N-bromobutanimide → Ethyl 5-bromo-4-methyl-1H-pyrrole-3-carboxylate

HRID 912582Notes

Reaction equation

HRID 912582 reaction equation
[CH3:1][C:2]1[C:3]([C:7]([O:9][CH2:10][CH3:11])=[O:8])=[CH:4][NH:5][CH:6]=1.C1C(=O)N([Br:19])C(=O)C1>C1COCC1>[Br:19][C:6]1[NH:5][CH:4]=[C:3]([C:7]([O:9][CH2:10][CH3:11])=[O:8])[C:2]=1[CH3:1]

Participants

4

Reactant 2

HCID 67184N-bromobutanimideHCID 235044Ethyl 4-methyl-1h-pyrrole-3-carboxylate

Product 1

HCID 66925114Ethyl 5-bromo-4-methyl-1H-pyrrole-3-carboxylateYield 86%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
-30 °C

Procedure

To a solution of ethyl 4-methyl-3-pyrrolecarboxylate (1.57 g, 10 mmol) in anhyd THF (30 mL) cooled to −78° C. was added NBS (1.9 g, 10 mmol). After stirring 1 h at −30° C., the reaction mixture was concentrated under reduced pressure. The residue was purified by column chromatography, eluting with EtOAc-Hex (0:100 to 30:70), to yield ethyl 5-bromo-4-methyl-1H-pyrrole-3-carboxylate (2.0, 86%) as a white solid. 1H-NMR (CDCl3): δ 8.54 (1H, brs), 7.38 (1H, d), 4.27 (2H, q), 2.24 (3H, s), 1.33 (3H, t).

Workup

  1. concentrationthe reaction mixture was concentrated under reduced pressure
  2. customThe residue was purified by column chromatography
  3. washeluting with EtOAc-Hex (0:100 to 30:70)

Sources & evidence

ORD record
ord-75654bcaff424a289fca944869786fe7
Source dataset
uspto-grants-2011_09
Patent number
US08026237B2

Reaction notes

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