Phosphorus oxychloride → 2-Chloro-3-nitro-5-(trifluoromethyl)pyridine

HRID 533661Notes

Reaction equation

HRID 533661 reaction equation
[N+:1]([C:4]1[C:5](O)=[N:6][CH:7]=[C:8]([C:10]([F:13])([F:12])[F:11])[CH:9]=1)([O-:3])=[O:2].P(Cl)(Cl)([Cl:17])=O>CN(C=O)C>[Cl:17][C:5]1[C:4]([N+:1]([O-:3])=[O:2])=[CH:9][C:8]([C:10]([F:13])([F:12])[F:11])=[CH:7][N:6]=1

Participants

4

Reactant 2

HCID 24813Phosphorus oxychlorideHCID 178526653HCID 178526653, compound

Product 1

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

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideCatalyst

Conditions

Temperature
105 °C

Procedure

To a mixture of 3-nitro-5-trifluoromethylpyridin-2-ol (3.2 g) and DMF (1 drop), phosphorous oxychloride (8.2 ml) was added at room temperature. The mixture was heated to 105° C., and stirred with heating for 2 days. The reaction mixture was cooled to room temperature, and then the reaction mixture was poured into ice, and extracted with ethyl acetate. The organic layer was dried over sodium sulfate, and concentrated under reduced pressure to give 2.5 g of 2-chloro-3-nitro-5-trifluoromethylpyridine.

Workup

  1. additionwas added at room temperature
  2. temperaturewith heating for 2 days
  3. temperatureThe reaction mixture was cooled to room temperature
  4. additionthe reaction mixture was poured into ice
  5. extractionextracted with ethyl acetate
  6. dry with materialThe organic layer was dried over sodium sulfate
  7. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-c005d64d7dbc4fa081c93e12cbe5b9bf
Source dataset
uspto-grants-2014_10
Patent number
US08853238B2

Reaction notes

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