Polyhalogenonitrobenzenes and derived compounds part 4. Attempted fluorination of 1,2,3,4-tetrachloro-5,6-dinitrobenzene

Article abstract of DOI:10.1016/S0022-1139(96)03507-5

Attempted fluorination of 1,2,3,4-tetrachloro-5,6-dinitrobenzene with potassium fluoride to give 1,2,3,4-tetrafluoro-5,6-dinitrobenzene in DMF or sulpholane, or under solid/liquid phase transfer conditions in toluene using Aliquat 336, TBAI or 18-Crown-6 failed to yield any products resulting from displacement of Cl by F. Rather surprisingly, the two products obtained were pentachloronitrobenzene and pentachlorofluorobenzene.