Acridan → N-(4-nitrophenyl)acridan

Participants

Reaction Steps

A mixture of 10.00 g of acridan (55.2 mmol), 0.26 g of Pd(OAc)2 (0.11 mmol), 0.20 g of tri-t-butylphosphine (0.88 mmol), 7.96 g of sodium t-butoxide (82.8 mmol), and 12.39 g of 1-bromo-4-nitrobenzene (61.3 mmol) in 150 mL of dry toluene (MgSO4) was stirred at room temperature under inert atmosphere for 18 h. The reaction mixture was extracted with 1 L of CH2Cl2 and filtered through silica gel. The filtrate chromatographed on silica gel with 2.5-5% ethyl acetate in hexanes to afford white solid that was triturated in hexanes, filtered and dried to yield 4.00 g (24%) of pure N-(4-nitrophenyl)acridan.

Provenance & Evidence