2,2,2-Trifluoroethanol → 6-Methyl-3-nitro-2,4-bis(2,2,2-trifluoroethoxy)pyridine

HRID 1896052Notes

Reaction equation

HRID 1896052 reaction equation
Cl[C:2]1[C:7]([N+:8]([O-:10])=[O:9])=[C:6](Cl)[CH:5]=[C:4]([CH3:12])[N:3]=1.[C:13](=[O:16])([O-])[O-].[K+].[K+].[F:19][C:20]([F:24])([F:23])[CH2:21][OH:22]>>[F:19][C:20]([F:24])([F:23])[CH2:21][O:22][C:2]1[C:7]([N+:8]([O-:10])=[O:9])=[C:6]([O:16][CH2:13][C:20]([F:24])([F:23])[F:19])[CH:5]=[C:4]([CH3:12])[N:3]=1

Participants

4

Reactant 3

HCID 64092,2,2-TrifluoroethanolHCID 11430Potassium CarbonateHCID 27848192,4-Dichloro-6-methyl-3-nitropyridine

Product 1

HCID 230924206-Methyl-3-nitro-2,4-bis(2,2,2-trifluoroethoxy)pyridineYield 94%

Procedure

2,4-Dichloro-6-methyl-3-nitropyridine (30 g, 144.9 mmol) was dissolved in 2,2,2-trifluoroethanol (250 mL), followed by the addition of potassium carbonate (50 g, 361.8 mmol). The mixture was subjected to heating under reflux for 21 hours. The reaction mixture was extracted with chloroform-water. The organic layer was washed with a saturated aqueous solution of sodium chloride (brine), dried over anhydrous sodium sulfate, and concentrated under reduced pressure to obtain the title compound (45.40 g, 94%) as a pale yellow oil.

Workup

  1. temperatureto heating
  2. temperatureunder reflux for 21 hours
  3. extractionThe reaction mixture was extracted with chloroform-water
  4. washThe organic layer was washed with a saturated aqueous solution of sodium chloride (brine)
  5. dry with materialdried over anhydrous sodium sulfate
  6. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-4ea11502680344d19ca84cc18605ae43
Source dataset
uspto-grants-2013_08
Patent number
US08518936B2

Reaction notes

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