Bromine → Methyl 4-bromo-2-(p-chlorophenyl)-5-(trifluoromethyl)pyrrole-3-carboxylate

HRID 1975399Notes

Reaction equation

HRID 1975399 reaction equation
[Br:1]Br.[Cl:3][C:4]1[CH:9]=[CH:8][C:7]([C:10]2[NH:11][C:12]([C:19]([F:22])([F:21])[F:20])=[CH:13][C:14]=2[C:15]([O:17][CH3:18])=[O:16])=[CH:6][CH:5]=1.C([O-])(=O)C.[Na+]>C(O)(=O)C.S([O-])([O-])=O.[Na+].[Na+]>[Br:1][C:13]1[C:14]([C:15]([O:17][CH3:18])=[O:16])=[C:10]([C:7]2[CH:6]=[CH:5][C:4]([Cl:3])=[CH:9][CH:8]=2)[NH:11][C:12]=1[C:19]([F:22])([F:20])[F:21]

Participants

6

Reactant 3

HCID 24408BromineHCID 517045Sodium AcetateHCID 11034029Methyl 2-(p-chlorophenyl)-5-(trifluoromethyl)pyrrole-3-carboxylate

Product 1

HCID 20093623Methyl 4-bromo-2-(p-chlorophenyl)-5-(trifluoromethyl)pyrrole-3-carboxylateYield 82.4%

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 24437Sodium SulfiteSolvent

Procedure

Bromine (2.3 mL, 43.7 mmol) is added to a solution of methyl 2-(p-chlorophenyl)-5-(trifluoromethyl)pyrrole-3-carboxylate (8.44 g, 29.2 mmol) and sodium acetate (3.6 g, 43.7 mmol) in acetic acid. The reaction mixture is stirred for 30 minutes, diluted with a 0.4 wt/wt % sodium sulfite solution and extracted with diethyl ether. The organic extracts are combined, washed with saturated sodium hydrogen carbonate solution, dried over anhydrous Na2SO4 and concentrated in vacuo to obtain an oil which solidifies to give the title product as a solid (9.2 g) which is identified by 1H and 13C NMR spectral analyses.

Workup

  1. extractionextracted with diethyl ether
  2. washwashed with saturated sodium hydrogen carbonate solution
  3. dry with materialdried over anhydrous Na2SO4
  4. concentrationconcentrated in vacuo
  5. customto obtain an oil which

Sources & evidence

ORD record
ord-62b3986829604dc3b85efca49256bad5
Source dataset
uspto-grants-1994_02
Patent number
US05286742

Reaction notes

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