Hydrochloric Acid → 5-(4-Chloro-5-difluoromethoxy-1-methyl-1H-pyrazol-3-yl)-2,4-dichlorobenzoic acid

HRID 1870093Notes

Reaction equation

HRID 1870093 reaction equation
O.O.P([O-])(O)(O)=O.[Na+].[Cl:9][C:10]1[C:11]([C:20]2[C:21]([Cl:29])=[CH:22][C:23]([Cl:28])=[C:24]([CH:27]=2)[CH:25]=[O:26])=[N:12][N:13]([CH3:19])[C:14]=1[O:15][CH:16]([F:18])[F:17].OO.Cl([O-])=[O:33].[Na+].Cl>O.C(#N)C>[Cl:9][C:10]1[C:11]([C:20]2[C:21]([Cl:29])=[CH:22][C:23]([Cl:28])=[C:24]([CH:27]=2)[C:25]([OH:33])=[O:26])=[N:12][N:13]([CH3:19])[C:14]=1[O:15][CH:16]([F:17])[F:18]

Participants

8

Reactant 5

HCID 313Hydrochloric AcidHCID 784Hydrogen PeroxideHCID 156721724-Chloro-3-(2,4-dichloro-5-formylphenyl)-5-difluoromethoxy-1-methyl-1H-pyrazoleHCID 23668197Sodium ChloriteHCID 23673460Sodium Phosphate, Monobasic, Dihydrate

Product 1

HCID 150305955-(4-Chloro-5-difluoromethoxy-1-methyl-1H-pyrazol-3-yl)-2,4-dichlorobenzoic acid

Reagents, catalysts & solvents 2

HCID 962WaterSolvent2×HCID 6342AcetonitrileSolvent

Procedure

A solution of 2.5 g (16 mmol) of sodium dihydrogen phosphate dihydrate in 25 ml of water was added dropwise at 10-15° C. to a solution of 21.3 g (60 mmol) of 5-(4-chloro-5-difluoromethoxy-1-methyl-1H-pyrazol-3-yl)-2,4-dichlorobenzaldehyde in 120 ml of acetonitrile. 6 ml of a 30% by weight hydrogen peroxide solution and then, in the course of two hours, a solution of 8.7 g (96 mmol) of sodium chlorite in 80 ml of water were added dropwise to this mixture. The reaction mixture was stirred for a further hour and then acidified with 3 N hydrochloric acid. The solids content was separated from the resulting suspension and dried. Yield: 13.7 g; m.p. 159-160° C.

Workup

  1. customThe solids content was separated from the resulting suspension
  2. customdried

Sources & evidence

ORD record
ord-aa2b7fcc5ad54bc283f4acb4f773ae5e
Source dataset
uspto-grants-2000_08
Patent number
US06096689

Reaction notes

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