1,8-dibromoanthraquinone → 1,8-Dibromoanthracene

Participants

Reaction Conditions

Reaction Steps

23.6 g (65 mmol) of 1,8-dibromoanthraquinone were suspended in 250 ml of methanol. At 10° C., 9.9 g (260 mmol) of NaBH4 were added slowly and the mixture was subsequently stirred at 0° C. for 2 hours. The mixture was poured onto 800 ml of ice, stirred and filtered under reduced pressure. The solid was subsequently suspended in 400 ml of 18% strength hydrochloric acid and stirred at 70° C. for 5 hours, after which it was once again filtered off under reduced pressure, washed until neutral and dried. The solid was stirred with 14.8 g of NaBH4 in 250 ml of isopropanol at 85° C. (reflux) for 3 hours, brought to a pH of 7 by addition of dilute hydrochloric acid, filtered off with suction and washed with water. 1,8-Dibromoanthracene was obtained in a yield of 16.2 g (74% of theory).

Provenance & Evidence