Phosphorus oxychloride → 2,6-Dichloro-3-(trifluoromethyl)pyridine
Reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]([F:11])([F:10])[F:9])=[CH:4][N+:3]=1[O-].O=P(Cl)(Cl)[Cl:15]>>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]([F:11])([F:10])[F:9])=[C:4]([Cl:15])[N:3]=1Participants
3
Conditions
- Temperature
- 80 °C
Procedure
2-Chloro-5-trifluoromethyl-pyridine-N-oxide (17, 4 mmol) was dissolved in freshly distilled POCl3 (4.5 mL). The reaction mixture was heated to 80° C. for 17 h. After cooling to room temperature, the solvent was removed under reduced pressure. Ice was added, and the mixture was allowed to stand for 4 h. The mixture was partition between CH2Cl2 (50 mL) and saturated aqueous NaHCO3. Column chromatography afforded compound 18 as yellow oil (yield: 50%).
Workup
- temperatureAfter cooling to room temperature
- customthe solvent was removed under reduced pressure
- additionIce was added
- customThe mixture was partition between CH2Cl2 (50 mL) and saturated aqueous NaHCO3
Sources & evidence
- ORD record
- ord-a691fa28187f48039c08e3ba06d16e3f
- Source dataset
- uspto-grants-2013_04
- Patent number
- US08415357B2
Reaction notes
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