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

HRID 1508495Notes

Reaction equation

HRID 1508495 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)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-carboxylate

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Conditions

Temperature
0 °C

Procedure

To a solution of methyl 1-methyl-1H-pyrrole-2-carboxylate (100 mg, 0.719 mmol) in CHCl3 (5 mL) at 0° C. was added N-bromosuccinimide (128 mg, 0.719 mmol). The reaction was stirred at 0° C. for 5 min. The reaction was allowed to warm to room temperature and stirred overnight. The reaction mixture was filtered and concentrated in vacuo. The residue was purified by preparative TLC (1000 μm, hexanes/EtOAc (9:1)) to give methyl 5-bromo-1-methyl-1H-pyrrole-2-carboxylate. 1H NMR (500 MHz, CDCl3): δ 6.94 (d, J=4.2 Hz, 1H); 6.21 (d, J=4.1 Hz, 1H); 3.94 (s, 3H); 3.82 (s, 3H).

Workup

  1. temperatureto warm to room temperature
  2. stirringstirred overnight
  3. filtrationThe reaction mixture was filtered
  4. concentrationconcentrated in vacuo
  5. customThe residue was purified by preparative TLC (1000 μm, hexanes/EtOAc (9:1))

Sources & evidence

ORD record
ord-af2874c47e57441e89d01a1f1e7b3bbd
Source dataset
uspto-grants-2015_12
Patent number
US09221834B2

Reaction notes

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