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

HRID 1528546
Notes
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Reaction equation

HRID 1528546 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
ParticipantsProcedureWorkupSources & evidenceReaction notes

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 solution of 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-cd09bebdf9af4df59f5fbd239d1dc1f0
Source dataset
uspto-grants-2015_07
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US09090604B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes