Triethylamine → HCID 70019004, compound

Participants

Reaction Steps

To 150 ml of N,N-dimethyl formamide (hereinafter abbreviated as “DMF”) were added 7.0 g (27 mmol) of 4-(1,3-dioxolan-2-ylethyl)-2,6-diflurophenyl boronic acid obtained in Step 2, 5.0 g (27 mmol) of 4-bromobenzonitrile, 10 g (99 mmol) of triethyl amine, 0.20 g (0.89 mmol) of palladium acetate and 0.50 g (1.9 mmol) of triphenylphosphine and the mixture was refluxed for 4 hours. The solvent was distilled off under reduced pressure. To the residue of this distillation were added 500 ml of methylene chloride and 250 ml of a 10% aqueous ammonia and the mixture was stirred. The organic layer was dried over magnesium sulfate and the solvent was distilled off under reduced pressure. The residue was purified by column chromatography on silica gel (eluting solvent: toluene/ethyl acetate=5/1) and then the solvent was distilled off under reduced pressure. The residue thus obtained was washed with ethanol and then dried under reduced pressure to afford 4.4 g (14 mmol) of 1-(1,3-dioxolan-2-ylethyl)-3,5-difluoro-4-(4-cyanophenyl)benzene. (Yield: 52%)

Provenance & Evidence