2,3,6-Trichloro-5-(trifluoromethyl)pyridine → 2,5-Dichloro-6-methoxy-3-trifluoromethylpyridine

HRID 1871867Notes

Reaction equation

HRID 1871867 reaction equation
[CH3:1][O-:2].[Na+].Cl[C:5]1[C:10]([Cl:11])=[CH:9][C:8]([C:12]([F:15])([F:14])[F:13])=[C:7]([Cl:16])[N:6]=1>C(OC)(C)(C)C>[Cl:16][C:7]1[C:8]([C:12]([F:15])([F:14])[F:13])=[CH:9][C:10]([Cl:11])=[C:5]([O:2][CH3:1])[N:6]=1

Participants

4

Reactant 2

HCID 27606902,3,6-Trichloro-5-(trifluoromethyl)pyridineHCID 10942334Sodium Methoxide

Product 1

HCID 186895102,5-Dichloro-6-methoxy-3-trifluoromethylpyridine

Reagents, catalysts & solvents 1

HCID 15413tert-Butyl methyl etherSolvent

Conditions

Temperature
20 °C

Procedure

10.8 g (0.06 mol) of 30% strength sodium methoxide solution were added to 15 g (0.06 mol) of 2,3,6-trichloro-5-trifluoromethylpyridine in 200 ml of methyl tert-butyl ether at 0-5° C. with stirring in the course of 20 minutes and the mixture was subsequently stirred at the same temperature for 30 minutes. After warming to 20° C., the resulting fine precipitate was filtered off with suction and washed with methyl tert-butyl ether. The organic filtrate was washed with water, dried and concentrated, 14.3 g (97% of theory) of the title compound of n25D =1.4890 being obtained.

Workup

  1. stirringthe mixture was subsequently stirred at the same temperature for 30 minutes
  2. filtrationthe resulting fine precipitate was filtered off with suction
  3. washwashed with methyl tert-butyl ether
  4. washThe organic filtrate was washed with water
  5. customdried
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-073c19489dc54292b2d1dc8b874290c5
Source dataset
uspto-grants-2000_08
Patent number
US06107253

Reaction notes

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