Ammonium Chloride → 6-Fluoro-4-(trifluoromethyl)pyridine-2-carbonitrile

HRID 1880719Notes

Reaction equation

HRID 1880719 reaction equation
Cl[C:2]1[CH:7]=[C:6]([C:8]([F:11])([F:10])[F:9])[CH:5]=[C:4]([C:12]#[N:13])[N:3]=1.[F-:14].[K+].[Cl-].[NH4+]>CS(C)=O>[F:14][C:2]1[N:3]=[C:4]([C:12]#[N:13])[CH:5]=[C:6]([C:8]([F:11])([F:10])[F:9])[CH:7]=1

Participants

5

Reactant 3

HCID 25517Ammonium ChlorideHCID 522689Potassium FluorideHCID 595703326-Chloro-4-(trifluoromethyl)pyridine-2-carbonitrile

Product 1

HCID 534388006-Fluoro-4-(trifluoromethyl)pyridine-2-carbonitrileYield 84.5%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Conditions

Temperature
120 °C

Procedure

To 9 ml of dimethyl sulfoxide were added 0.9 g of 2-chloro-6-cyano-4-trifluoromethylpyridine, and 0.76 g of potassium fluoride, and the mixture was stirred at 120° C. for 2 hours and 30 minutes. Thereafter, the reaction solution was allowed to cool to room temperature, and poured into an aqueous saturated ammonium chloride solution, followed by extraction with tert-butyl=methyl=ether three times. The organic layers were combined, washed with an aqueous saturated sodium chloride solution, dried with anhydrous magnesium sulfate, and concentrated. The residue was subjected to silica gel column chromatography to obtain 0.7 g of 6-fluoro-4-trifluoromethylpyridine-2-carbonitrile.

Workup

  1. temperatureto cool to room temperature
  2. extractionfollowed by extraction with tert-butyl=methyl=ether three times
  3. washwashed with an aqueous saturated sodium chloride solution
  4. dry with materialdried with anhydrous magnesium sulfate
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-63b0446c35f54cbfbbd828579797f49c
Source dataset
uspto-grants-2012_11
Patent number
US08318776B2

Reaction notes

Loading…