Sodium Carbonate → 2-[3,5-Bis(1,10-phenanthrolin-2-yl) phenyl]-4,6-diphenyl-1,3,5-triazine

Participants

Reaction Conditions

Reaction Steps

In a stream of argon, 4.26 g of 2-chloro-1,10-phenanthroline, 4.67 g 2-[3,5-bis(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl]-4,6-diphenyl-1,3,5-triazine, 1.06 g of lithium chloride and 767 mg of tetrakis(triphenylphosphine) palladium were suspended in a toluene (200 mL)/ethanol (50 mL) mixed solvent. 33.2 mL of a 2.0 M aqueous sodium carbonate solution was added in the suspension, and the mixture was stirred at 100° C. for 94 hours. Then the reaction mixture was left to be cooled to room temperature and distilled under a reduced pressure to remove low-boiling point ingredients. The obtained residue was purified by alumina column chromatography using a hexane/chloroform (1:2 to 0:1) mixed solvent as a developing solvent, and then recrystallized from a dichloromethane/methanol mixed solvent to give 4.76 g of target 2-[3,5-bis(1,10-phenanthrolin-2-yl)phenyl]-4,6-diphenyl-1,3,5-triazine as a white powder (yield, 86%).

Provenance & Evidence