Aniline → N,N,N'-triphenyl-4-phenylenediamine

Participants

Reaction Conditions

Reaction Steps

0.56 g (6 mmol) of 4-bromotriphenylamine, 0.35 g (0.6 mmol) of bis(dibenzylideneacetone)palladium(0), and 0.58 g (6 mmol) of sodium-tert-butoxide were put into a 100 mL three neck flask, and 5 mL of toluene was added thereto. After nitrogen was substituted for the content of the flask, 0.56 g (6 mmol) of aniline and 0.37 mL (1.8 mmol) of a hexane solution (10 wt %) of tri-tert-butylphosphine were added. This mixture was stirred for 5 hours at 80° C. to be reacted. After the reaction, the reaction was completed by adding a saturated saline solution to the reaction mixture, and an aqueous layer was extracted by approximately 100 mL of ethyl acetate to be separated from an organic layer. The organic layer was dried with magnesium sulfate and filtered. A solid that was obtained by concentrating the filtrate was purified by silica column chromatography, whereby 0.24 g of a light yellow powder solid of DPA that is an object was obtained in the yield of 42% (Synthesis Scheme (i-2)). For the column purification, a mixed solvent of ethyl acetate:hexane=1:20 was used as a developing solvent.

Provenance & Evidence