Potassium Phosphate, Tribasic → N-(1,3-di(prop-1-en-2-yl)dibenzo[b,d]furan-4-yl)acetamide

Participants

Reaction Steps

N-(1,3-dibromodibenzo[b,d]furan-4-yl)acetamide (55 g, 144 mmol), 4,4,5,5-tetramethyl-2-(prop-1-en-2-yl)-1,3,2-dioxaborolane (72.4 g, 431 mmol) and potassium phosphate tribasic (132 g, 574 mmol) were mixed into toluene (800 mL) and water (80 mL). The mixture was bubbled with nitrogen for 20 minutes. Then Pd2(dba)3 (2.63 g, 2.87 mmol) and dicyclohexyl(2′,6′-dimethoxybiphenyl-2-yl)phosphine (4.72 g, 11.49 mmol) were added into the reaction mixture. After bubbled by nitrogen for another 20 minutes, the reaction was refluxed overnight under nitrogen. After cooled to room temperature, the organic layer was washed by water, dried over sodium sulfate and concentrated. After silica gel column (30%-50% EtOAc in hexane) got N-(1,3-di(prop-1-en-2-yl)dibenzo[b,d]furan-4-yl)acetamide (32.5 g, 74.1% yield) as brown solid.

Provenance & Evidence