Facile synthesis of 3-(trifluoromethyl)adamantane derivatives

[Display omitted] •An effective synthesis for 1-fluoro-3-(trifluoromethyl)adamantane is proposed.•1-Fluoro-3-(trifluoromethyl)adamantane can be prepared in a multi-gram amount starting from commercially available 3-hydroxyadamantane-1-carboxylic acid.•1-Fluoro-3-(trifluoromethyl)adamantane can be used for preparation of (trifluoromethyl)adamantane derivatives (acids, amines, etc.).•The transformations involving participation of fluorine atom at bridgehead position of adamantane were revealed. A facile synthesis for 1-fluoro-3-(trifluoromethyl)adamantane, based on fluorination of 3-hydroxyadamantane-1-carboxylic acid, was developed. Its synthetic potentialities for preparation of (trifluoromethyl)adamantane derivatives containing diverse functional groups (acids, amines, etc.) in a bridgehead position, were disclosed.