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

HRID 2298375Notes

Reaction equation

HRID 2298375 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-10e734bd774d425189c6d7b8e34c42df
Source dataset
uspto-grants-2002_12
Patent number
US06492385B2

Reaction notes

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