Aniline → N-phenyl-2-Dibenzofuranamine

Participants

Reaction Steps

4-bromodibenzo[b,d]furan (3.0 g, 12.1 mmol) and aniline (1.69 g, 18.1 mmol) were mixed in 100 mL of toluene. The solution was bubbled with nitrogen for 15 min. Pd2(dba)3 (0.05 g, 0.05 mmol), 2,2′-bis(diphenylphosphino)-1,1′-binaphthyl (0.15 g, 0.24 mmol) and sodium t-butoxide (1.7 g, 17.4 mmol) were added. The mixture was refluxed overnight under nitrogen. After cooling, the reaction mixture was filtered through celite/silica pad and the filtrate was concentrated under vacuum. The residue was then purified by column chromatography using DCM:hexane (1:1, v/v) as the eluent. 2.0 g (65%) of a white solid was obtained as the product.

Provenance & Evidence