IP Library Granted Patent US 10,654,776
Granted Patent B2
US 10,654,776 · App. 16/098,296 · Granted May 19, 2020

Method for aromatic fluorination

Inventors: Melanie S. Sanford (Ann Arbor, MI); Douglas Bland (Midland, MI); Patrick S. Hanley (Midland, MI); Megan A. Cismesia (Midland, MI); Sydonie D. Schimler (Ann Arbor, MI)
Assignee: Dow Global Technologies LLC
C07C17/02C07C17/093C07C25/13C07C41/22C07C45/63C07C67/307C07C201/12C07C231/12C07C253/30C07C317/14C07D209/08C07D209/88C07D213/57C07D213/61C07D213/75C07D213/79C07D215/18C07D279/16C07D311/16C07D453/02C07J21/008
View Patent ↗
Loading inventors, assignments & file history…
Monitor This Case
Get email alerts when status or documents change.
Order Certified Copies
Most orders are placed with the USPTO same day — all within 24 business hours.
Order via The Patent Place →
Pre-filled with this patent's details
Quick Facts
Patent No.
US 10,654,776
App. No.
16/098,296
Granted
May 19, 2020
Kind
B2
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 SO 2 F 2 to a reaction mixture; reacting the SO 2 F 2 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 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.

Claims (8)

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.

Assignments (4)
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Nov 18, 2024
From: DOW GLOBAL TECHNOLOGIES LLC
To: DOW AGROSCIENCES LLC
Reel/Frame 069296/0120 →
CHANGE OF NAME Recorded Nov 18, 2024
From: DOW AGROSCIENCES LLC
To: CORTEVA AGRISCIENCE LLC
Reel/Frame 069383/0319 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Sep 17, 2019
From: BLAND, DOUGLAS; HANLEY, PATRICK S.
To: DOW GLOBAL TECHNOLOGIES LLC
Reel/Frame 050403/0137 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Sep 17, 2019
From: SANFORD, MELANIE S.; CISMESIA, MEGAN A.; SCHIMLER, SYDONIE D.
To: REGENTS OF THE UNIVERSITY OF MICHIGAN
Reel/Frame 050403/0282 →
Continuity (5)
Provisional Application 62330311 · May 2, 2016
Provisional Application 62362721 · Jul 15, 2016
Provisional Application 62376967 · Aug 19, 2016
Provisional Application 62408270 · Oct 14, 2016
Related Publication 20190202758A1 · Jul 4, 2019