Thionyl Chloride → 2-Chloro-3-nitro-5-(trifluoromethyl)pyridine

HRID 1370096Notes

Reaction equation

HRID 1370096 reaction equation
O[C:2]1[C:7]([N+:8]([O-:10])=[O:9])=[CH:6][C:5]([C:11]([F:14])([F:13])[F:12])=[CH:4][N:3]=1.S(Cl)([Cl:17])=O>CN(C)C=O>[Cl:17][C:2]1[C:7]([N+:8]([O-:10])=[O:9])=[CH:6][C:5]([C:11]([F:14])([F:13])[F:12])=[CH:4][N:3]=1

Participants

4

Reactant 2

HCID 24386Thionyl ChlorideHCID 178526653HCID 178526653, compound

Product 1

HCID 47369502-Chloro-3-nitro-5-(trifluoromethyl)pyridine

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A mixture of 2-hydroxy-3-nitro-5-(trifluoromethyl)pyridine (5.0 g), thionyl chloride(28 mL) and N,N-dimethylformamide (3 mL) was heated under reflux for 5 hours. The reaction mixture was concentrated in vacuo, and ice was added to the residue. The mixture was extracted with a mixture of ethyl acetate and tetrahydrofuran. The separated organic layer was washed with brine, dried over.magnesium sulfate, and evaporated in vacuo. The residue was subjected to a silica gel column chromatography eluting with a mixture of n-hexane and ethyl acetate (5:1) and then to an aluminum oxide (activated, basic) column chromatography eluting with ethyl acetate to give 2-chloro-3-nitro-5-(trifluoromethyl)pyridine (4.89 g) as a yellow oil.

Workup

  1. temperaturewas heated
  2. temperatureunder reflux for 5 hours
  3. concentrationThe reaction mixture was concentrated in vacuo, and ice
  4. additionwas added to the residue
  5. extractionThe mixture was extracted with a mixture of ethyl acetate and tetrahydrofuran
  6. washThe separated organic layer was washed with brine
  7. customdried over
  8. custommagnesium sulfate, and evaporated in vacuo
  9. washeluting with a mixture of n-hexane and ethyl acetate (5:1)
  10. washto an aluminum oxide (activated, basic) column chromatography eluting with ethyl acetate

Sources & evidence

ORD record
ord-4e670c5ed68a47b5afa7171bdbe2f557
Source dataset
uspto-grants-2003_06
Patent number
US06582351B1

Reaction notes

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