Dow Agrosciences LLC

University of Michigan

Dow Global Technolgoies LLC

Corteva Agriscience LLC

Douglas Bland

Melanie S Sanford

Gary A Roth

Patrick S Hanley

Sydonie D Schimler

Megan A Cismesia

Ronald Ross, Jr

James R McConnell

Peter Lee Johnson

Timothy Calvin Johnson

David E Podhorez

Yang Cheng

Christopher Thomas Hamilton

Laura Allen

James M Renga

Kim Eric Arndt

Joseck M Muhuhi

Timothy J Adaway

George J Frycek

Alexander P Fung

Jason S Fisk

Craig Bott

Sarah Ryan

Shin Hee Lee

Joseph C Neuman

Clark S Davis

James Mcconnell

Melanie Sanford

Patrick S Hanly

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 SOFto a reaction mixture; reacting the SOFand the ammonium salt to provide a fluorinated aryl species. Further disclosed a fluorination method comprising providing a compound having the structure Ar&#x2014;OH to a reaction mixture; where Ar is an aryl or heteroaryl; providing SOFto the reaction mixture; providing a fluorinating reagent to the reaction mixture; reacting the SOF, the fluorinating reagent and the compound having the structure Ar&#x2014;OH to provide a fluorinated aryl species having the structure Ar&#x2014;F.

Method for aromatic fluorination

Disclosed is a fluorination method comprising providing a fluorinating reagent and a solvent to a reaction mixture; providing a compound having the formula Ar&#x2014;X to the reaction mixture; wherein Ar is aryl, substituted aryl, heteroaryl or substituted heteroaryl, and X is Cl, Br, I or NO, providing tetramethylammonium 2,6-dimethylphenolate to the reaction mixture; and reacting under conditions sufficient to provide a species having the formula Ar&#x2014;F.

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 SOFto a reaction mixture; reacting the SOFand the ammonium salt to provide a fluorinated aryl species. Further disclosed a fluorination method comprising providing a compound having the structure Ar&#x2014;OH to a reaction mixture; where A is an aryl or heteroaryl; providing SOFto the reaction mixture; providing a fluorinating reagent to the reaction mixture; reacting the SOF, the fluorinating reagent and the compound having the structure Ar&#x2014;OH to provide a fluorinated aryl species having the structure Ar&#x2014;F.

Methods of preparing a fluorinated aryl or heteroaryl substrate by combining a quaternary ammonium cyanide and an aryl or heteroaryl substrate substituted with at least one chloro, bromo, sulfonyl, or nitro group to thereby provide a mixture, and combining the mixture with hexafluorobenzene to thereby provide the fluorinated substrate.

Process for fluorinating compounds

Disclosed are mild temperature (e.g., from 0 to 80&#xb0; C.) SAr fluorinations of a variety of halide and sulfonate substituted aryl and heteroaryl substrates using NMeF.

Methods of preparing a fluorinated substrate by combining potassium fluoride, a quaternary ammonium salt, and a substrate substituted with at least one chloro, bromo, sulfonyl, or nitro group to thereby provide the fluorinated substrate are disclosed.

5-Substituted-8-alkoxy[1,2,4]triazolo[1,5-c]pyrimidin-2-amines are manufactured from 4-amino-2,5-dialkoxypyrimidines in an improved process in which the generation of gaseous by-products is controlled by the continuous addition of hydroxylamine as a free base.

Process for the preparation of 2-amino-5,8-dimethoxy[1,2,4]triazolo[1,5-c]pyrimidine from 4-amino-2,5-dimethoxypyrimidine

2-Amino-5,8-dialkoxy[1,2,4]-triazolo[1,5-c]pyrimidines are manufactured from 4-chloro-2,5-dialkoxypyrimidines in a process that avoids hydrazine and cyanogen halide.

Process for the preparation of 2-amino-5,8-dimethoxy[1,2,4]triazolo[1,5-c]pyrimidine from 4-chloro-2,5-dimethoxypyrimidine

In one form, processes for the production of certain N-substituted sulfoximine N-oxides are provided. Further embodiments, forms, objects, features, advantages, aspects, and benefits shall become apparent from the description.

Processes for the production of N-substituted sulfoximine pyridine N-oxides

Provided herein are processes for the preparation of alkoxycarbonyl isothiocyanates from alkyl chloroformates and thiocyanates in toluene by controlling the amounts of water and catalyst.

Process for preparing alkoxycarbonyl isothiocyanate

In one embodiment, processes for the preparation of certain functionalized pyridine N-oxides are provided. In one form, the functionalized pyridine N-oxides include 2-substituted-5-(1-alkylthio)alkyl-pyridine N-oxides. Further embodiments, forms, objects, features, advantages, aspects, and benefits shall become apparent from the description.

Functionalized pyridine N-oxides and processes for the preparation of the same

3-substituted-6-trifluoromethyl pyridines are useful synthetic intermediates in the preparation of the N-substituted (6-haloalkylpyridin-3-yl)alkyl sulfoximines, which are useful in forming potent insecticides. Methods of forming such 3-substituted-6-trifluoromethyl pyridines are disclosed. Also disclosed are methods of using 6-trichloromethyl halogenated pyridines to form 3-substituted-6-trifluoromethyl pyridines are disclosed.

Methods for preparing 3-substituted-6-trifluoromethyl pyridines and methods for using 6-trichloromethyl halogenated pyridines

2-Trifluoromethyl-5-(1-substituted)alkylpyridines of formula (I)    

Process for the preparation of 2-trifluoromethyl-5-(1-substituted)alkylpyridines

Cyano-substituted sulfilimines and sulfoximines are produced efficiently and in high yield from the corresponding sulfides by reaction with cyanamide and hypochlorite.

Growing community of inventors

Midland, MI, United States of America

Douglas Bland