Water → 4-bromo-1-(3-chloro-4-pyridinyl)-1H-pyrrole-2-carbaldehyde

HRID 251996Notes

Reaction equation

HRID 251996 reaction equation
[Cl:1][C:2]1[CH:3]=[N:4][CH:5]=[CH:6][C:7]=1[N:8]1[CH:12]=[CH:11][CH:10]=[C:9]1[CH:13]=[O:14].[Br:15]N1C(=O)CCC1=O.O>CN(C)C=O>[Br:15][C:11]1[CH:10]=[C:9]([CH:13]=[O:14])[N:8]([C:7]2[CH:6]=[CH:5][N:4]=[CH:3][C:2]=2[Cl:1])[CH:12]=1

Participants

5

Reactant 3

HCID 962WaterHCID 67184N-bromobutanimideHCID 866325591-(3-chloro-4-pyridinyl)-1H-pyrrole-2-carbaldehyde

Product 1

HCID 866325604-bromo-1-(3-chloro-4-pyridinyl)-1H-pyrrole-2-carbaldehydeYield 29.4%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of 2.95 g of 1-(3-chloro-4-pyridinyl)-1H-pyrrole-2-carbaldehyde in 20 ml of N,N-dimethylformamide was added 2.66 g of N-bromosuccinimide. The resulting mixture was stirred at room temperature for 10 hours. Water was poured into the reaction mixture, and a deposited precipitate was collected by filtration to obtain 1.2 g of 4-bromo-1-(3-chloro-4-pyridinyl)-1H-pyrrole-2-carbaldehyde of the formula:

Workup

  1. filtrationa deposited precipitate was collected by filtration

Sources & evidence

ORD record
ord-5dff8bfbe2ff4ffe9faeae71b432ca78
Source dataset
uspto-grants-2011_01
Patent number
US07867949B2

Reaction notes

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