Cyclopropanecarbonyl chloride → 3-Cyano-4-cyclopropylcarbonyl-1-(2,6-dichloro-4-trifluoromethylphenyl)pyrazole

HRID 377653Notes

Reaction equation

HRID 377653 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].C([Li])CCC.[CH:26]1([C:29](Cl)=[O:30])[CH2:28][CH2:27]1.C(=O)([O-])O.[Na+]>O1CCCC1>[C:1]([C:3]1[C:7]([C:29]([CH:26]2[CH2:28][CH2:27]2)=[O:30])=[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 4

HCID 77637Cyclopropanecarbonyl chlorideHCID 516892Sodium BicarbonateHCID 211881263-Cyano-1-(2,6-dichloro-4-trifluoromethylphenyl)-4-iodopyrazoleHCID 178418339Butyllithium

Product 1

HCID 193564833-Cyano-4-cyclopropylcarbonyl-1-(2,6-dichloro-4-trifluoromethylphenyl)pyrazole

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a stirred solution of 3-cyano-1-(2,6-dichloro-4-trifluoromethylphenyl)-4-iodopyrazole (0.22 g) in tetrahydrofuran (5 ml) at -78° C. under an atmosphere of nitrogen was added, at such a rate that the temperature of the reaction mixture did not exceed -65° C., n-butyllithium (0.21 ml of a 2.5M solution in hexanes). After stirring for a further 5 minutes cyclopropanecarbonyl chloride (0.13 ml) was added and the mixture allowed to warm to room temperature. The reaction mixture was poured into saturated aqueous sodium hydrogen carbonate solution (5 ml) and extracted twice with ether (25 ml). The combined organic layers were washed with water (50 ml), dried (Na2SO4) and evaporated to give a brown oil which was purified by column chromatography on silica gel (40 g) eluted with dichloromethane. Combination and evaporation of suitable fractions gave the title compound as a white solid, m.p. 195-197° C.

Workup

  1. customdid not exceed -65° C.
  2. additionwas added
  3. extractionextracted twice with ether (25 ml)
  4. washThe combined organic layers were washed with water (50 ml)
  5. dry with materialdried (Na2SO4)
  6. customevaporated
  7. customto give a brown oil which
  8. customwas purified by column chromatography on silica gel (40 g)
  9. washeluted with dichloromethane
  10. customCombination and evaporation of suitable fractions

Sources & evidence

ORD record
ord-796df4d72e2240468c71a6db5d8ceafe
Source dataset
uspto-grants-2000_02
Patent number
US06028096

Reaction notes

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