Water → 2-Chloro-3-nitro-5-(trifluoromethyl)pyridine

HRID 1943655Notes

Reaction equation

HRID 1943655 reaction equation
[N+:1]([C:4]1[C:5](O)=[N:6][CH:7]=[C:8]([C:10]([F:13])([F:12])[F:11])[CH:9]=1)([O-:3])=[O:2].P(Cl)(Cl)([Cl:17])=O.O>C(#N)C.[Cl-].C([N+](C)(C)C)C1C=CC=CC=1>[Cl:17][C:5]1[C:4]([N+:1]([O-:3])=[O:2])=[CH:9][C:8]([C:10]([F:13])([F:12])[F:11])=[CH:7][N:6]=1

Participants

6

Reactant 3

HCID 962WaterHCID 24813Phosphorus oxychlorideHCID 178526653HCID 178526653, compound

Product 1

HCID 47369502-Chloro-3-nitro-5-(trifluoromethyl)pyridineYield 92%

Reagents, catalysts & solvents 2

HCID 5963Benzyltrimethylammonium chlorideCatalystHCID 6342AcetonitrileSolvent

Procedure

In a 25 ml flask, 3-nitro-5-trifluoromethyl-pyridin-2-ol (300 mg, 1.44 mmol) was dissolved in acetonitrile (4.5 ml), and then phosphorus oxychloride (0.4 ml, 4.33 mmol) and benzyltrimethyl ammonium chloride (164 mg, 0.721 mmol) were added thereto. The mixture was stirred for 3 hours at 800. After completion of the reaction, water was added thereto and the mixture was extracted with ethyl acetate. The combined organic layer was dried over anhydrous sodium sulfate (Na2SO4), filtered and evaporated under reduced pressure to obtain white solid (300 mg, 92%).

Workup

  1. additionwas added
  2. extractionthe mixture was extracted with ethyl acetate
  3. dry with materialThe combined organic layer was dried over anhydrous sodium sulfate (Na2SO4)
  4. filtrationfiltered
  5. customevaporated under reduced pressure

Sources & evidence

ORD record
ord-c94d78fb4d51414eb5351a8269bc40af
Source dataset
uspto-grants-2013_03
Patent number
US08394792B2

Reaction notes

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