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

HRID 251941Notes

Reaction equation

HRID 251941 reaction equation
[Cl:1][C:2]1[C:3]([N:8]2[CH:12]=[CH:11][CH:10]=[C:9]2[CH:13]=[O:14])=[N:4][CH:5]=[CH:6][CH:7]=1.[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:3]2[C:2]([Cl:1])=[CH:7][CH:6]=[CH:5][N:4]=2)[CH:12]=1

Participants

5

Reactant 3

HCID 962WaterHCID 67184N-bromobutanimideHCID 587620783-chloro-2-(2-formyl-1H-pyrrol-1-yl)pyridine

Product 1

HCID 866325474-bromo-1-(3-chloro-2-pyridinyl)-1H-pyrrole-2-carbaldehydeYield 91.7%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of 1.5 g of 3-chloro-2-(2-formyl-1H-pyrrol-1-yl)pyridine in 20 ml of N,N-dimethylformamide, 1.3 g of N-bromosuccinimide was added. The mixture was stirred at room temperature for 3 hours. Water was poured into the reaction mixture, and a deposited precipitate was collected by filtration to obtain 1.9 g of 4-bromo-1-(3-chloro-2-pyridinyl)-1H-pyrrole-2-carbaldehyde of the formula:

Workup

  1. filtrationa deposited precipitate was collected by filtration

Sources & evidence

ORD record
ord-316b965cf8064049b437becfb58c86f3
Source dataset
uspto-grants-2011_01
Patent number
US07867949B2

Reaction notes

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