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

HRID 1260084Notes

Reaction equation

HRID 1260084 reaction equation
COCCCC[N:7]1[CH:11]=[CH:10][CH:9]=[C:8]1[C:12]([O:14][CH3:15])=[O:13].[Br:16]N1C(=O)CCC1=O>ClCCl>[Br:16][C:11]1[NH:7][C:8]([C:12]([O:14][CH3:15])=[O:13])=[CH:9][CH:10]=1

Participants

4

Reactant 2

HCID 67184N-bromobutanimideHCID 59356613HCID 59356613, compound

Product 1

HCID 11600885Methyl 5-bromo-1H-pyrrole-2-carboxylateYield 50.6%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Methyl 1-(4-methoxybutyl)-1H-pyrrole-2-carboxylate (4.5 g) was dissolved in dichloromethane (30 ml), N-bromosuccinimide (4.0 g) was added and the mixture was stirred for 1 hr. The reaction mixture was washed successively with water and brine, and dried over anhydrous sodium sulfate. The solvent was evaporated under reduced pressure. The residue was subjected to silica gel column chromatography, and a fraction eluted with ethyl acetate-hexane (1:4) was concentrated under reduced pressure to give the object product (2.2 g).

Workup

  1. washThe reaction mixture was washed successively with water and brine
  2. dry with materialdried over anhydrous sodium sulfate
  3. customThe solvent was evaporated under reduced pressure
  4. washa fraction eluted with ethyl acetate-hexane (1:4)
  5. concentrationwas concentrated under reduced pressure

Sources & evidence

ORD record
ord-237a70aed8d440cda747cc04c8efd5ed
Source dataset
uspto-grants-2013_06
Patent number
US08466282B2

Reaction notes

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