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

HRID 377650Notes

Reaction equation

HRID 377650 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].[CH:21]([Sn](CCCC)(CCCC)CCCC)=[CH2:22].O.CCOCC>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:21]=[CH2:22])=[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

7

Reactant 4

HCID 962WaterHCID 3283Diethyl EtherHCID 81998TributylvinyltinHCID 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 vinyltri-n-butyltin (116 ml) and tetrakis(triphenylphosphine)palladium(0) (3.5 g,) was stirred at 75° C. for 3 hours. The reaction mixture was poured into water (600 ml) and ether (600 ml). The organic layer was separated, washed with water (×5), brine (700 ml), dried (Na2SO4) and evaporated. The residue was recrystallised from propan-2-ol to give the title compound as a pale brown solid, m.p.75-6° C.

Workup

  1. customThe organic layer was separated
  2. washwashed with water (×5), brine (700 ml)
  3. dry with materialdried (Na2SO4)
  4. customevaporated
  5. customThe residue was recrystallised from propan-2-ol

Sources & evidence

ORD record
ord-3ee4f0aa37da47a4892c306d1638fef8
Source dataset
uspto-grants-2000_02
Patent number
US06028096

Reaction notes

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