Water → 5-Chloro-2-iodo-3-nitropyridine

HRID 1898103Notes

Reaction equation

HRID 1898103 reaction equation
Br[C:2]1[C:7]([N+:8]([O-:10])=[O:9])=[CH:6][C:5]([Cl:11])=[CH:4][N:3]=1.[Na+].[I-:13].O>CN(C=O)C>[Cl:11][C:5]1[CH:6]=[C:7]([N+:8]([O-:10])=[O:9])[C:2]([I:13])=[N:3][CH:4]=1

Participants

5

Reactant 3

HCID 962WaterHCID 5238Sodium IodideHCID 2806812-Bromo-5-chloro-3-nitropyridine

Product 1

HCID 579421085-Chloro-2-iodo-3-nitropyridine

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
97.5 °C

Procedure

To a stirred mixture of 2-bromo-5-chloro-3-nitro-pyridine (2.5 g, 10.5 mmol) in anhydrous DMF (20 mL) was added NaI (12.0 g, 80 mmol) was added in one portion and the resulting mixture was heated at 95-100° C. for 2 days. The reaction mixture was cooled to room tempearture and poured into water. It was then extracted with EtOAc and the combined extracts were washed with aqueous 10% Na2S2O3. The combined extracts were dried (Na2SO4), filtered and concentrated under reduced pressure. The residue was purified by flash column chromatography on silica gel to provide 5-Chloro-2-iodo-3-nitro-pyridine. Mass spectrum m/z: 285.2 (M+H).

Workup

  1. additionwas added in one portion
  2. temperatureThe reaction mixture was cooled to room tempearture
  3. extractionIt was then extracted with EtOAc
  4. washthe combined extracts were washed with aqueous 10% Na2S2O3
  5. dry with materialThe combined extracts were dried (Na2SO4)
  6. filtrationfiltered
  7. concentrationconcentrated under reduced pressure
  8. customThe residue was purified by flash column chromatography on silica gel

Sources & evidence

ORD record
ord-8fe7f9b96d064beda2d024ef7efb63e2
Source dataset
uspto-grants-2013_08
Patent number
US08519135B2

Reaction notes

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