Regiospecific synthesis of aromatic compounds via organometallic intermediates. Part 6. 1,3,5-perfluoroalkylether benzenes

Article abstract of DOI:10.1016/0022-1139(95)03307-0

1,2,3-Tribromobenzene can undergo a mono lithium-halogen exchange reaction to yield 3,5-Br2C6H3Li which can subsequently react with a perfluoroalkylether ester, R_fOR_fC(O)OC2H5, yielding the aryl ketone 3,5-Br2C6H3C(O)R_fOR_f.A classical SF4/HF reaction of this ketone yields the perfluoroalkylether benzene, 3,5-Br2C6H3CF2R_fOR_f.This process can be repeated stepwise until all bromines are substituted, yielding the final product 1,3,5-C6H3(CF2R_fOR_f)3.The R_fOR_f was chosen as C3F7O2CF(CF3).Other perfluoroalkyl- and perfluoroalkyl-ether esters or other electrophiles can be chosen to react with the various organolithium intermediates. - Keywords: Regiospecific synthesis; Perfluoroalkylether benzenes; Mass spectrometry; IR spectroscopy