Trifluoroacetic anhydride → HCID 66968567, compound
Reaction equation
[F:1][C:2]1[CH:3]=[C:4]([C:8]2[N:13]=[C:12]([C:14]#[N:15])[CH:11]=[CH:10][C:9]=2[CH3:16])[CH:5]=[CH:6][CH:7]=1.FC(F)(F)C(OC(=O)C(F)(F)F)=[O:20].C([O-])([O-])=O.C([O-])([O-])=O.OO.OO.OO.[Na+].[Na+].[Na+].[Na+].C(=O)([O-])O.[Na+]>C(#N)C.C(OCC)(=O)C>[F:1][C:2]1[CH:3]=[C:4]([C:8]2[C:9]([CH3:16])=[CH:10][CH:11]=[C:12]([C:14]#[N:15])[N+:13]=2[O-:20])[CH:5]=[CH:6][CH:7]=1Participants
Conditions
- Temperature
- 0 °C
Procedure
To a solution (50 mL) of 6-(3-fluorophenyl)-5-methylpyridine-2-carbonitrile (4.42 g, 20.8 mmol) in acetonitrile were added trifluoroacetic acid anhydride (17.6 g, 62.4 mmol) and sodium percarbonate (6.5 g, 41.6 mmol) at 0° C., and the mixture was stirred at 0° C. for 1 hr and at room temperature overnight. The reaction solution was divided into two layers with ethyl acetate and saturated aqueous sodium hydrogen carbonate solution and subjected to extraction (3 times) with ethyl acetate. The organic layer was washed with saturated brine, dried over anhydrous magnesium sulfate and filtered. The disappearance of sodium percarbonate was confirmed, and the solvent was evaporated under reduced pressure. The residue was purified by silica gel chromatography to give the title compound (1.4 g, 29%) as a white solid.
Workup
- extractionsubjected to extraction (3 times) with ethyl acetate
- washThe organic layer was washed with saturated brine
- dry with materialdried over anhydrous magnesium sulfate
- filtrationfiltered
- customthe solvent was evaporated under reduced pressure
- customThe residue was purified by silica gel chromatography
Sources & evidence
- ORD record
- ord-7aee7121c4ef45c5a888ed681a434675
- Source dataset
- uspto-grants-2013_05
- Patent number
- US08445509B2
Reaction notes
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