Benzaldehyde → 2,4-Bis(isopropenyl)dibenzo[b,d]furan-3-amine

Participants

Reaction Steps

A mixture of 2,4-dibromodibenzo[b,d]furan-3-amine (14.5 g, 42.5 mmol), benzaldehyde (4.96 g, 46.8 mmol), 4,4,5,5-tetramethyl-2-(prop-1-en-2-yl)-1,3,2-dioxaborolane (21.44 g, 128 mmol), and potassium phosphate (45.1 g, 213 mmol) in 250 mL of toluene and 25 mL of H2O was bubbled with N2 for 20 minutes. Dicyclohexyl(2′,6′-dimethoxybiphenyl-2-yl)phosphine (0.698 g, 1.701 mmol) and Pd2(dba)3 (0.389 g, 0.425 mmol) were then added, and the mixture was heated to reflux under N2 for 14 h. GC-MS indicated the reaction was done. After cooled to room temperature, the toluene layer was decanted. The aqueous layer was washed with toluene, and the organic layers were combined. 60 mL of concentrated HCl was added. The mixture was stirred at room temperature for 1 h. The precipitated was collected by filtration. The solid was dissolved in dichloromethane and neutralized with NaOH and dried over magnesium sulfate. After solvent evaporation, the residue was purified by column chromatography using 5-10% of ethyl acetate/hexanes as solvent. 6.6 g (59% yield) of product was obtained after purification.

Provenance & Evidence