Water → 4-bromo-5-chloro-1-(3-chloro-2-pyridinyl)-1H-pyrrole-2-carbaldehyde

HRID 251998Notes

Reaction equation

HRID 251998 reaction equation
[Cl:1][C:2]1[C:3]([N:8]2[CH:12]=[C:11]([Br:13])[CH:10]=[C:9]2[CH:14]=[O:15])=[N:4][CH:5]=[CH:6][CH:7]=1.[Cl:16]N1C(=O)CCC1=O.O>O1CCCC1>[Br:13][C:11]1[CH:10]=[C:9]([CH:14]=[O:15])[N:8]([C:3]2[C:2]([Cl:1])=[CH:7][CH:6]=[CH:5][N:4]=2)[C:12]=1[Cl:16]

Participants

5

Reactant 3

HCID 962WaterHCID 31398ChlorosuccinimideHCID 866325474-bromo-1-(3-chloro-2-pyridinyl)-1H-pyrrole-2-carbaldehyde

Product 1

HCID 866325614-bromo-5-chloro-1-(3-chloro-2-pyridinyl)-1H-pyrrole-2-carbaldehydeYield 74.4%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 3.0 g of 3-chloro-2-(4-bromo-2-formyl-1H-pyrrol-1-yl)-pyridine in 30 ml of tetrahydrofuran was added 1.5 g of N-chlorosuccinimide. The resulting mixture was stirred at room temperature for 2 days. Water was poured into the reaction mixture, and the mixture was extracted with ethyl acetate two times. The organic layers were combined, washed with an aqueous saturated sodium chloride solution, dried over anhydrous magnesium sulfate, and concentrated under reduced pressure. The residue was subjected to silica gel column chromatography to obtain 2.5 g of 4-bromo-5-chloro-1-(3-chloro-2-pyridinyl)-1H-pyrrole-2-carbaldehyde of the formula:

Workup

  1. extractionthe mixture was extracted with ethyl acetate two times
  2. washwashed with an aqueous saturated sodium chloride solution
  3. dry with materialdried over anhydrous magnesium sulfate
  4. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-db438faaddf546ceb91542fc923b6732
Source dataset
uspto-grants-2011_01
Patent number
US07867949B2

Reaction notes

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