Chemistry, Vol 8, No 1 (2015)

Formation of 5-fluoromethylfurfural from 5-halomethylfurfurals catalyzed by crown ethers

Mikhail Yurievich Chernyak, Valery Evgenievich Tarabanko, Andrey Andreevich Morozov, Alexander Alexandrovich Kondrasenko

Abstract


5-fluoromethylfurfural has been obtained by interaction of 5-bromo- and 5-chloromethylfurfurals with potassium bifluoride in the presence of dibenzo-24-crown-8 and 18-crown-6 in acetonitrile medium. The yield attains 40 – 60 mol. %, and the selectivity of 5-bromomethylfurfural conversion is close to 90 %. The NMR and MS spectra are described. The results demonstrate the capability of the KHF2/crown-ethers system to process biomass-derived feedstock molecules to valuable furan compounds by exchange reactions