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

HRID 1359656Notes

Reaction equation

HRID 1359656 reaction equation
[CH3:1][N:2]1[CH:6]=[CH:5][CH:4]=[C:3]1[C:7]([O:9][CH3:10])=[O:8].[Br:11]N1C(=O)CCC1=O>C(Cl)Cl>[Br:11][C:6]1[N:2]([CH3:1])[C:3]([C:7]([O:9][CH3:10])=[O:8])=[CH:4][CH:5]=1

Participants

4

Reactant 2

HCID 67184N-bromobutanimideHCID 142178Methyl 1-methylpyrrole-2-carboxylate

Product 1

HCID 22350505Methyl 5-bromo-1-methyl-1H-pyrrole-2-carboxylateYield 64%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a dry flask is added methyl 1-methyl-1H-pyrrole-2-carboxylate (12.0 g, 86.4 mmol) and 150 mL of dry CH2Cl2, and the flask is wrapped in foil and purged with nitrogen. N-bromosuccinimide (16.2 g, 90.7 mmol) is added in one portion and the mixture is stirred at room temperature for 0.5 h. The reaction mixture is washed with water (50 mL) and brine (50 mL), dried over MgSO4, filtered, and concentrated under reduced pressure. Fractional distillation gives 12.0 g of methyl 5-bromo-1-methyl-1H-pyrrole-2-carboxylate as a yellow oil (64% yield). MS for C7H8NO2Br (ESI) (M)+ m/z 217.1.

Workup

  1. custompurged with nitrogen
  2. washThe reaction mixture is washed with water (50 mL) and brine (50 mL)
  3. dry with materialdried over MgSO4
  4. filtrationfiltered
  5. concentrationconcentrated under reduced pressure
  6. distillationFractional distillation

Sources & evidence

ORD record
ord-9fdb861bc22d48b19d27524853131180
Source dataset
uspto-grants-2003_07
Patent number
US06599916B2

Reaction notes

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