Aryl high-iodine trifluoromethylated reagent and preparation and application thereof

A technology of aryl trifluoromethyl and phenyl trifluoromethyl iodine chloride is applied in the preparation of carbon-based compounds, the preparation of organic compounds, the preparation of hydrogenated polysulfides/polysulfides, etc. Aryl trifluoromethyl periodide lacks direct and effective methods and other problems, and achieves the effects of diverse structures, efficient preparation, and direct preparation methods

Active Publication Date: 2018-03-06
NORTHEAST NORMAL UNIVERSITY
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0004] At present, there are few types of electrophilic trifluoromethylation reagents, and there is still a lack of direct and effective methods for the preparation of simple, structurally adjustable aryl trifluoromethyl periodides.

Method used

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  • Aryl high-iodine trifluoromethylated reagent and preparation and application thereof
  • Aryl high-iodine trifluoromethylated reagent and preparation and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0048] Preparation of phenyltrifluoromethyl iodine chloride:

[0049] In a 15 mL round bottom flask, add 0.5 mmol bis(trifluoroacetic acid) iodobenzene, under anhydrous nitrogen protection environment, add 0.75 mmol potassium fluoride and 1.0 mL MeCN, add 0.75 mmol trifluoromethyl Trimethylsilane. After stirring for 21 hours, the reaction mixture was poured into a mixed solution of 20 mL of 15% aqueous sodium chloride and 10 mL of acetone at 0 °C. The mixed solution was extracted with dichloromethane (20 mL, 3 times), and the organic phases in the extracted mixed solution were combined and dried over anhydrous magnesium sulfate. After distilling off the solvent, the crude product was washed with petroleum ether to obtain a white solid, phenyltrifluoromethyl iodine chloride, with a yield of 86%.

[0050] NMR and MS characterization of phenyltrifluoromethyl iodine chloride: 1 H NMR (600 MHz, DMSO-d 6 ) δ 8.31(d, J = 8.4 Hz, 2H), 7.72 (t, J = 7.5 Hz, 1H), 7.57 (t, J = 7...

Embodiment 2

[0052] Preparation of 4-fluorophenyltrifluoromethyl iodine chloride

[0053] In a 15 mL round bottom flask, add 0.5 mmol 4-fluoro-bis(trifluoroacetic acid) iodobenzene, under anhydrous nitrogen protection environment, add 0.75 mmol potassium fluoride and 1.0 mL acetonitrile, add 0.75 mmol Trifluoromethyltrimethylsilane. After stirring for 21 hours, the reaction mixture was poured into a mixed solution of 20 mL of 15% aqueous sodium chloride and 10 mL of acetone at 0 °C. Extract with dichloromethane (20 mL, 3 times). The organic phases in the extracted mixed solution were combined and dried with anhydrous magnesium sulfate. Dry over anhydrous magnesium sulfate. After distilling off the solvent, the crude product was washed with petroleum ether to obtain a white solid, 4-fluorophenyltrifluoromethyl iodine chloride, with a yield of 65%.

[0054] NMR and MS characterization of fluorophenyl trifluoromethyl iodine chloride: 1 H NMR (600 MHz, CDCl 3 , δ): 8.14~8.11 (m, 2H), 7.7...

Embodiment 3

[0056] Preparation of Phenyltrifluoromethyl Iodine Fluoride

[0057] In a 15 mL round bottom flask, add 0.5 mmol bis(trifluoroacetic acid) iodobenzene, under anhydrous nitrogen protection environment, add 0.75 mmol potassium fluoride and 1.0 mL MeCN, add 0.75 mmol trifluoromethyl Trimethylsilane. After stirring for 24 hours, the reaction mixture was poured into a mixed solution of 20 mL of 15% potassium fluoride aqueous solution and 10 mL of acetone at 0 °C. Extract with dichloromethane (20 mL, 3 times). The organic phases in the extracted mixed solution were combined and dried with anhydrous magnesium sulfate. Dry over anhydrous magnesium sulfate. After distilling off the solvent, the crude product was washed with petroleum ether to obtain a white solid, phenyltrifluoromethyl iodine fluoride, with a yield of 56%.

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Abstract

The invention discloses an aryl high-iodine trifluoromethylated reagent and also provides a preparation method of the reagent. An aryl trifluoromethyl high-iodine substance is prepared by carrying outa direct cationic ligand exchange reaction on high-iodine substances including ArIY2 and TMSCF3, and then is developed into the efficient trifluoromethylated reagent. The high-iodine trifluoromethylated reagent can be prepared directly, concisely and efficiently. The reagent is table and high in reaction activity, can be used for various high-iodine trifluoromethylated reactions, and is free of catalysts (a Togni trifluoromethylated reagent needs to be activated by a catalyst when used). The reagent disclosed by the invention overcomes the defects that in the prior art, high-iodine trifluoromethylated reagents have few types, single structure and tedious synthetic steps, and the noncyclic aryl trifluoromethyl high-iodine trifluoromethylated reagent provided by the invention has various structures and direct and simple preparation method.

Description

technical field [0001] The invention discloses an arylperiodine trifluoromethylation reagent, and also provides a preparation method of the reagent, further discloses the use of the reagent in the field of organic synthesis methodology, and belongs to the technical field of organic synthesis chemistry. Background technique [0002] Compounds containing trifluoromethyl often have significantly enhanced physical and chemical properties and biological activities, and are widely used in medicine, pesticides, dyes, energy, materials and other fields. Especially in the field of medicine, fluorine-containing drugs account for nearly 30%. For example, among the fluorine-containing drugs approved in the past three years, 17 are fluorinated aromatic hydrocarbons, and 6 contain trifluoromethyl. [0003] Aryl perfluoroalkyl periodide (ArI(C n f 2n-1 )X) is a highly efficient electrophilic perfluoroalkyl transfer reagent. Among them, the simplest perfluoroalkyl group is trifluoromethy...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C25/13C07C17/35C07C69/63C07C67/30C07C49/80C07C45/00C07C321/14C07C319/22C07B39/00
CPCC07B39/00C07C17/35C07C25/13C07C45/008C07C67/30C07C69/63C07C319/22C07C49/80C07C321/14
Inventor 王芒许聪郭佳刘群
Owner NORTHEAST NORMAL UNIVERSITY
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