Potassium Hydroxide → 4-Bromo-2-(p-chlorophenyl)-1-(ethoxymethyl)-5-(trifluoromethyl)pyrrole-3-carboxylic acid

HRID 274742Notes

Reaction equation

HRID 274742 reaction equation
[Br:1][C:2]1[C:3]([C:22]([O:24]C)=[O:23])=[C:4]([C:15]2[CH:20]=[CH:19][C:18]([Cl:21])=[CH:17][CH:16]=2)[N:5]([CH2:11][O:12][CH2:13][CH3:14])[C:6]=1[C:7]([F:10])([F:9])[F:8].[OH-].[K+]>O>[Br:1][C:2]1[C:3]([C:22]([OH:24])=[O:23])=[C:4]([C:15]2[CH:20]=[CH:19][C:18]([Cl:21])=[CH:17][CH:16]=2)[N:5]([CH2:11][O:12][CH2:13][CH3:14])[C:6]=1[C:7]([F:8])([F:10])[F:9]

Participants

4

Reactant 2

HCID 14797Potassium HydroxideHCID 20093625Methyl 4-bromo-2-(p-chlorophenyl)-1-(ethoxymethyl)-5-(trifluoromethyl)pyrrole-3-carboxylate

Product 1

HCID 200936204-Bromo-2-(p-chlorophenyl)-1-(ethoxymethyl)-5-(trifluoromethyl)pyrrole-3-carboxylic acidYield 50.9%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A mixture of methyl 4-bromo-2-(p-chlorophenyl)-1-(ethoxymethyl)-5-(trifluoromethyl)pyrrole-3-carboxylate (13.1 g) and potassium hydroxide (3.12 g, 85%, 48 mmol) is stirred at room temperature for 20 hours, stirred at reflux for 2 hours, diluted with water, washed with diethyl ether, acidified to pH 4 with 1N hydrochloric acid and filtered to obtain a solid. The solid is washed with water and petroleum ether and dried to give the title product as a white solid (6.45 g) which is identified by 1H NMR spectral analysis.

Workup

  1. stirringstirred
  2. temperatureat reflux for 2 hours
  3. washwashed with diethyl ether
  4. filtrationfiltered
  5. customto obtain a solid
  6. washThe solid is washed with water and petroleum ether
  7. customdried

Sources & evidence

ORD record
ord-3f81f6c7abbd460f9299844f56ca6f96
Source dataset
uspto-grants-1995_02
Patent number
US05389669

Reaction notes

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