Phosphorus oxychloride → 2,6-Dichloro-3-(trifluoromethyl)pyridine

HRID 659983Notes

Reaction equation

HRID 659983 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]=1

Participants

3

Reactant 2

HCID 24813Phosphorus oxychlorideHCID 154483422-Chloro-5-(trifluoromethyl)pyridine 1-oxide

Product 1

HCID 18103372,6-Dichloro-3-(trifluoromethyl)pyridineYield 50%

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

  1. temperatureAfter cooling to room temperature
  2. customthe solvent was removed under reduced pressure
  3. additionIce was added
  4. customThe mixture was partition between CH2Cl2 (50 mL) and saturated aqueous NaHCO3

Sources & evidence

ORD record
ord-ebed38c8dee740a397bdf40db21b9ab9
Source dataset
uspto-grants-2011_12
Patent number
US08084454B2

Reaction notes

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