N-bromobutanimide → Ethyl 5-bromo-4-(p-chlorophenyl)pyrrole-3-carboxylate

HRID 2209569Notes

Reaction equation

HRID 2209569 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[C:9]([C:13]([O:15][CH2:16][CH3:17])=[O:14])=[CH:10][NH:11][CH:12]=2)=[CH:4][CH:3]=1.[Br:18]N1C(=O)CCC1=O>O1CCCC1>[Br:18][C:12]1[NH:11][CH:10]=[C:9]([C:13]([O:15][CH2:16][CH3:17])=[O:14])[C:8]=1[C:5]1[CH:6]=[CH:7][C:2]([Cl:1])=[CH:3][CH:4]=1

Participants

4

Reactant 2

HCID 67184N-bromobutanimideHCID 470434ethyl 4-(4-chlorophenyl)-1H-pyrrole-3-carboxylate

Product 1

HCID 15010185Ethyl 5-bromo-4-(p-chlorophenyl)pyrrole-3-carboxylateYield 90,348.398%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Ethyl 4-(p-chlorophenyl)pyrrole-3-carboxylate (1.6 g., 0.0064 mmol) is dissolved in tetrahydrofuran (40 mL). N-bromosuccinimide (1.14 g., 0.0064 mmol) is added in small portions at 25°-28° C. After the addition is complete, the solution is stirred overnight at room temperature. The solution is concentrated in vacuo and the solid residue partioned between water and ether. The ether layer is separated and dried over magnesium sulfate. Work-up of the ether extract leaves 1.9 g (90%) Of a white solid which is purified by stirring with a mixture of 80/20 hexane/ethyl acetate. The insoluble solid (1.3 g, 62%) is collected and has m.p. 161°-164° C.

Workup

  1. additionAfter the addition
  2. concentrationThe solution is concentrated in vacuo
  3. customThe ether layer is separated
  4. dry with materialdried over magnesium sulfate
  5. extractionextract

Sources & evidence

ORD record
ord-273167738cbd4ca8b9290232994c9d95
Source dataset
uspto-grants-1995_10
Patent number
US05455263

Reaction notes

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