Dimethyl Ether → 2'-amino-p-terphenyl

Participants

Reaction Steps

2,5-dibromoaniline (50 g, 199.27 mmol, 1.0 equivalent), phenylboronic acid (58.31 g, 478.25 mmol, 2.4 equivalents), tetrakis(triphenylphosphine)palladium(0) (6.91 g, 5.98 mmol, 0.03 equivalent), sodium carbonate (238.48 g), dimethyl ether (750 milliliters), and water (750 milliliters) were loaded, and the mixture was refluxed for 7 hours. After that, the precipitate was separated by filtration and removed, and ethyl acetate was added to the resultant reaction solution so that an organic layer was extracted. The extracted organic layer was washed with a saturated salt solution, dried with anhydrous sodium sulfate, and concentrated. The resultant residue was purified by short column chromatography (methylene chloride) and silica gel chromatography (methylene chloride:hexane=1:1→2:1). An appropriate amount of hexane was added to the purified residue, and the resultant precipitate was separated by filtration. The resultant precipitate was dried, whereby a white solid was obtained (39.4 g, yield: 81%).

Provenance & Evidence