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

HRID 1458237Notes

Reaction equation

HRID 1458237 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 methylate solution were added with stirring at 0°-5° C. in the course of 20 minutes to 15 g (0.06 mol) of 2,3,6-trichloro-5-trifluoromethylpyridine in 200 ml of methyl tert-butyl ether, and stirring was continued for 30 minutes at the same temperature. After the mixture had been heated to 20° C., the fine precipitate which had formed was filtered off with suction and washed using methyl tert-butyl ether. The organic filtrate was washed with water, dried and concentrated, giving 14.3 g (97% of theory) of the title compound of η25D =1.4890 (Table III, No. 3.001).

Workup

  1. customthe fine precipitate which had formed
  2. filtrationwas filtered off with suction
  3. washwashed
  4. washThe organic filtrate was washed with water
  5. customdried
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-8347e61646c5449e9ea75d47463f8775
Source dataset
uspto-grants-1998_12
Patent number
US05849920

Reaction notes

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