Synthesis of ethyl 3-fluoroacrylate from a Tarrant–Stump acetal

Diethyl ketal of 3,3-dibromo-3-fluoropropanal was prepared by UV-initiated condensation of fluorotribromomethane with ethyl vinyl ether, following Tarrant–Stump procedure. Direct oxidation of this acetal to ethyl 3,3-dibromo-3-fluoropropanoate was carried out using Caro’s acid. On treating this ester with triethylamine, dehydrobromination took place, yielding ethyl 3-bromo-3-fluoroacrylate. Finally, a selective reduction of the bromine atom by tributyltin hydride led to ethyl 3-fluoroacrylate.