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

HRID 1354254Notes

Reaction equation

HRID 1354254 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]>O>[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

5

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%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

2,4-Dichloro-6-methyl-3-nitropyridine (30 g, 144.9 mmol) was dissolved in 2,2,2-trifluoroethanol (250 mL), and potassium carbonate (50 g, 361.8 mmol) was added thereto, followed by reflux for 21 hours. The reaction mixture was diluted with water, and then subjected to extraction with chloroform. The organic layer was washed with saturated brine and then dried over sodium sulfate anhydrate, followed by concentration under reduced pressure, to thereby yield 2,4-bis(2,2,2-trifluoroethoxy)-6-methyl-3-nitropyridine (45.40 g, yield 94%) as a pale yellow solid.

Workup

  1. temperatureby reflux for 21 hours
  2. extractionsubjected to extraction with chloroform
  3. washThe organic layer was washed with saturated brine
  4. dry with materialdried over sodium sulfate anhydrate
  5. concentrationfollowed by concentration under reduced pressure

Sources & evidence

ORD record
ord-0133cd38b305498bbce0ef241a923947
Source dataset
uspto-grants-2007_05
Patent number
US07223764B2

Reaction notes

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