Water → 1-Methyl-5-difluoromethoxy-4-chloro-3-(2-fluoro-4-chlorophenyl)pyrazole

HRID 634561Notes

Reaction equation

HRID 634561 reaction equation
[CH3:1][N:2]1[C:6]([O:7][CH:8]([F:10])[F:9])=[CH:5][C:4]([C:11]2[CH:16]=[CH:15][C:14]([Cl:17])=[CH:13][C:12]=2[F:18])=[N:3]1.[Cl:19]N1C(=O)CCC1=O.O>CN(C)C=O>[CH3:1][N:2]1[C:6]([O:7][CH:8]([F:9])[F:10])=[C:5]([Cl:19])[C:4]([C:11]2[CH:16]=[CH:15][C:14]([Cl:17])=[CH:13][C:12]=2[F:18])=[N:3]1

Participants

5

Reactant 3

HCID 962WaterHCID 31398ChlorosuccinimideHCID 11357876HCID 11357876, compound

Product 1

HCID 114383281-Methyl-5-difluoromethoxy-4-chloro-3-(2-fluoro-4-chlorophenyl)pyrazoleYield 98.1%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A solution of 16.2 grams (0.059 mole) of 1-methyl-5-difluoromethoxy-3-(2-fluoro-4-chlorophenyl)pyrazole and 8.5 grams (0.064 mole) of N-chlorosuc-cinimide in about 500 mL of N,N-dimethylformamide was stirred at ambient temperature for about 18 hours. After this time the reaction mixture was poured into about 1600 mL of water and then extracted with two portions of diethyl ether. The combined extracts were washed with one portion of aqueous 10% lithium chloride and two portions of a saturated aqueous solution of sodium chloride. The organic layer was dried with magnesium sulfate and filtered. The filtrate was concentrated under reduced pressure, yielding 18.0 grams of 1-methyl-5-difluoromethoxy-4-chloro-3-(2-fluoro-4-chlorophenyl)pyrazole. The NMR spectrum was consistent with the proposed structure.

Workup

  1. extractionextracted with two portions of diethyl ether
  2. washThe combined extracts were washed with one portion of aqueous 10% lithium chloride and two portions of a saturated aqueous solution of sodium chloride
  3. dry with materialThe organic layer was dried with magnesium sulfate
  4. filtrationfiltered
  5. concentrationThe filtrate was concentrated under reduced pressure

Sources & evidence

ORD record
ord-0d9fe556128a4b0b8708ed7d0d406e3c
Source dataset
uspto-grants-2001_02
Patent number
USH0001942H1

Reaction notes

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