Phosphorus oxychloride → 4-Chloro-5-iodonicotinonitrile

HRID 506173Notes

Reaction equation

HRID 506173 reaction equation
O[C:2]1[C:7]([C:8]#[N:9])=[CH:6][N:5]=[CH:4][C:3]=1[I:10].O=P(Cl)(Cl)[Cl:13]>>[Cl:13][C:2]1[C:7]([C:8]#[N:9])=[CH:6][N:5]=[CH:4][C:3]=1[I:10]

Participants

3

Reactant 2

HCID 24813Phosphorus oxychlorideHCID 178510339HCID 178510339, compound

Product 1

HCID 594311594-Chloro-5-iodonicotinonitrileYield 75%

Conditions

Temperature
100 °C

Procedure

A mixture of 4-hydroxy-5-iodonicotinonitrile (57.5 g, 234 mmol) and POCl3 (200 mL) was heated at 100° C. for 2 hours, cooled to room temperature and evaporated to remove excess POCl3. The residue was cooled in an ice-water bath, adjusted to pH 8-9 with aqueous 10 N NaOH and extracted with ethyl acetate. The combined organics were washed with water and brine, dried over magnesium sulfate and concentrated. The resulting solid residue was washed with a minimum amount of methanol and methylene chloride to give 46.5 g (75%) of 4-chloro-5-iodonicotinonitrile as a tan solid. Melting range: 120-122° C.

Workup

  1. temperaturecooled to room temperature
  2. customevaporated
  3. customto remove excess POCl3
  4. temperatureThe residue was cooled in an ice-water bath
  5. extractionextracted with ethyl acetate
  6. washThe combined organics were washed with water and brine
  7. dry with materialdried over magnesium sulfate
  8. concentrationconcentrated
  9. washThe resulting solid residue was washed with a minimum amount of methanol and methylene chloride

Sources & evidence

ORD record
ord-ad1e09b81c2d467d8431361fd21df552
Source dataset
uspto-grants-2010_08
Patent number
US07781591B2

Reaction notes

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