Phosphorus oxychloride → 4-Chloro-5-iodo-alpha,alpha,alpha-trifluoro-2-picoline

HRID 2098018Notes

Reaction equation

HRID 2098018 reaction equation
[I:1][C:2]1[C:3](O)=[CH:4][C:5]([C:8]([F:11])([F:10])[F:9])=[N:6][CH:7]=1.O=P(Cl)(Cl)[Cl:15]>>[Cl:15][C:3]1[C:2]([I:1])=[CH:7][N:6]=[C:5]([C:8]([F:11])([F:10])[F:9])[CH:4]=1

Participants

3

Reactant 2

HCID 24813Phosphorus oxychlorideHCID 178516139HCID 178516139, compound

Product 1

HCID 687560594-Chloro-5-iodo-alpha,alpha,alpha-trifluoro-2-picoline

Procedure

A solution of 5-iodo-2-(trifluoromethyl)pyridin-4-ol (4.8 g, 16.6 mmol) in POCl3 (30 mL) was heated to 100° C. for 30 minutes. The resulting solution was concentrated under vacuum and the residue was neutralized by the addition of ice and aqueous potassium carbonate. The solution was extracted with ethyl acetate, dried (Na2SO4), filtered and concentrated under vacuum to give 4-chloro-5-iodo-2-(trifluoromethyl)pyridine. Retention time (min)=2.594, method [1], MS (ESI) 307.9 (M+H).

Workup

  1. concentrationThe resulting solution was concentrated under vacuum
  2. additionthe residue was neutralized by the addition of ice and aqueous potassium carbonate
  3. extractionThe solution was extracted with ethyl acetate
  4. dry with materialdried (Na2SO4)
  5. filtrationfiltered
  6. concentrationconcentrated under vacuum

Sources & evidence

ORD record
ord-d3df14058b9644da868c362dc32a2b26
Source dataset
uspto-grants-2013_05
Patent number
US08450363B2

Reaction notes

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