Method for aromatic fluorination

Patent metadata

Field	Value
Publication number	US-10654776-B2
Application number	US-201716098296-A
Country	US
Kind code	B2
Filing date	May 2, 2017
Priority date	May 2, 2016
Publication date	May 19, 2020
Grant date	May 19, 2020

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 A 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

The invention claimed is:

1. A fluorination method comprising:
providing an aryl fluorosulfonate having the following structure to a reaction mixture:

wherein Ar is aryl or heteroaryl;
providing a fluorinating reagent to the reaction mixture; and
reacting the aryl fluorosulfonate and the fluorinating reagent to provide a fluorinated aryl species having the following structure:

2. The fluorination method of claim 1 , wherein the solvent is selected from the group consisting of polar aprotic solvents, alkoxy ether solvents, nitrile solvents, and aromatic solvents.

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

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

Assignees

• Dow Global Technologies Llc
• Univ Michigan

Inventors

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

Classifications

• C07D311/16

  substituted in position 7 · CPC title

• C07D213/57

  Nitriles · CPC title

• C07C317/14

  having sulfone or sulfoxide groups bound to carbon atoms of six-membered aromatic rings · CPC title

• C07D213/79

  Acids; Esters · CPC title

• C07J21/008

  at position 17 · CPC title