N-Methylethylenediamine → HCID 54805899, compound

Participants

Reaction Steps

In a 100 mL round-bottom flask tris(dibenzylideneacetone)dipalladium(0) (Pd2(dba)3) (110 mg, 0.120 mmol) and (±)-2,2′-Bis(diphenylphosphino)-1,1′-binaphthalene ((±)-BINAP) (230 mg, 0.37 mmol) were added to 25 mL toluene and stirred for 20 minutes. Next, 2-bromomesitylene (2.45 g, 12.3 mmol), N-methylethylenediamine (1.01 g, 13.6 mmol) and sodium t-butoxide (NaOtBu) (3.56 g, 37 mmol) were added along with 25 mL toluene. This was stirred for 72 hours at 80° C. The flask was then removed from heat, cooled to room temperature and diluted with 20 mL diethyl ether. The solution was then washed with 5×30 mL water and 3×15 mL brine, and dried over magnesium sulfate. After filtering and vacuum removal of solvent, a dark red oil was recovered and used without further purification.

Provenance & Evidence