Anthraquinone → HCID 22138029, compound

Participants

Reaction Steps

Under an atmosphere of argon, 1-(3-bromophenyl)naphthalene (6.5 g, 20 mmole, 2.8 eq) was dissolved into a mixed solvent composed of anhydrous toluene (25 ml) and anhydrous THF (25 ml) and the resultant solution was cooled at −25° C. in a dry ice/methanol bath. To the cooled solution, a hexane solution of n-butyllithium (1.50 mole/liter, 15 ml, 23 mmole, 1.1 eq) was added and the resultant solution was stirred at −20° C. for 1 hour. To the obtained mixture, anthraquinone (1.5 g, 7.2 mmole) was added and the resultant mixture was stirred at −20° C. for 1 hour and at the room temperature for 3 hours and left standing for one night. To the obtained reaction mixture, a saturated aqueous solution of ammonium chloride (20 ml) was added. The formed solid was separated by filtration and washed with water, methanol and acetone and a white solid (5.9 g, quant.) was obtained.

Provenance & Evidence