Isopropyltriphenylphosphonium iodide → 3-Cyano-1-(2,6-dichloro-4-trifluoromethylphenyl)-4-(2-methylprop-1-enyl)pyrazole

HRID 1383600Notes

Reaction equation

HRID 1383600 reaction equation
[I-].[CH:2]([P+](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)([CH3:4])[CH3:3].C([Li])CCC.[C:29]([C:31]1[C:35]([CH:36]=O)=[CH:34][N:33]([C:38]2[C:43]([Cl:44])=[CH:42][C:41]([C:45]([F:48])([F:47])[F:46])=[CH:40][C:39]=2[Cl:49])[N:32]=1)#[N:30]>CCOCC>[C:29]([C:31]1[C:35]([CH:36]=[C:2]([CH3:4])[CH3:3])=[CH:34][N:33]([C:38]2[C:43]([Cl:44])=[CH:42][C:41]([C:45]([F:48])([F:47])[F:46])=[CH:40][C:39]=2[Cl:49])[N:32]=1)#[N:30]

Participants

5

Reactant 3

HCID 2723783Isopropyltriphenylphosphonium iodideHCID 184179813-Cyano-1-(2,6-dichloro-4-trifluoromethylphenyl)4-formylpyrazoleHCID 178418339Butyllithium

Product 1

HCID 211881073-Cyano-1-(2,6-dichloro-4-trifluoromethylphenyl)-4-(2-methylprop-1-enyl)pyrazole

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent2×

Procedure

Isopropyltriphenylphosphonium iodide (0.97 g) in anhydrous ether (10 ml) was treated at room temperature with n-butyllithium (0.9 ml of a 2.5M solution in hexanes). To the resulting dark red solution was added 3-cyano-1-(2,6-dichloro-4-trifluoromethylphenyl)4-formylpyrazole (0.6 g) in ether (20 ml) and the mixture stirred for 2 hours. The solution was washed with water (20 ml) and the separated organic layer dried (MgSO4) and evaporated. The residue was purified by column chromatography on silica gel eluted with dichloromethane. Combination and evaporation of suitable fractions provided the title compound as a pale tan solid m.p. 72-74° C.

Workup

  1. washThe solution was washed with water (20 ml)
  2. dry with materialthe separated organic layer dried (MgSO4)
  3. customevaporated
  4. customThe residue was purified by column chromatography on silica gel
  5. washeluted with dichloromethane
  6. customCombination and evaporation of suitable fractions

Sources & evidence

ORD record
ord-bf108a26307e41fbae8e4500f4e7efba
Source dataset
uspto-grants-2001_07
Patent number
US06255333B1

Reaction notes

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