Abstract A library of 7-acetyl-2-adamantyl-5-bromo-6-methoxybenzo[b]furans 2a–c was synthesized and converted to the corresponding ortho-(hydroxyacetyl)-substituted 2-adamantyl-benzo[b]furan derivatives 3a–c. Adamantane derivatives (1-ethynyladamantane, 1-(4-ethynylphenyl)adamantane, and 2-(prop-2-yn-1-yl)adamantane) were used as terminal alkynes in the Sonogashira reaction. The structures of both series of compounds were characterized using a combination of spectroscopic methods.