Hydrochloric Acid → 2-(5-chloro-3-(trifluoromethyl)-1H-pyrazol-1-yl)acetic acid

HRID 238677Notes

Reaction equation

HRID 238677 reaction equation
[Cl:1][C:2]1[N:6]([CH2:7][C:8]([O:10]CC)=[O:9])[N:5]=[C:4]([C:13]([F:16])([F:15])[F:14])[CH:3]=1.[OH-].[Na+].Cl>O1CCCC1.O>[Cl:1][C:2]1[N:6]([CH2:7][C:8]([OH:10])=[O:9])[N:5]=[C:4]([C:13]([F:16])([F:14])[F:15])[CH:3]=1

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 66016896ethyl 5-chloro-3-(trifluoromethyl)-1H-pyrazole-1-acetate2×

Product 1

HCID 660151092-(5-chloro-3-(trifluoromethyl)-1H-pyrazol-1-yl)acetic acid

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

A solution of ethyl 5-chloro-3-(trifluoromethyl)-1H-pyrazole-1-acetate (i.e. the product of Example 10, Step D or D1) (218 mg, 0.85 mmol) in tetrahydrofuran (1 mL) was treated with a 50 wt. % aqueous solution of sodium hydroxide (0.2 mL) in water (0.6 mL). The reaction mixture was stirred at room temperature for 4 h. The reaction mixture was treated with concentrated aqueous hydrochloric acid to lower the pH to 1, and then extracted with ethyl acetate. The extract was dried (MgSO4) and concentrated under pressure to give 140 mg of the title compound. This compound was of sufficient purity to use in subsequent reactions.

Workup

  1. extractionextracted with ethyl acetate
  2. dry with materialThe extract was dried (MgSO4)
  3. concentrationconcentrated under pressure

Sources & evidence

ORD record
ord-94fcd7f2a487475fa0e436b5f3332747
Source dataset
uspto-grants-2014_02
Patent number
US08642634B2

Reaction notes

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