Methods of Fluorinating Compounds

A fluorination, cyanide technology, applied in organic chemistry methods, chemical instruments and methods, organic chemistry, etc., can solve problems such as poor selectivity and reactivity

Inactive Publication Date: 2019-07-05
DOW AGROSCIENCES LLC +1
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

[0007] Although TBAF* has been successfully used in some systems, it still has limitations, such as poor selectivity and reactivity for difficult-to-fluorinate substrates such as chloropyridines, especially the 6-arylpicolinate family
Other limitations include that TBAF* must be pre-formed for each batch of reactions, and fluorination has only been demonstrated in DMSO

Method used

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  • Methods of Fluorinating Compounds
  • Methods of Fluorinating Compounds
  • Methods of Fluorinating Compounds

Examples

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Embodiment

[0097] The following examples are set forth to illustrate methods, compositions, and results in accordance with the disclosed subject matter. These examples are not intended to cover all aspects of the subject matter disclosed herein, but rather illustrate representative methods, compositions, and results. These examples do not exclude equivalents and modifications of the present invention, which are obvious to those skilled in the art.

[0098] Efforts have been made to ensure accuracy with respect to numbers (eg, amounts, temperature, etc.), but some errors and deviations should be accounted for. Unless indicated otherwise, parts are parts by weight, temperature is in degrees Celsius (° C.) or is at ambient temperature, and pressure is at or near atmospheric. There are many variations and combinations of reaction conditions, eg, component concentrations, temperatures, pressures, and other reaction ranges and conditions that can be used to optimize product purity and yield o...

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Abstract

A method of preparing a fluorinated aryl or heteroaryl substrate by mixing a quaternary ammonium cyanide and an aryl or heteroaryl substrate substituted with at least one chlorine, bromine, sulfonyl, or nitro group to obtain a mixture, and The mixture is mixed with hexafluorobenzene to obtain the fluorinated substrate.

Description

[0001] Cross References to Related Applications [0002] This application claims the benefit of US Provisional Patent Application 61 / 902,979, filed November 12, 2013, and US Provisional Patent Application 61 / 985,224, filed April 28, 2014, the entire disclosures of which are expressly incorporated herein by reference. technical field [0003] This application relates generally to methods of fluorinating aryl or heteroaryl compounds and the fluorinated compounds. Background technique [0004] Fluorinated organic molecules are increasingly used in the life sciences industry. The presence of fluorine substituents may have a positive effect on the biological properties of the compounds. Synthetic techniques for fluorinating compounds are therefore an important area of ​​interest. [0005] Selective fluorination of aryl and heteroaryl substrates is a challenging synthetic problem. For example, monochloro- and dichloro-substituted picolinates are difficult to fluorinate and requ...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07D213/803
CPCC07C17/20C07C25/24C07D213/02C07D213/79C07D213/803C07B39/00
Inventor L·艾伦M·桑福德D·布兰德
Owner DOW AGROSCIENCES LLC
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