Congressane → 4,9-Dibromodiamantane

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Diamantane (50 g, 0.26 mol) was added over 1 h to bromine (200 mL) at 0° C. Aluminum bromide (5.4 g, 0.02 mol) was added and the mixture was stirred at 0° C. for 3 h and at ambient temperature for 16 h. When glc showed less than 5% monobrominated diamantanes, the bromine was removed under reduced pressure and the residue was triturated with pentane (300 mL). The precipitate was filtered, and was washed with pentane (2×150 mL) and methanol (3×100 mL). The residue was recrystallized from toluene to give 45 g (50%) of 4,9-dibromodiamantane, a white solid: mp 328° C. (lit. mp 324°-326° C.); 1H NMR (CDCl3) δ1.97 (s, 6H) 2.31 (s, 12H); 13C NMR (CDCl3) δ39.64, 48.45, 62.81.

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