Benzene → 1-[3-(N-methylamino)phenyl]-4-[3,5-bis(trifluoromethyl)phenyl]-1,3-butadiyne

Participants

Reaction Steps

320 mg of the thus-obtained 1-[3-(N-methylamino)phenyl]-1,3-butadiyne and 700 mg of 3,5-bis(trifluoromethyl) iodobenzene were dissolved in 30 ml of trimethylamine in an atmosphere of argon, and 14 mg of bis(triphenylphosphine)palladium (II) chloride and 4 mg of copper (I) chloride were then rapidly added to the reaction mixture. After the solution had been stirred at room temperature for 13 hours, 50 ml of benzene were added thereto, and the solvent was then evaporated. The residue was neutralized by 1N hydrochloric acid and subjected to extraction with 50 ml of benzene three times. The organic layer was then dried over magnesium sulfate, and the solvent was evaporated. The residue was then purified by silica-gel chromatography using a mixture of hexane and benzene as an eluent to obtain 580 mg of 1-[3-(N-methylamino)phenyl]-4-[3,5-bis(trifluoromethyl)phenyl]-1,3-butadiyne. This compound was a yellowish green crystal having a melting point of from 75° to 76° C.

Provenance & Evidence