Ring fluorination of non-activated aromatic compounds
AssigneeAir Products and Chemicals, Inc.
InventorsRonald Eric. Banks, Mohamed Khalifa Besheesh
Life of this patent
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Abstract
Aromatic compounds having one or more electron-withdrawing substituents are fluorinated, preferably in a nitromethane solvent, by contact with tri(halo- or trifluoromethyl) substituted N-fluorotriazinium salts of the following Formula I: wherein three A moieties are independently CR, where each R is independently halogen or trifluoromethyl; two A moieties are independently Z, where each Z is independently nitrogen or a quaternary nitrogen atom and Y is a counterion or group of counterions which are inert to chemical attack by fluorine. Preferably the cation of the salt is 2,4,6-trichloro-1,3,5-triazinium.
Claims22
A method of fluorinating a substrate selected from the group consisting of aromatic compounds having one or more electron-withdrawing substituents which comprises contacting the substrate with a tri(halo- or trifluoromethyl) substituted N-fluorotriazinium salt of the following Formula I:
- wherein
- three A moieties are independently CR, where each R is independently halogen or trifluoromethyl;
- two A moietios are independently Z, where each Z is independently nitrogen or a quaternary nitrogen atom;
- and
- Y− is a counterion or group of counterions which are inert to chemical attack by fluorine.
A method of fluorinating a substrate selected from the group consisting of unsubstituted aromatic compounds and aromatic compounds having one or more electron-withdrawing substituents which comprises contacting the substrate with a tri(halo- or trifluoromethyl) substituted N-fluorotriazinium salt of the following Formula I:
- wherein:
- three A moieties are independently CR, where each R is independently halogen or trifluoromethyl;
- two A moieties are independently Z, where each Z is independently nitrogen or a quaternary nitrogen atom;
- and
- Y− is a counterion or group of counterions which are inert to chemical attack by fluorine;
- wherein each R is trifluoromethyl.
A method or fluorinating a substrate selected from the group consisting of unsubstituted aromatic compounds and aromatic compounds having one or more electron-withdrawing substituents which comprises contacting the substrate with a N-fluoro-2,4,6-tris(trifluoromethyl)-1,3,5-triazinium compound of the following Formula IIC:
- wherein Y− is a counterion or group of counterions which are inert to chemical attack by fluorine.
A method of fluorinating a substrate selected from the group consisting of aromatic compounds having one or more electron-withdrawing substituents which comprises contacting the substrate with a N-fluoro-1,3,5-triazinium compound of the following Formula II:
- wherein:
- R1, R2, and R3 are selected from the group consisting of chlorine, fluorine and trifluoromethyl and
- Y− is selected from the group consisting of fluoride, fluorosulfate, alkanesulfonate, alkyl sulfate, perfluoroalkanesulfonate, arenesulfonate, alkanecarboxylate, perfluoroalkanecarboxylate, tetrafluoroborate, tetraphenylborate, hexafluorophosphate, hexafluoroantimonate, hexafluoroarsenate, chlorate, sulfate (=2Y−), hydrogen sulfate and F(HF)x− where x is at least 1.
Dependencies are inferred from the claim text.