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

HRID 1848944Notes

Reaction equation

HRID 1848944 reaction equation
[N+:1]([C:4]1[CH:5]=[C:6]([C:11]([F:14])([F:13])[F:12])[C:7](O)=[N:8][CH:9]=1)([O-:3])=[O:2].P(Cl)(Cl)(Cl)(Cl)[Cl:16].P(Cl)(Cl)(Cl)=O>>[Cl:16][C:7]1[C:6]([C:11]([F:14])([F:13])[F:12])=[CH:5][C:4]([N+:1]([O-:3])=[O:2])=[CH:9][N:8]=1

Participants

4

Reactant 3

HCID 24813Phosphorus oxychlorideHCID 24819Phosphorus pentachlorideHCID 178526837HCID 178526837, compound

Product 1

HCID 38491402-Chloro-5-nitro-3-(trifluoromethyl)pyridine

Procedure

A mixture of EXAMPLE 405A (1.69 g), phosphorus pentachloride (2.03 g), and phosphoryl trichloride (0.97 mL) was heated at 90° C. for 3 hours. After cooling, the reaction mixture was poured into ice, and extracted with ethyl acetate three times. The extract was washed with brine, dried over MgSO4, filtered, and concentrated under reduced pressure. The residue was purified by flash column chromatography on silica gel eluting with 1:9 ethyl acetate\hexanes to give the title compound.

Workup

  1. temperatureAfter cooling
  2. additionthe reaction mixture was poured into ice
  3. extractionextracted with ethyl acetate three times
  4. washThe extract was washed with brine
  5. dry with materialdried over MgSO4
  6. filtrationfiltered
  7. concentrationconcentrated under reduced pressure
  8. customThe residue was purified by flash column chromatography on silica gel eluting with 1:9 ethyl acetate\hexanes

Sources & evidence

ORD record
ord-f3eb73f831014998be320e2750818473
Source dataset
uspto-grants-2015_02
Patent number
US08952157B2

Reaction notes

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