m-Toluidine → 1292285-22-3

Participants

Reaction Steps

In a 200 mL three-neck flask were placed 3.2 g (8.1 mmol) of 9-(3-bromophenyl)-9-phenylfluorene and 2.3 g (24.1 mmol) of sodium tert-butoxide. The air in the flask was replaced with nitrogen. To this mixture were added 40.0 mL of toluene, 0.9 mL (8.3 mmol) of m-toluidine, and 0.2 mL of a 10% hexane solution of tri(tert-butyl)phosphine. The temperature of this mixture was set to 60° C., 44.5 mg (0.1 mmol) of bis(dibenzylideneacetone)palladium(0) was added to the mixture, and the temperature of this mixture was set to 80° C.; followed by stirring for 2.0 hours. After the stirring, the mixture was subjected to suction filtration through Florisil, Celite, and alumina to give a filtrate. The obtained filtrate was concentrated to give a solid, which was then purified by silica gel column chromatography (the developing solvent has a 1:1 ratio of hexane to toluene) and recrystallized from a mixed solvent of toluene and hexane. Accordingly, 2.8 g of a target white solid was obtained in a yield of 82%. The synthesis scheme of Step 1 is illustrated in (C-1) below.

Provenance & Evidence