2,6-Dichloro-4-(trifluoromethyl)pyridine → 2-Chloro-6-methoxy-4-(trifluoromethyl)pyridine

HRID 339807

Reaction equation

HRID 339807 reaction equation
[Cl:1][C:2]1[CH:7]=[C:6]([C:8]([F:11])([F:10])[F:9])[CH:5]=[C:4](Cl)[N:3]=1.[OH-:13].[Na+].[CH3:15]O>CO>[CH3:15][O:13][C:4]1[CH:5]=[C:6]([C:8]([F:11])([F:10])[F:9])[CH:7]=[C:2]([Cl:1])[N:3]=1

Participants

4

Reactant 2

HCID 5209682,6-Dichloro-4-(trifluoromethyl)pyridineHCID 23721981Sodium hydroxide methanol

Product 1

HCID 568323142-Chloro-6-methoxy-4-(trifluoromethyl)pyridineYield 99.9%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
50 °C

Procedure

To a solution of 2,6-dichloro-4-trifluoromethylpyridine (10 g, 46.3 mmol) in methanol (200 mL) was added 25% NaOH/MeOH (12.5 g, 13.2 mL, 231 mmol), which was then stirred at 50° C. for 2 h and then at room temperature overnight. The reaction mixture was extracted with pentane, and the extract was concentrated in vacuo to afford 2-methoxy-6-chloro-4-trifluoromethylpyridine (9.79 g), used without further purification.

Workup

  1. customat room temperature
  2. customovernight
  3. extractionThe reaction mixture was extracted with pentane
  4. concentrationthe extract was concentrated in vacuo

Sources & evidence

ORD record
ord-b5c7d2dfeb7549569c8b8a811368072d
Source dataset
uspto-grants-2014_11
Patent number
US08895568B2

Linked notes

Loading…