Toluene → 2-[5-(9-Anthryl)-4'-(2-pyridyl)biphenyl-3-yl]-4,6-diphenyl-1,3,5-triazine

Participants

Reaction Steps

In a stream of argon, 0.98 g (3.21 mmol) of 9-(4,4,5,5-tetramethyl-1,3,2-dioxabororan-2-yl)anthracene, 1.50 g (3.21 mmol) of 2-(3,5-dibromophenyl)-4,6-diphenyl-1,3,5-triazine and 37.1 mg (0.032 mmol) of tetrakis(triphenylphosphine)palladium were suspended in a mixed solvent composed of 100 mL of toluene and 20 mL of ethanol, and the resultant suspension was heated to 60° C. To the suspension, 9.63 mL (9.63 mmol) of an aqueous 1M K2CO3 solution was gradually added dropwise, and the mixture was stirred for 3 hours. Then the mixture was cooled to room temperature, and 0.96 g (4.82 mmol) of 4-(2-pyridyl)phenylboronic acid and 6.42 mL (6.42 mmol) of an aqueous 1M K2CO3 solution were added. Then the mixture was heated to 60° C. and maintained at that temperature for 17 hours while being stirred. Then the reaction mixture was cooled to room temperature, and was then distilled under a reduced pressure to remove all volatile materials. Methanol was added to the concentrate, and the thus-deposited solid was collected by filtration. The obtained crude product was purified by silica gel chromatography using a hexane/chloroform (1:2) mixed solvent as an eluent to give 0.68 g of the target 2-[5-(9-anthryl)-4′-(2-pyridyl)biphenyl-3-yl]-4,6-diphenyl-1,3,5-triazine as a white solid (yield: 330).

Provenance & Evidence