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

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

Reactant 2

HCID 24813Phosphorus oxychloride

HCID 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

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

Sources & evidence

ORD record: ord-d3df14058b9644da868c362dc32a2b26
Source dataset: uspto-grants-2013_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08450363B2

Reaction notes

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