Dichloromethane → HCID 86583805, compound

Participants

Reaction Steps

A mixture of 10.00 g of acridan (55.2 mmol), 247.7 mg of Pd(OAc)2 (1.10 mmol), 178.6 mg of tri-t-butylphosphine (0.88 mmol), 7.95 g of sodium t-butoxide (82.7 mmol), and 17.06 g of 1-bromopyrene (60.7 mmol) in 100 mL of dry toluene was allowed to stir under inert atmosphere. The exothermic reaction heated to reflux, causing a precipitate to form. An additional 200 mL of toluene was added to the mixture and stirring was continued at room temperature for 1 h. The reaction mixture was poured into a mixture of 600 mL of CH2Cl2 and 100 g of silica gel. The mixture was filtered, and the solid material was washed with 600 mL of CH2Cl2. The filtrate was concentrated in vacuo to afford a thick liquid containing a precipitate. The precipitate was collected by filtration, washed with 300 mL of toluene and 500 mL of hexanes, and dried to afford 12.69 g of N-pyrenylacridan by 1H-NMR analysis. The mother liquor was concentrated to a yellow solid which was triturated in 300 mL of hexanes for 30 min. The precipitate was collected by filtration, washed with 200 mL of hexanes and dried to afford 7.46 g of solid. 1H-NMR analysis showed the second crop of product was slightly less pure than the first. The two lots were combined to afford 20.15 g of the N-pyrenylacridan (95.7%).

Provenance & Evidence