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

HRID 1441853Notes

Reaction equation

HRID 1441853 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-0b4bb05d68b64df1b9fcb04c20f724a3
Source dataset
uspto-grants-2010_02
Patent number
US07655689B2

Reaction notes

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