Sodium Hydroxide → HCID 13370522, compound

HRID 2412928Notes

Reaction equation

HRID 2412928 reaction equation
[CH3:1][N:2]1[C:6]([C:7]([O:9]C)=[O:8])=[C:5]([Br:11])[C:4]([C:12]2[CH:17]=[CH:16][CH:15]=[C:14]([C:18]([F:21])([F:20])[F:19])[CH:13]=2)=[N:3]1.[OH-].[Na+]>C(O)C>[CH3:1][N:2]1[C:6]([C:7]([OH:9])=[O:8])=[C:5]([Br:11])[C:4]([C:12]2[CH:17]=[CH:16][CH:15]=[C:14]([C:18]([F:21])([F:19])[F:20])[CH:13]=2)=[N:3]1

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 20431381HCID 20431381, compound

Product 1

HCID 13370522HCID 13370522, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

Following the above procedure, the same methyl ester was brominated in refluxing acetic acid. Methyl 1-methyl-3-(3-trifluoromethylphenyl)-4-bromopyrazole-5-carboxylate thus formed was purified by chromatography over silica gel using methylene dichloride as the eluant. 3.0 g. of 1-methyl-3-(3-trifluoromethylphenyl)-4-bromopyrazole-5-carboxylic acid were obtained (from 8.0 g. of unbrominated ester starting material). The ester was hydrolyzed by the procedure of Example 1 using dilute aqueous sodium hydroxide in aqueous ethanol and the free acid isolated by acidification of the hydrolysis mixture. Recrystallization of the free acid ethanol yielded 1-methyl-3-(3-trifluoromethylphenyl)-4-bromopyrazole-5-carboxylic acid melting at 182°-4° C.

Workup

  1. customthe free acid isolated by acidification of the hydrolysis mixture
  2. customRecrystallization of the free acid ethanol

Sources & evidence

ORD record
ord-0f548efa54be40cdb4d6ecdf89b610cb
Source dataset
uspto-grants-1985_01
Patent number
US04495195

Reaction notes

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