104224-68-2

White powder

2-(Adamantan-1-yl)-4-bromophenol is an intermediate in the synthesis of Adapalene (A225000), a retinoid selective for retinoic acid receptor (RAR) subtypes β and γ; an antiacne agent.

Preparation of 2-(1-adamantyl)-4-bromophenol (III): 4-bromophenol (10.0 g, 57.8 mmol) was dissolved in methanesulfonic acid (15 mL) with 1-adamantanol (8.78 g, 57.76 mmol), and the reaction was stirred for 3 hr at 70 °C. After completion of the reaction, the mixture was cooled to room temperature and diluted with deionized water (50 mL). The precipitated white solid was collected by filtration, washed several times with deionized water and subsequently dried to afford the target product 2-(1-adamantyl)-4-bromophenol (III). [Yield: 17 g, Yield: 97%]

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