4-Nitrophenol → 2-(4-Nitrophenoxy)-3-chloro-5-trifluoromethyl pyridine

HRID 637986Notes

Reaction equation

HRID 637986 reaction equation
Cl[C:2]1[C:7]([Cl:8])=[CH:6][C:5]([C:9]([F:12])([F:11])[F:10])=[CH:4][N:3]=1.[N+:13]([C:16]1[CH:21]=[CH:20][C:19]([OH:22])=[CH:18][CH:17]=1)([O-:15])=[O:14].C(=O)([O-])[O-].[K+].[K+]>C(C(C)=O)C>[Cl:8][C:7]1[C:2]([O:22][C:19]2[CH:20]=[CH:21][C:16]([N+:13]([O-:15])=[O:14])=[CH:17][CH:18]=2)=[N:3][CH:4]=[C:5]([C:9]([F:12])([F:11])[F:10])[CH:6]=1

Participants

5

Reactant 3

HCID 9804-NitrophenolHCID 11430Potassium CarbonateHCID 1122342,3-Dichloro-5-(trifluoromethyl)pyridine

Product 1

HCID 27757362-(4-Nitrophenoxy)-3-chloro-5-trifluoromethyl pyridine

Reagents, catalysts & solvents 1

HCID 6569Methyl Ethyl KetoneSolvent

Procedure

2,3-Dichloro-5-trifluoromethylpyridine (2.16 g, 0.01M) and 4-nitrophenol (1.53 g, 0.011M) were mixed in methyl ethyl ketone (10 ml) containing anhydrous potassium carbonate (2.0 g) and heated at the reflux temperature for 10 hours. The cooled mixture was filtered to remove the solid matter and the filtrate concentrated by evaporation of the solvent under reduced pressure. The residue was triturated with diethyl ether and 3-chloro-5-trifluoromethyl-2-(4-nitrophenoxy)pyridine collected as a buff coloured solid (0.75 g), m.p. 98°-100° C.

Workup

  1. temperatureheated at the reflux temperature for 10 hours
  2. filtrationThe cooled mixture was filtered
  3. customto remove the solid matter
  4. concentrationthe filtrate concentrated by evaporation of the solvent under reduced pressure
  5. customThe residue was triturated with diethyl ether and 3-chloro-5-trifluoromethyl-2-(4-nitrophenoxy)pyridine
  6. customcollected as a buff

Sources & evidence

ORD record
ord-4e0048e08e90433ebf5a94b79c9de9c5
Source dataset
uspto-grants-1985_12
Patent number
US04559353

Reaction notes

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