Catherine A Menning

US Patent:

20130172567, Jul 4, 2013

Filed:

Dec 28, 2012

Appl. No.:

13/729580

Inventors:

Dow AgroSciences LLC - indianapolis IN, US
Catherine A. Menning - Midland MI, US
Daniel R. Henton - Midland MI, US

Assignee:

DOW AGROSCIENCES LLC - indianapolis IN

International Classification:

C07F 5/02

US Classification:

546323, 562 7

Abstract:

Methods of isolating a 4-chloro-2-fluoro-3-substituted-phenylboronate include adding carbon dioxide gas or carbon dioxide solid (dry ice) to a solution comprising a 4-chloro-2-fluoro-3-substituted-phenylboronate, an inert organic solvent, and at least one lithium salt to react the at least one lithium salt with the carbon dioxide gas or carbon dioxide solid (dry ice) and form a mixture comprising the 4-chloro-2-fluoro-3-substituted-phenylboronate, the inert organic solvent, and a precipitated solid. The precipitated solid may be removed from the mixture. Methods of using 4-chloro-2-fluoro-3-substituted-phenylboronates to produce methyl-4-amino-3-chloro-6-(4-chloro-2-fluoro-3-substituted-phenyl)pyridine-2-carboxylates are also disclosed. A 4-chloro-2-fluoro-3-substituted-phenylboronate produced by one of the methods of isolating a 4-chloro-2-fluoro-3-substituted-phenylboronate is also disclosed, wherein the 4-chloro-2-fluoro-3-substituted-phenylboronate may be obtained at a yield of greater than or equal to about 90%.

US Patent:

20130066115, Mar 14, 2013

Filed:

Sep 14, 2012

Appl. No.:

13/618128

Inventors:

Mark V. M. Emonds - Midland MI, US
Catherine A. Menning - Midland MI, US
D. Wayne Blaylock - Midland MI, US

Assignee:

DOW AGROSCIENCES LLC - Indianapolis IN

International Classification:

C07F 5/02
B01J 19/00

US Classification:

568 6, 422630, 422641

Abstract:

Methods for forming boronic acids, and intermediates thereof, are disclosed. The method may include mixing a 1-chloro-2-substituted-3-fluorobenzene starting material with an alkyllithium in a first reactor to form a reaction mixture. The 1-chloro-2-substituted-3-fluorobenzene starting material may react with the alkyllithium to form a lithiated intermediate. The reaction mixture may be continuously transferred to a second reactor and a borate may be continuously introduced to form a boronate. The boronic acids may be formed by treating the boronate with aqueous potassium hydroxide followed by acidification. Such methods may provide continuous formation of the boronic acids and may reduce an amount of a reactive intermediate present during processing as well as cycle times. Systems for forming the boronic acids are also disclosed.

US Patent:

20150239843, Aug 27, 2015

Filed:

May 13, 2015

Appl. No.:

14/711540

Inventors:

- Indianapolis IN, US
Catherine A. Menning - Midland MI, US
Daniel Randolph Henton - Midland MI, US

International Classification:

C07D 213/803

Abstract:

Methods of isolating a 4-chloro-2-fluoro-3-substituted-phenylboronate include adding carbon dioxide gas or carbon dioxide solid (dry ice) to a solution comprising a 4-chloro-2-fluoro-3-substituted-phenylboronate, an inert organic solvent, and at least one lithium salt to react the at least one lithium salt with the carbon dioxide gas or carbon dioxide solid (dry ice) and form a mixture comprising the 4-chloro-2-fluoro-3-substituted-phenylboronate, the inert organic solvent, and a precipitated solid. The precipitated solid may be removed from the mixture. Methods of using 4-chloro-2-fluoro-3-substituted-phenylboronates to produce methyl-4-amino-3-chloro-6-(4-chloro-2-fluoro-3-substituted-phenyl)pyridine-2-carboxylates are also disclosed. A 4-chloro-2-fluoro-3-substituted-phenylboronate produced by one of the methods of isolating a 4-chloro-2-fluoro-3-substituted-phenylboronate is also disclosed, wherein the 4-chloro-2-fluoro-3-substituted-phenylboronate may be obtained at a yield of greater than or equal to about 90%.