Diphenylamine → 9,9-Dimethoxyethyl-2-diphenylaminofluorene

Participants

Reaction Steps

In a round-bottom flask, a mixture of 2-bromo-9,9-dimethoxyethylfluorene (2.0 g, 5.54 mmol), diphenylamine (1.12 g, 6.65 mmol), tris(dibenzylideneacetone)dipalladium (0) (0.012 g, 0.25 mmol %), rac-BINAP (0.025 g, 0.75 mmol %), and sodium t-butoxide (0.74 g, 7.76 mmol) in dry toluene (100 ml ) was placed and heated at the refluxing temperature of the solvent for 16 h under an atmospheric pressure of nitrogen. After cooling the reaction mixture to room temperature, it was diluted with diethylether (60 ml), washed with brine (40 ml) and water. Organic layer was dried over sodium sulfate and concentrated in vacuuo. The crude product was purified by preparative thin layer chromatography (silica gel, Rf=0.3 using hexane-EtOAc-toluene/1:1:3 as eluent) to give 9,9-dimethoxyethyl-2-diphenylaminofluorene (1.6 g).

Provenance & Evidence