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Potassium Carbonate → Methyl 4-bromo-2-(p-chlorophenyl)-1-(ethoxymethyl)-5-(trifluoromethyl)pyrrole-3-carboxylate

HRID 1975400
Notes
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Reaction equation

HRID 1975400 reaction equation
[Br:1][C:2]1[C:3]([C:18]([O:20][CH3:21])=[O:19])=[C:4]([C:11]2[CH:16]=[CH:15][C:14]([Cl:17])=[CH:13][CH:12]=2)[NH:5][C:6]=1[C:7]([F:10])([F:9])[F:8].C(=O)([O-])[O-].[K+].[K+].[CH2:28]([O:30][CH2:31]Cl)[CH3:29]>O>[Br:1][C:2]1[C:3]([C:18]([O:20][CH3:21])=[O:19])=[C:4]([C:11]2[CH:12]=[CH:13][C:14]([Cl:17])=[CH:15][CH:16]=2)[N:5]([CH2:31][O:30][CH2:28][CH3:29])[C:6]=1[C:7]([F:10])([F:9])[F:8]
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 3

HCID 11430Potassium Carbonate3×HCID 18523Chloromethyl ethyl ether3×HCID 20093623Methyl 4-bromo-2-(p-chlorophenyl)-5-(trifluoromethyl)pyrrole-3-carboxylate

Product 1

HCID 20093625Methyl 4-bromo-2-(p-chlorophenyl)-1-(ethoxymethyl)-5-(trifluoromethyl)pyrrole-3-carboxylateYield 123.4%

Reagents, catalysts & solvents 1

HCID 962
Water
Solvent

Procedure

A mixture of methyl 4-bromo-2-(p-chlorophenyl)-5-(trifluoromethyl)pyrrole-3-carboxylate (9.2 g, 24.1 mmol), potassium carbonate (4.96 g, 36 mmol) and chloromethyl ethyl ether (3.3 mL, 36 mmol) is stirred at room temperature for 21 hours, treated with potassium carbonate (4.9 g) and chloromethyl ethyl ether (3.3 mL), stirred for 1 hour, treated with potassium carbonate (4.9 g) and chloromethyl ethyl ether (3.3 mL) stirred for 3 hours, diluted with water and extracted with diethyl ether. The combined organic extracts are washed with water, dried over anhydrous MgSO4 and concentrated in vacuo to obtain the title product as a brown oil (13.1 g) which is used in the next step without further purification.

Workup

  1. stirringstirred for 1 hour
  2. stirringstirred for 3 hours
  3. extractionextracted with diethyl ether
  4. washThe combined organic extracts are washed with water
  5. dry with materialdried over anhydrous MgSO4
  6. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-5e776dd183ef4da9a3a35c8db2901365
Source dataset
uspto-grants-1994_02
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US05286742

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes