Phosphorus oxychloride → 5-Bromo-2-chloro-3-nitropyridine

HRID 2417006Notes

Reaction equation

HRID 2417006 reaction equation
O[C:2]1[C:7]([N+:8]([O-:10])=[O:9])=[CH:6][C:5]([Br:11])=[CH:4][N:3]=1.P(Cl)(Cl)([Cl:14])=O.P(Cl)(Cl)(Cl)(Cl)Cl>>[Br:11][C:5]1[CH:6]=[C:7]([N+:8]([O-:10])=[O:9])[C:2]([Cl:14])=[N:3][CH:4]=1

Participants

4

Reactant 3

HCID 24813Phosphorus oxychlorideHCID 24819Phosphorus pentachlorideHCID 178418997HCID 178418997, compound

Product 1

HCID 70194125-Bromo-2-chloro-3-nitropyridine

Conditions

Temperature
110 °C

Procedure

2-Hydroxy-3-nitro-5-bromopyridine (10 g) was combined with 25 mL of phosphorus oxychloride and 5 g of phosphorus pentachloride. The mixture was heated to 110° C. for 2 h, then cooled to room temperature and poured into ice-water and stirred 30 min. The mixture was extracted with CHCl3, then the combined organics were dried (MgSO4) and concentrated in vacuo. Purification by chromatography through a short plug of SiO2, eluting with 4:1 hexanes:EtOAc afforded 6.72 g of 5-bromo-2-chloro-3-nitro-pyridine.

Workup

  1. temperaturecooled to room temperature
  2. extractionThe mixture was extracted with CHCl3
  3. dry with materialthe combined organics were dried (MgSO4)
  4. concentrationconcentrated in vacuo
  5. customPurification by chromatography through a short plug of SiO2
  6. washeluting with 4:1 hexanes

Sources & evidence

ORD record
ord-51ddc36708c14e97bb2a5d89fc9b52a8
Source dataset
uspto-grants-2004_11
Patent number
US06825184B2

Reaction notes

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