Potassium Carbonate → Methyl 4-bromo-2-(p-chlorophenyl)-1-(ethoxymethyl)-5-(trifluoromethyl)pyrrole-3-carboxylate
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]Participants
5
Reactant 3
Product 1
Reagents, catalysts & solvents 1
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
- stirringstirred for 1 hour
- stirringstirred for 3 hours
- extractionextracted with diethyl ether
- washThe combined organic extracts are washed with water
- dry with materialdried over anhydrous MgSO4
- concentrationconcentrated in vacuo
Sources & evidence
- ORD record
- ord-5e776dd183ef4da9a3a35c8db2901365
- Source dataset
- uspto-grants-1994_02
- Patent number
- US05286742
Reaction notes
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