Sodium Hydroxide → ethyl 4-bromo-5-ethyl-1H-pyrrole-2-carboxylate

HRID 2233813Notes

Reaction equation

HRID 2233813 reaction equation
[Br:1]N1C(=O)CCC1=O.[CH2:9]([C:11]1[NH:15][C:14]([C:16]([O:18][CH2:19][CH3:20])=[O:17])=[CH:13][CH:12]=1)[CH3:10].[OH-].[Na+]>C(Cl)Cl>[Br:1][C:12]1[CH:13]=[C:14]([C:16]([O:18][CH2:19][CH3:20])=[O:17])[NH:15][C:11]=1[CH2:9][CH3:10]

Participants

5

Reactant 3

HCID 14798Sodium HydroxideHCID 67184N-bromobutanimideHCID 597485Ethyl 5-ethyl-1H-pyrrole-2-carboxylate2×

Product 1

HCID 68580112ethyl 4-bromo-5-ethyl-1H-pyrrole-2-carboxylateYield 68%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

N-Bromosuccinimide (5.86 g, 0.033 mol) was added to a solution of ethyl 5-ethyl-1H-pyrrole-2-carboxylate (Intermediate 12, 5.0 g, 0.03 mol) in DCM (85 ml) at 0° C., and the reaction was stirred for 30 minutes then poured to a chilled beaker containing 2 N NaOH (50 ml). The layers were separated and the aqueous layer was extracted with DCM (×3). The combined organic extracts were washed with water and brine, dried over magnesium sulfate and concentrated. The resultant dark brown solid was purified by flash chromatography (hexanes/EtOAc, 10:1) to give the title product as a white solid (5.0 g, 68%).

Workup

  1. additionthen poured to a chilled beaker
  2. customThe layers were separated
  3. extractionthe aqueous layer was extracted with DCM (×3)
  4. washThe combined organic extracts were washed with water and brine
  5. dry with materialdried over magnesium sulfate
  6. concentrationconcentrated
  7. customThe resultant dark brown solid was purified by flash chromatography (hexanes/EtOAc, 10:1)

Sources & evidence

ORD record
ord-e135598ffb5446758f60c3f60b9e7749
Source dataset
uspto-grants-2010_05
Patent number
US07709503B2

Reaction notes

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