Various synthetic approaches to fluoroalkyl p-nitrophenyl ethers

Article abstract of DOI:10.1016/S0022-1139(96)03490-2

Homologous 1H,1H-perfluoroalkyl p-nitrophenyl ethers (alkyl = C₂-C₈) were synthesized using different methods. The results are discussed in context with contradictory comments of the literature. The fluoroalkoxylation of p-chloronitrobenzene occurs in only one step, but it is limited to small fluoroalkyl groups. The fluoroalkylation of p-nitrophenol via sulphonic acid esters is a better synthetic route. Differences in reactivity and yield between tosylates, mesylates and inflates are found and discussed. The preferred synthesis includes the use of trifluoromethane sulphonic acid esters.