Hydrochloric Acid → 2-Bromo-9,10-di(naphthalen-1-yl)anthracene

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Reaction Steps

360 g (1.74 mol) of bromonaphthalene was dissolved with THF in a 5 L flask and the temperature was lowered to −78° C. and 1600 ml (1.6 mol) of 1.6M n-BuLi was slowly added dropwise thereto. The mixture was stirred for one hour, and then 200 g (0.68 mol) of 2-bromoanthraquinone was added thereto in a solid state and then the temperature was slowly raised to room temperature and the resultant mixture was stirred. After 12 hours, 500 ml of 2N HCl(aq) was added thereto. Then, an organic layer was isolated and dried over MgSO4 and condensed under reduced pressure, thereby producing Compound C. The Compound C was used in the subsequent reaction without purification. Compound C, 346 g (2.09 mol) of KI, and 443 g (4.1 mol) of NaH2PO2.H2O were diluted with an acetic acid and then the mixture was refluxed while heating. The temperature was lowered to room temperature and thus a solid was precipitated. The solid was filtered, washed with excess water and MeOH, and re-crystallized with 300 ml of toluene, thereby producing 2-bromo-9,10-di(2-naphthyl)anthracene (230 g, 64%).

Provenance & Evidence