Hydrochloric Acid → 1-(2-Fluoro-4-chloro-5-hydroxyphenyl)-3,5-dimethyl-4-nitropyrazole

HRID 580256Notes

Reaction equation

HRID 580256 reaction equation
[F:1][C:2]1[CH:7]=[C:6]([Cl:8])[C:5]([O:9]S(C)(=O)=O)=[CH:4][C:3]=1[N:14]1[C:18]([CH3:19])=[C:17]([N+:20]([O-:22])=[O:21])[C:16]([CH3:23])=[N:15]1.[OH-].[Na+].Cl>C(O)C>[F:1][C:2]1[CH:7]=[C:6]([Cl:8])[C:5]([OH:9])=[CH:4][C:3]=1[N:14]1[C:18]([CH3:19])=[C:17]([N+:20]([O-:22])=[O:21])[C:16]([CH3:23])=[N:15]1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 142557491-(2-Fluoro-4-chloro-5-methylsulfonyloxyphenyl)-3,5-dimethyl-4-nitropyrazole

Product 1

HCID 139211811-(2-Fluoro-4-chloro-5-hydroxyphenyl)-3,5-dimethyl-4-nitropyrazoleYield 98%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
40 °C

Procedure

A mixture of 1-(2-fluoro-4-chloro-5-methylsulfonyloxyphenyl)-3,5-dimethyl-4-nitropyrazole (36.5 g), 2N aqueous sodium hydroxide solution (100 ml) and ethanol (50 ml) was stirred at 40° C. for 30 minutes. After cooling, the reaction mixture was acidified with an aqueous hydrochloric acid solution and extracted with toluene. The toluene layer thus obtained was washed with water and dried over anhydrous sodium sulfate. Removal of the solvent by distillation in vacuo gave the titled compound (28.1 g) as a pale yellow crystalline solid. Recrystallization of this solid from a mixture of n-hexane and ethyl acetate afforded a white crystalline solid. m.p. 157°-158° C.

Workup

  1. temperatureAfter cooling
  2. extractionextracted with toluene
  3. customThe toluene layer thus obtained
  4. washwas washed with water
  5. dry with materialdried over anhydrous sodium sulfate
  6. customRemoval of the solvent
  7. distillationby distillation in vacuo

Sources & evidence

ORD record
ord-194b7c88cc934d0981a4d2b2225ff8da
Source dataset
uspto-grants-1988_06
Patent number
US04752326

Reaction notes

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