A convenient synthetic route to 2,4,6-tris(chlorosulfonyl)- and 2,4,6-tris(fluorosulfonyl)phenol, aniline and chlorobenzene

Convenient and preparative synthetic procedures of 2,4,6-tris(chlorosulfonyl)- and 2,4,6-tris(fluorosulfonyl)phenol, -chlorobenzene and -aniline have been elaborated. Chlorine exchange for fluorine by KF interaction on 2,4,6-tris(chlorosulfonyl)aniline and especially 2,4,6-tris(chlorosulfonyl)phenol proceeds easily and selectively under anhydrous conditions in dioxane. Unlike, 2,4,6-tris(chlorosulfonyl)chlorobenzene transformation requires the presence of water. On the basis of 2,4,6-tris(fluorosulfonyl)phenol and some of its salts, XRD measurements demonstrated the structural similarity to picric acid and its derivatives in the solid state.