Bromobenzene → HCID 10266074, compound

Participants

Reaction Steps

A mixture of 13.0 g of 3-methoxyacridan (57.7 mmol), 259 mg of Pd(OAc)2 (1.15 mmol), 187 g of tri-t-butylphosphine (0.92 mmol), 8.32 g of sodium t-butoxide (86.6 mmol), and 10.9 g of bromobenzene (69.2 mmol) in 100 mL of dry toluene was stirred under inert atmosphere at room temperature for 18 h. The reaction mixture was poured into a mixture of 300 mL of CH2Cl2 and 100 g of silica gel. The mixture was filtered, washed with an additional 500 mL of CH2Cl2, and the solids were discarded. The filtrate was concentrated in vacuo to afford a yellow solid. The solid was triturated in 100 mL of hexanes, filtered, washed with an additional 100 mL of hexanes, and dried to afford 13.8 g of N-phenyl-3-methoxyacridan, by NMR analysis (83%).

Provenance & Evidence