Ethyl 5-bromo-4-(p-chlorophenyl)pyrrole-3-carboxylate → 5-Bromo-4-(p-chlorophenyl)pyrrole-3-carboxylic acid

HRID 1651699Notes

Reaction equation

HRID 1651699 reaction equation
[Br:1][C:2]1[NH:6][CH:5]=[C:4]([C:7]([O:9]CC)=[O:8])[C:3]=1[C:12]1[CH:17]=[CH:16][C:15]([Cl:18])=[CH:14][CH:13]=1>[OH-].[Na+]>[Br:1][C:2]1[NH:6][CH:5]=[C:4]([C:7]([OH:9])=[O:8])[C:3]=1[C:12]1[CH:17]=[CH:16][C:15]([Cl:18])=[CH:14][CH:13]=1

Participants

3

Reactant 1

HCID 15010185Ethyl 5-bromo-4-(p-chlorophenyl)pyrrole-3-carboxylate

Product 1

HCID 157530185-Bromo-4-(p-chlorophenyl)pyrrole-3-carboxylic acid

Reagents, catalysts & solvents 1

HCID 14798Sodium HydroxideSolvent

Procedure

Ethyl 5-bromo-4-(p-chlorophenyl)pyrrole-3-carboxylate (15 g., 0.045 mmol) is added to 200 mL of 10% sodium hydroxide and the slurry heated to reflux. After everything appears to dissolve the mixture is refluxed an additional 40 minutes. The mixture is cooled, filtered and the filtrate acidified. The white precipitate (8.0 g, 58%) is collected and dried. The solid has m.p. >205° C. and an NMR (d6 -DMSO) which showed a pyrrole proton at 7.52 (d). The mass spectrum is also consistent for a monobrominated compound.

Workup

  1. temperaturethe slurry heated to reflux
  2. dissolutionto dissolve the mixture
  3. temperatureis refluxed an additional 40 minutes
  4. temperatureThe mixture is cooled
  5. filtrationfiltered
  6. customThe white precipitate (8.0 g, 58%) is collected
  7. customdried

Sources & evidence

ORD record
ord-5ea6f256c41a4fb8b03160d44716d72a
Source dataset
uspto-grants-1990_05
Patent number
US04929634

Reaction notes

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