Dichloromethane → 3-(3-Fluoro-5-chloro-2-pyridyl)-4-nitro-5-difluoromethoxy-1-methyl-[1H]-pyrazole

HRID 1532580Notes

Reaction equation

HRID 1532580 reaction equation
[F:1][C:2]1[C:3]([C:9]2[CH:13]=[C:12]([O:14][CH:15]([F:17])[F:16])[N:11]([CH3:18])[N:10]=2)=[N:4][CH:5]=[C:6]([Cl:8])[CH:7]=1.C(Cl)Cl.F[B-](F)(F)F.[O:27]=[N+:28]=[O:29]>C(OCC)(=O)C>[F:1][C:2]1[C:3]([C:9]2[C:13]([N+:28]([O-:29])=[O:27])=[C:12]([O:14][CH:15]([F:16])[F:17])[N:11]([CH3:18])[N:10]=2)=[N:4][CH:5]=[C:6]([Cl:8])[CH:7]=1

Participants

5

Reactant 3

HCID 6344DichloromethaneHCID 11073463Nitronium tetrafluoroborateHCID 217121323-(3-fluoro-5chloro-2-pyridyl)-5-difluoromethoxy-1-methyl-[1H]-pyrazole

Product 1

HCID 220135653-(3-Fluoro-5-chloro-2-pyridyl)-4-nitro-5-difluoromethoxy-1-methyl-[1H]-pyrazoleYield 93.6%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

4.0 g of 3-(3-fluoro-5chloro-2-pyridyl)-5-difluoromethoxy-1-methyl-[1H]-pyrazole (Example HIS) are initially introduced into 30 ml of methylene chloride. 3.83 g of nitronium tetrafluoroborate are added, while stirring and cooling in an ice-bath, and the mixture is subsequently stirred overnight at 22° C. The following day, it is poured onto water, and ethyl acetate is added. After extraction by shaking and separation of the phases, the organic phase is washed with dilute bicarbonate solution and brine, dried over sodium sulfate, filtered and concentrated in vacuo. 4.35 g of the desired title compound are obtained as a brown solid of melting point 108-109° C.

Workup

  1. temperaturecooling in an ice-bath
  2. additionis added
  3. extractionAfter extraction
  4. stirringby shaking
  5. customseparation of the phases
  6. washthe organic phase is washed with dilute bicarbonate solution and brine
  7. dry with materialdried over sodium sulfate
  8. filtrationfiltered
  9. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-17a14f1eaf404902a977619b10888c5c
Source dataset
uspto-grants-2001_03
Patent number
US06204221B1

Reaction notes

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