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

HRID 545071Notes

Reaction equation

HRID 545071 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:17])=O>>[Cl:17][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

3

Reactant 2

HCID 24813Phosphorus oxychlorideHCID 178526837HCID 178526837, compound

Product 1

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

Procedure

Heat a mixture of 5-nitro-3-trifluoromethyl-pyridin-2-ol (416 mg, 2.0 mmol) and phosphorus oxychloride (1 mL) at 85° C. for 18 hours. Cool the mixture and remove the volatiles by rotary evaporation. Dissolve the residue in EtOAc (15 mL) and wash with water (10 mL), saturated NaHCO3(aq) (10 mL) and brine (10 mL). Dry the organic extract over MgSO4 and remove the solvent under reduced pressure to yield the title compound.

Workup

  1. temperatureHeat
  2. temperatureCool the mixture
  3. customremove the volatiles
  4. customby rotary evaporation
  5. dissolutionDissolve the residue in EtOAc (15 mL)
  6. washwash with water (10 mL), saturated NaHCO3(aq) (10 mL) and brine (10 mL)
  7. customDry the
  8. extractionorganic extract over MgSO4
  9. customremove the solvent under reduced pressure

Sources & evidence

ORD record
ord-a9217d6943f1428abd0c5d0711b0b4d4
Source dataset
uspto-grants-2011_05
Patent number
US07935702B2

Reaction notes

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