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

HRID 41984Notes

Reaction equation

HRID 41984 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 (37.6 mmol, 10 g), POCl3 (86.47 mmol, 7.94 ml) and PCl5 (48.87 mmol, 10.2 g) was heated at 140° C. for 1 h, under argon atmosphere. The crude mixture was poured into a mixture of ice and water and extracted with DCM. The solid residue was purified by chromatography over SiO2 eluting with hexane/dichloromethane mixtures affording 2-chloro-3-iodo-5-nitropyridine (7.32 g, yield 69%) of the expected product.

Workup

  1. extractionextracted with DCM
  2. customThe solid residue was purified by chromatography over SiO2 eluting with hexane/dichloromethane

Sources & evidence

ORD record
ord-36430576da66434ab6f7608884f5d2a3
Source dataset
uspto-grants-2013_09
Patent number
US08536165B2

Reaction notes

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