The bromination of 2-(2-hydroxyhexafluoro)isopropyl-5-methylfuran at the methyl group and subsequent reaction with nitrogen nucleophiles gave some secondary amines and quaternary salts.

2-(2-Hydroxyhexafluoro)isopropyl-5-methylfuran (I), which is readily available by the reaction of cr with hexafluoroacetone [1] is an extremely attractive reagent for synthetic studies in light of its polyfunctional nature. In previous work [2], we showed that nucleophilic substitution of the OH group in furan I proceeds only with difficulty. The hydrogen atom in this group, on the other hand, displays pronounced acidity upon reactions with metals, amines, and alkali solutions. The alcoholates have tow activity in alkylation and acylation reactions [2]. In the present work, we studied the synthetic possibilities of furan I due to the presence of a labile hydrogen atom in the methyl group. This hydrogen atom may be readily replaced by bromine upon treatment with N-bromosuccinimide. In turn, bromide II forms the corresponding salts III-XX with a series of aromatic and heterocyclic amines (Table 1).