Phosphorus oxychloride → 2-Chloro-3-iodo-5-nitropyridine

HRID 41975Notes

Reaction equation

HRID 41975 reaction equation
[I:1][C:2]1[C:3](O)=[N:4][CH:5]=[C:6]([N+:8]([O-:10])=[O:9])[CH:7]=1.O=P(Cl)(Cl)[Cl:14].P(Cl)(Cl)(Cl)(Cl)Cl>O>[Cl:14][C:3]1[C:2]([I:1])=[CH:7][C:6]([N+:8]([O-:10])=[O:9])=[CH:5][N:4]=1

Participants

5

Reactant 3

HCID 24813Phosphorus oxychlorideHCID 24819Phosphorus pentachlorideHCID 178526840HCID 178526840, compound

Product 1

HCID 111406392-Chloro-3-iodo-5-nitropyridineYield 69%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
140 °C

Procedure

A mixture of 3-iodo-5-nitropyridin-2-ol (37.60 mmol, 10 g), POCl3 (86.47 mmol, 7.94 ml) and PCl5 (48.87 mmol, 10.2 g) was heated at 140° C. for 45 minutes under argon atmosphere. The mixture was cooled at room temperature, poured slowly over iced-water and extracted with dichloromethane. The organic phase was washed with water, NaHCO3 aqueous solution and brine. The solvent was evaporated and the crude mixture was purified by chromatography over SiO2 eluting hexane/DCM mixtures affording 7.32 g (yield 69%) of the expected product.

Workup

  1. temperatureThe mixture was cooled at room temperature
  2. extractionextracted with dichloromethane
  3. washThe organic phase was washed with water, NaHCO3 aqueous solution and brine
  4. customThe solvent was evaporated
  5. customthe crude mixture was purified by chromatography over SiO2
  6. washeluting hexane/DCM

Sources & evidence

ORD record
ord-368a731995ad4219a40618e0ac9ec2b5
Source dataset
uspto-grants-2013_09
Patent number
US08536165B2

Reaction notes

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