Method for aromatic fluorination

Patent metadata

Field	Value
Publication number	US-11230517-B2
Application number	US-202017015775-A
Country	US
Kind code	B2
Filing date	Sep 9, 2020
Priority date	May 2, 2016
Publication date	Jan 25, 2022
Grant date	Jan 25, 2022

Abstract

Disclosed is a fluorination method comprising providing an aryl fluorosulfonate and a fluorinating reagent to a reaction mixture; and reacting the aryl fluorosulfonate and the fluorinating reagent to provide a fluorinated aryl species.Also disclosed is a fluorination method comprising providing, a salt comprising a cation and an aryloxylate, and SO2F2 to a reaction mixture; reacting the SO2F2 and the ammonium salt to provide a fluorinated aryl species.Further disclosed a fluorination method comprising providing a compound having the structure Ar—OH to a reaction mixture; where Ar is an aryl or heteroaryl; providing SO2F2 to the reaction mixture; providing a fluorinating reagent to the reaction mixture; reacting the SO2F2, the fluorinating reagent and the compound having the structure Ar—OH to provide a fluorinated aryl species having the structure Ar—F.

First claim

What is claimed is:

1. A fluorination method comprising:
providing a compound having the structure Ar—OH to a reaction mixture;
where Ar is an aryl or heteroaryl;

providing SO 2 F 2 to the reaction mixture;
providing a fluorinating reagent to the reaction mixture;
reacting the SO 2 F 2 , the fluorinating reagent and the compound having the structure Ar—OH to provide a fluorinated aryl species having the structure Ar—F.

2. The fluorination method of claim 1 , wherein the fluorinating reagent is selected from the group consisting of sodium fluoride, potassium fluoride, cesium fluoride, tetrabutylammonium fluoride, and tetramethylammonium fluoride.

3. A method according to claim 1 , further comprising providing a solvent to the reaction mixture.

4. The fluorination method of claim 3 , wherein the solvent is selected from the group consisting of polar aprotic solvents, alkoxy ether solvents, nitrile solvents, aromatic solvents, and mixtures thereof.

5. The fluorination method of claim 4 , wherein the solvent comprises a polar aprotic solvent.

6. The fluorination method of claim 4 , wherein the solvent comprises an alkoxy ether solvent.

7. The fluorination method of claim 4 , wherein the solvent comprises a nitrile solvents.

8. The fluorination method of claim 4 , wherein the solvent comprises an aromatic solvent.

9. The fluorination method of claim 3 , wherein the fluorinating reagent is selected from the group consisting of sodium fluoride, potassium fluoride, cesium fluoride, tetrabutylammonium fluoride, and tetramethylammonium fluoride.

10. The fluorination method of claim 4 , wherein the fluorinating reagent is selected from the group consisting of sodium fluoride, potassium fluoride, cesium fluoride, tetrabutylammonium fluoride, and tetramethylammonium fluoride.

11. A method according to claim 1 , wherein Ar—OH is

Assignees

• Dow Global Technologies Llc
• Univ Michigan Regents

Inventors

• Sanford Melanie S
• Bland Douglas
• Hanley Patrick S
• Cismesia Megan A
• Schimler Sydonie D

Classifications

• C07C67/307 Primary

  by introduction of halogen; by substitution of halogen atoms by other halogen atoms · CPC title

• C07D209/08

  with only hydrogen atoms or radicals containing only hydrogen and carbon atoms, directly attached to carbon atoms of the hetero ring · CPC title

• C07D209/88

  with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to carbon atoms of the ring system · CPC title

• C07J21/008

  at position 17 · CPC title

• C07C255/50

  to carbon atoms of non-condensed six-membered aromatic rings · CPC title