1-(5-Bromo-2-methoxyphenyl)adamantane → 6-[3-(1-Adamantyl)-4-methoxyphenyl]-2-bromonaphthalene

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Reaction Steps

t-BuLi (159 μl, 1.4 M, 0.22 mmol) was added, dropwise, onto a mixture of 3-(1-adamantyl)-1-bromo-4-methoxybenzene (50 mg, 0.16 mmol) and anh. THF (1 ml) under atmosphere of Ar and at −78° C., and the mixture was kept in stirring for 1 hour. After this time, the reaction was allowed to evolve at room temperature, a solution of ZnCl2 (21 mg, 0.16 mmol) in anhydrous THF (0.4 mL) was added and was stirred for 1 more hour. Next, a solution of 6-bromonaphthalenyl trifluoromethanesulphonate (40 mg, 0.13 mmol), Pd(PPh3)4 (9 mg, 0.008 mmol) and anh. THF (0.2 ml) was added and the reaction was kept at room temperature for 16 h. Finally, the reaction was neutralized with HCl (1 M) and extractions with Et2O (3×2 ml) were carried out. The organic phase was washed with sat NaCl (3×3 ml) and H2O (3×3 ml), was dried with MgSO4 and was evaporated to dryness. A crude (58 mg) in form of a yellow solid was obtained, which was recrystallized with the minimum volume of toluene at reflux (0.2 ml), giving the title compound (20 mg, 29%) as a pale yellow powder. The spectroscopic data coincide with those of the Example 4.

Provenance & Evidence