Efficient Multigram-Scale Synthesis of 7-Substituted 3-Methyltetral-1-ones and 6-Fluoromenadione

Herein, we report a safe and economical multigram synthesis of 6-fluoromenadione, an intermediate in the novel biologically active agents. The key to this six-step sequence process involves condensation readily available starting 4′-fluoropropiophenone glyoxylic acid, bromination–elimination from 7-fluoro-3-methyltetral-1-one allowing aromatization naphthol intermediate, which is then oxidized into corresponding 6-fluoromenadione. has been demonstrated 25 g material scale with improved overall yield 50% applied five other 7-substituted 3-methyltetralones their 6-substituted menadiones.