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

HRID 77729Notes

Reaction equation

HRID 77729 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.P(Cl)(Cl)([Cl:14])=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

3

Reactant 2

HCID 24813Phosphorus oxychlorideHCID 178526840HCID 178526840, compound

Product 1

HCID 111406392-Chloro-3-iodo-5-nitropyridine

Procedure

3-Iodo-5-nitropyridin-2-ol (3.00 g, 0.0113 mol) was heated to reflux in phosphoryl chloride (15 mL, 0.1609 mol) for 4 hours. The reaction was quenched in ice/water and was neutralized with Na2CO3. The reaction was extracted with ethyl acetate and the organic extracts were washed with water, saturated NaCl, dried (MgSO4) and stripped in vacuo to give the product, which was used in the next reaction without purification.

Workup

  1. customThe reaction was quenched in ice/water
  2. extractionThe reaction was extracted with ethyl acetate
  3. washthe organic extracts were washed with water, saturated NaCl
  4. dry with materialdried (MgSO4)
  5. customto give the product, which
  6. customwas used in the next reaction without purification

Sources & evidence

ORD record
ord-4f25e1129fd24f0cb896bcefa30ff55b
Source dataset
uspto-grants-2014_09
Patent number
US08841318B2

Reaction notes

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