Chlorine → 3-Chloro-5-(trifluoromethyl)pyridin-2-ol

HRID 464127

Reaction equation

HRID 464127 reaction equation
[F:1][C:2]([F:11])([F:10])[C:3]1[CH:4]=[CH:5][C:6](=[O:9])[NH:7][CH:8]=1.[Cl:12]Cl>C(Cl)(Cl)Cl>[Cl:12][C:5]1[C:6](=[O:9])[NH:7][CH:8]=[C:3]([C:2]([F:1])([F:10])[F:11])[CH:4]=1

Participants

4

Reactant 2

HCID 24526ChlorineHCID 1474432-Hydroxy-5-(trifluoromethyl)pyridine

Product 1

HCID 7254363-Chloro-5-(trifluoromethyl)pyridin-2-ol

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

[A] 0.2 g of 5-trifluoromethyl-2-pyridone was dissolved in 20 ml of chloroform, and chlorine gas was pressed through the solution at 50° C. for 1 hour while stirring. After completion of the reaction, the chloroform was distilled off, and recrystallization was performed from a mixed solvent of toluene and n-hexane to obtain 0.15 g of the titled compound having a melting point of 144° to 147° C. The recrystallization was further repeated to obtain 0.09 g of the titled compound having a melting point of 165° to 166° C.

Workup

  1. customAfter completion of the reaction
  2. distillationthe chloroform was distilled off
  3. customrecrystallization

Sources & evidence

ORD record
ord-3d65025180d541d09500a4a4ae4da374
Source dataset
uspto-grants-1985_10
Patent number
US04546191

Linked notes

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