N-bromobutanimide → 4-Bromo-1-methyl-1H-pyrrole-2-carbonitrile

HRID 518928Notes

Reaction equation

HRID 518928 reaction equation
[Br:1]N1C(=O)CCC1=O.[CH3:9][N:10]1[CH:14]=[CH:13][CH:12]=[C:11]1[C:15]#[N:16]>CN(C)C=O>[Br:1][C:13]1[CH:12]=[C:11]([C:15]#[N:16])[N:10]([CH3:9])[CH:14]=1

Participants

4

Reactant 2

HCID 67184N-bromobutanimide2×HCID 20641111-Methylpyrrole-2-carbonitrile

Product 1

HCID 566989224-Bromo-1-methyl-1H-pyrrole-2-carbonitrile

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

N-Bromosuccinimide (6.2 g, 34.9 mmol) is added to a solution of 1-methyl-1H-pyrrole-2-carbonitrile (3.7 g, 34.9 mmol) in N,N-dimethylformamide (150 mL). The solution is stirred for 15 hours at ambient temperature. Another amount of N-bromosuccinimide (2.0 g, 11 mmol) is added and the mixture is stirred for 3 hours. The product is purified by chromatography over silica gel (ethyl acetate/heptane gradient) to obtain the expected product in the form of a solid.

Workup

  1. stirringthe mixture is stirred for 3 hours
  2. customThe product is purified by chromatography over silica gel (ethyl acetate/heptane gradient)

Sources & evidence

ORD record
ord-e1427a33270f4935982ced41166872ee
Source dataset
uspto-grants-2015_08
Patent number
US09115159B2

Reaction notes

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