Ethanol → 3-fluoro-4-(3-methyl-1H-1,2,4-triazol-1-yl)benzonitrile

HRID 71131Notes

Reaction equation

Br[C:2]1[CH:7]=[CH:6][C:5]([N:8]2[CH:12]=[N:11][C:10]([CH3:13])=[N:9]2)=[C:4]([F:14])[CH:3]=1.C(=O)([O-])[O-].[K+].[K+].C(O)C.[CH3:24][N:25](C=O)C>O.[Cl-].[Na+].O.[C-]#N.[C-]#N.[C-]#N.[C-]#N.[C-]#N.[C-]#N.O.O.O.[K+].[K+].[K+].[K+].[Fe+2].C([O-])(=O)C.[Pd+2].C([O-])(=O)C>[F:14][C:4]1[CH:3]=[C:2]([CH:7]=[CH:6][C:5]=1[N:8]1[CH:12]=[N:11][C:10]([CH3:13])=[N:9]1)[C:24]#[N:25]

Participants

Conditions

Temperature: 120 °C

Procedure

Under a nitrogen atmosphere, to a mixture of 1-(4-bromo-2-fluorophenyl)-3-methyl-1H-1,2,4-triazole (1.02 g), potassium carbonate (0.55 g) and potassium hexacyanoferrate(II) trihydrate (0.68 g) in DMF (4 mL)/ethanol (0.20 mL) was added palladium acetate (45 mg) at room temperature, and the mixture was stirred at 120° C. for 2 hr. The reaction mixture was allowed to cool to room temperature, and diluted with water and saturated brine, and the mixture was extracted with ethyl acetate. The extract was washed with saturated brine, the organic layer was dried over anhydrous magnesium sulfate, and the solvent was evaporated under reduced pressure. The residue was purified by silica gel column chromatography (ethyl acetate/hexane) to give the title compound (0.51 g).

Workup

temperatureto cool to room temperature
extractionthe mixture was extracted with ethyl acetate
washThe extract was washed with saturated brine
dry with materialthe organic layer was dried over anhydrous magnesium sulfate
customthe solvent was evaporated under reduced pressure
customThe residue was purified by silica gel column chromatography (ethyl acetate/hexane)

Sources & evidence

ORD record: ord-eb635dcdc5b64f4d8c3939c74a9b577a
Source dataset: uspto-grants-2014_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08822699B2

Reaction notes

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