962WaterHCID 3283Diethyl EtherHCID 211881263-Cyano-1-(2,6-dichloro-4-trifluoromethylphenyl)-4-iodopyrazole

Product 1

HCID 211880943-Cyano-1-(2,6-dichloro-4-trifluoromethylphenyl)-4-ethenylpyrazole

Reagents, catalysts & solvents 2

HCID 178418397HCID 178418397, compoundCatalystHCID 6228DimethylformamideSolvent

Conditions

Temperature
75 °C

Procedure

A solution of 3-cyano-1-(2,6-dichloro-4-trifluoromethylphenyl)4-iodopyrazole (58 g) in dimethylformamide (350 ml) containing yinyltri-n-butyltin (116 ml) and tetrakis(triphenylphosphine)palladium(0) (3.5 g) was stirred at 75° C. for 3 hours. The reaction nixture was poured into water (600 ml) and ether (600 ml). The organic layer was washed with water (5 times), brine (700 ml) and dried over sodium sulphate. Removal of the solvent in vacuo was followed by recrystallisation of the residue from propan-2-ol, to give the title compound as a pale brown solid, m.p. 75-6° C.

Workup

  1. washThe organic layer was washed with water (5 times), brine (700 ml)
  2. dry with materialdried over sodium sulphate
  3. customRemoval of the solvent in vacuo
  4. customwas followed by recrystallisation of the residue from propan-2-ol

Sources & evidence

ORD record
ord-443db0514f744d91a7ccceca9b731776
Source dataset
uspto-grants-2001_07
Patent number
US06255333B1

Reaction notes

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