We synthesized 4-(l-adamantyl)phenol (llI) [3] and 4-(l-adamantyl)resorcinol (IV) by refluxing l-bromoadamantane with phenol or resorcinol in benzene until the evolution of hydrogen bromide ceased. We were able to get both the mono and dibromo derivatives by bromination of (III), depending on the reaction conditions. 2,6-Dibromo-4-(l-adamantyl)phenol (V) was formed in 89.3% yield when III was treated with bromine in a mixture of methanol and acetic anhydride. We got the same compound when the reaction was carried out in carbon tetrachloride or glacial acetic acid, though the yield was slightly lower, 83% and 75%, respectively. We used a milder brominating agent, dioxane dibromide in ether, to prepare 2-bromo4-(l-adamantyl)phenol (VI). In regard to the iodo derivatives, 2-iodo-4-(!-adamantyl)phenol (VII) was readily formed by treatment of III with iodine monoch!oride in glacial acetic acid. The yield of VII was 93%. We turned to a stronger iodinating agent, iodine in morpholine, to introduce a second iodine atom, but were unable to get the desired compound, isolating only the monoiodo derivative VII in lower yield, 50%.