N-bromobutanimide → ethyl 5-bromo-1H-pyrrole-2-carboxylate

HRID 1178112Notes

Reaction equation

HRID 1178112 reaction equation
C1C(=O)N([Br:8])C(=O)C1.[CH2:9]([O:11][C:12]([C:14]1[NH:15][CH:16]=[CH:17][CH:18]=1)=[O:13])[CH3:10]>C1COCC1.CO>[CH2:9]([O:11][C:12]([C:14]1[NH:15][C:16]([Br:8])=[CH:17][CH:18]=1)=[O:13])[CH3:10]

Participants

4

Reactant 2

HCID 67184N-bromobutanimideHCID 255670Ethyl 1H-pyrrole-2-carboxylate

Product 1

HCID 59559613ethyl 5-bromo-1H-pyrrole-2-carboxylateYield 55.3%

Reagents, catalysts & solvents 1

HCID 21899815MeOH tetrahydrofuranSolvent

Procedure

NBS (0.15 mg, 0.83 mmol) was added to a stirred cold (0-5° C.) solution of 1H-pyrrole-2-carboxylic acid ethyl ester (200 mg, 1.44 mmol) in THF: MeOH (2:1, 24 mL). Stirring was continued at same temperature for 2 hrs. Solvent was removed under vacuum to get the residue. The residue obtained was purified by column chromatography (using silica gel of 200-430 mesh and 10% Ether in Hexane as eluent) to afford 100 mg (31.95% yield) of 5-bromo-1H-pyrrole-2-carboxylic acid ethyl ester. 1H NMR (CDCl3): δ 9.4 (bs, 1H), 6.8 (s, 1H), 6.2 (s, 1H), 4.4-4.2 (q, 2H), 1.4 (t, 3H).

Workup

  1. customSolvent was removed under vacuum
  2. customto get the residue
  3. customThe residue obtained
  4. customwas purified by column chromatography (using silica gel of 200-430 mesh and 10% Ether in Hexane as eluent)

Sources & evidence

ORD record
ord-abe87a9812ca4c07bb0cded088cc63b0
Source dataset
uspto-grants-2010_11
Patent number
US07842696B2

Reaction notes

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