Hydrochloric Acid → 5-bromo-3-(trifluoromethyl)-1H-pyrazole-1-acetic acid

HRID 2096017Notes

Reaction equation

HRID 2096017 reaction equation
[Br: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>[Br: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

5

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 68745175ethyl 5-bromo-3-(trifluoromethyl)-1H-pyrazole-1-acetate2×

Product 1

HCID 687457105-bromo-3-(trifluoromethyl)-1H-pyrazole-1-acetic acid

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A solution of ethyl 5-bromo-3-(trifluoromethyl)-1H-pyrazole-1-acetate (i.e. the product of Example 11, Step C) (2.84 g, 9.4 mmol) in tetrahydrofuran (10 mL) was treated with a 50 wt. % aqueous sodium hydroxide solution (1.0 mL). The reaction mixture was stirred at room temperature for 2 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 2.26 g of the title compound as a light brown solid. Recrystallization from 1-chlorobutane (20 mL) gave 0.68 g of the title compound as lustrous light pink plates.

Workup

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

Sources & evidence

ORD record
ord-def839b38aa0485ebae9f347b34082a4
Source dataset
uspto-grants-2013_05
Patent number
US08449898B2

Reaction notes

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