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

HRID 2354012Notes

Reaction equation

HRID 2354012 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-4d8119906f174315ad03a46dd6bd7ca9
Source dataset
uspto-grants-2010_07
Patent number
US07750150B2

Reaction notes

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