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

HRID 1519806Notes

Reaction equation

HRID 1519806 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-9823bd31297c4e079e6f80b2e97a58a5
Source dataset
uspto-grants-2015_07
Patent number
US09073891B2

Reaction notes

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