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

HRID 2110475Notes

Reaction equation

HRID 2110475 reaction equation
O[C:2]1[C:7]([I:8])=[CH:6][C:5]([N+:9]([O-:11])=[O:10])=[CH:4][N:3]=1.P(Cl)(Cl)(Cl)(Cl)[Cl:13].P(Cl)(Cl)(Cl)=O>>[Cl:13][C:2]1[C:7]([I:8])=[CH:6][C:5]([N+:9]([O-:11])=[O:10])=[CH:4][N:3]=1

Participants

4

Reactant 3

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

Product 1

HCID 111406392-Chloro-3-iodo-5-nitropyridineYield 83.3%

Conditions

Temperature
140 °C

Procedure

2-Hydroxy-3-iodo-5-nitropyridine (2.55 g, 9.5 mmol), phosphorous pentachloride (2.60 g, 12 mmol) and phosphorous oxychloride (2 mL) were combined in a flask under nitrogen and heated to 140° C. for 45 mins. The cooled reaction mixture was poured over ice to give a solid which was partitioned between CH2Cl2 and water. The organic layer was separated, washed with brine, dried (MgSO4), filtered, and the solvent was removed in vacuo to give compound 765B (2.25 g, 83%) as a yellow solid. HPLC: 98.5% at 2.75 min(YMC S5 ODS column) eluting with 10-90% aqueous methanol containing 0.2% phosphoric acid over a 4 min gradient monitoring at 220 nm.

Workup

  1. customThe cooled reaction mixture
  2. additionwas poured over ice
  3. customto give a solid which
  4. customwas partitioned between CH2Cl2 and water
  5. customThe organic layer was separated
  6. washwashed with brine
  7. dry with materialdried (MgSO4)
  8. filtrationfiltered
  9. customthe solvent was removed in vacuo

Sources & evidence

ORD record
ord-783929be44b347679408bbdf91c61f0d
Source dataset
uspto-grants-2009_04
Patent number
US07517904B2

Reaction notes

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