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Application of Trivalent Iodine Compounds as Catalysts in Balz-schiemann Reaction

A compound, technology of trivalent iodine, applied in the field of application of trivalent iodine compounds as catalysts in Balz-Schiemann reaction, can solve problems such as high risk, high reaction temperature, and difficult operation

Active Publication Date: 2021-03-23
SHANGHAI INST OF ORGANIC CHEM CHINESE ACAD OF SCI
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0011] The technical problem to be solved by the present invention is to overcome the technical problems such as severe reaction conditions (such as high reaction temperature), narrow substrate application range, high risk, difficult operation, etc. when Balz-Schiemann reaction uses chemical methods in the prior art, and Provided is the application of a trivalent iodine compound as a catalyst in the Balz-Schiemann reaction

Method used

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  • Application of Trivalent Iodine Compounds as Catalysts in Balz-schiemann Reaction
  • Application of Trivalent Iodine Compounds as Catalysts in Balz-schiemann Reaction
  • Application of Trivalent Iodine Compounds as Catalysts in Balz-schiemann Reaction

Examples

Experimental program
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Effect test

Embodiment 35

[0166] Under the protection of nitrogen, add (92.5mg, 0.5mmol), the BF 3 ·OEt 2 (1.25mmol) was dissolved in 2.5mL trifluorotoluene and added to the above sealed tube, then the reaction temperature was lowered to 0°C, tBuONO (0.9mmol) was added dropwise, maintained at 0°C for 15 minutes, and 2.5mL (28.0mg, 0.1mmol) in trifluorotoluene, sealed and heated at 40°C for 36 hours. Cool to room temperature, column chromatography, petroleum ether and ethyl acetate as developing solvent, to obtain the product 60.2mg, 64%.

Embodiment 36

[0168] Add 10mmol of aniline to a 50mL eggplant-shaped bottle, add 3.0mL of EtOH to dissolve, add 50% HBF dropwise 4 Aqueous solution 2.5mL (2.4 equivalents), stirred for 5min, cooled to 0°C in ice-water bath, added dropwise t BuONO 2.7mL (2.6eq), returned to room temperature and stirred for 1 hour. Add 30 mL of anhydrous diethyl ether, stir for 10 min, collect the product by filtration, wash with anhydrous diethyl ether three times, and drain it with an oil pump. The obtained product is directly used for the reaction.

Embodiment 37

[0170] Add 5mmol of aniline to a 25mL eggplant-shaped bottle, add H 2 O 1.0mL was dissolved, and 50% HBF was added dropwise 4 Aqueous solution 1.9mL (3.1 equivalents), stirred for 5min, cooled to 0°C in ice-water bath, added dropwise NaNO 2 Aqueous solution 1.0mL (NaNO 2 680 mg, 2.0 equivalents). Keep stirring in an ice-water bath for 30 min, collect the product by filtration, wash twice with ice water, twice with anhydrous EtOH, twice with anhydrous ether, and drain with an oil pump. The obtained product is directly used for the reaction.

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Abstract

The invention discloses an application of trivalent iodine compounds shown in formula I and / or II in the description and used as catalysts in Bal-Schiemann reaction. The trivalent iodine compounds areused as the catalysts in the Bal-Schiemann reaction, so that the Bal-Schiemann reaction can be conducted at room temperature or near room temperature when a thermochemical method is used, and the reaction has mild reaction conditions, wide substrate use range and short reaction time, and is safe and easy to operate, products are easy to separate, and raw materials are simple and low in toxicity.

Description

technical field [0001] The invention relates to the application of a trivalent iodine compound as a catalyst in the Balz-Schiemann reaction. Background technique [0002] Because fluorine atoms have the largest electronegativity and smaller atomic radius, the introduction of fluorine atoms or fluorine-containing dices in molecules can often change the physical and chemical properties of organic molecules. Therefore, fluorine-containing compounds are getting more and more attention in the fields of medicine, pesticides and materials ((a) Kirsch, P.Modern Fluoroorganic Chemistry: Synthesis, Reactivity, Applications; Wiley-VCH: Weinheim, 2004. (b) Organofluorine Compounds : chemistry and Applications; Hiyama, T., Ed.; Springer: New York, 2000.). Direct fluorination method: that is to directly introduce fluorine atoms into molecules, is a better way to achieve the above purpose and is widely used. [0003] For aromatic compounds, the fluorination method can be divided into cou...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07C17/093C07C25/13C07C25/22C07C25/18C07C41/22C07C43/225C07C43/29C07C45/63C07C49/807C07C67/307C07C69/65C07C51/363C07C63/70C07C253/30C07C255/50C07C303/40C07C311/08C07C69/76C07D213/79C07D215/18C07D311/30C07D311/58C07J1/00B01J31/02
CPCB01J31/0231B01J31/0232B01J2231/4277C07C17/093C07C25/13C07C25/18C07C25/22C07C41/22C07C43/225C07C43/29C07C45/63C07C49/807C07C51/363C07C63/70C07C67/307C07C69/65C07C69/76C07C253/30C07C255/50C07C303/40C07C311/08C07D213/79C07D215/18C07D311/30C07D311/58C07J1/0059C07C2603/18
Inventor 胡金波邢博
Owner SHANGHAI INST OF ORGANIC CHEM CHINESE ACAD OF SCI