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A compound containing monofluorochloromethylthiosulfonate, its preparation method and application

A compound, the technology of sodium phenylsulfinate, applied in the preparation of sulfide, organic chemistry, etc., can solve the problems of low yield, less research, and high difficulty, and achieve high yield, high application yield, and high purity Effect

Active Publication Date: 2021-09-03
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

[0006] The purpose of the present invention is to overcome the shortcomings of the current method of directly introducing a fluorochloromethylthio group in the art, such as less research, difficulty, and low yield, and then to provide a method containing a fluorochloromethylthiosulfonic acid Ester compound, preparation method and application

Method used

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  • A compound containing monofluorochloromethylthiosulfonate, its preparation method and application
  • A compound containing monofluorochloromethylthiosulfonate, its preparation method and application
  • A compound containing monofluorochloromethylthiosulfonate, its preparation method and application

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Experimental program
Comparison scheme
Effect test

Embodiment 1

[0121] The preparation of embodiment 1-fluorochloromethylthiobenzenesulfonate

[0122] The preparation of a fluorochloromethylthiobenzenesulfonate is divided into two steps:

[0123] step 1):

[0124]

[0125] Take a 500mL three-necked bottle, add 200mL of n-hexane, and pass through CFCl 2H gas, about 1.5h ventilation. Then take 1 mL of n-hexane solution and add benzotrifluoride as an internal standard. The concentration of the solution is about 3 mmol / mL, and it contains a total of 600 mmol of fluorodichloromethane. Then NaOH (400mmol, 16.0g, 4.0equiv), PhCH 2 SH (100mmol, 12.4g, 1.0equiv), phase transfer catalyst Tris(2-(2-methoxyethoxy)ethyl)amine (8mmol, 2.5g, 0.08equiv), transferred to an oil bath, refluxed at 60°C for 4h. After the reaction, cool to room temperature, spin dry n-hexane, transfer to a 50mL egg-shaped bottle, and distill under reduced pressure with an oil pump (oil bath temperature 70°C, collect fractions at 38-43°C) to obtain 4.0g of a colorless oil...

Embodiment 2

[0131] Example 2 The condition exploration example of reagent and aryl boronic acid coupling reaction

[0132] The general procedure for this coupling reaction is: under the protection of argon, 0.9mmol aryl boronic acid, 0.5mmol reagent, 0.05mmol copper sulfate, 0.75mmol sodium bicarbonate, 5mL methanol in a 25mL sealed tube, react at room temperature for 12h. After the reaction was completed, 10 mL of water was added, extracted with anhydrous ether, dried over anhydrous magnesium sulfate, filtered with diatomaceous earth, concentrated, and the desired product was obtained by column chromatography.

[0133] Examples of conditional exploration are described in Table 1:

[0134] Table 1

[0135]

[0136] In table 1, [M] refers to catalyzer, and R refers to the mol ratio of alkali and reagent, and Base refers to alkali, 19 F yield (%) refers to the yield calculated by tracking the fluorine spectrum.

Embodiment 3

[0138]

[0139] Operation steps: under the protection of argon, weigh 0.9mmol boric acid, 0.5mmol reagent, 0.05mmol copper sulfate, 0.75mmol sodium bicarbonate, 5mL methanol in a 25mL sealed tube, and react at room temperature for 12h. After the reaction, 10 mL of water was added, extracted with anhydrous ether, dried over anhydrous magnesium sulfate, filtered through celite, concentrated, and the residue was subjected to flash silica gel column chromatography to obtain 108 mg of a white solid with a yield of 85%.

[0140] 1 H NMR (400MHz, CDCl 3 )δ7.73-7.57 (m, 5H), 7.50 (t, J = 7.5Hz, 2H), 7.42 (m, 1H), 7.12 (d, J = 56.0Hz, 1H); 19 F NMR (376MHz, CDCl 3 )δ-98.96(d, J=55.9Hz); 13 C NMR (101MHz, CDCl 3 )δ143.03, 139.92, 135.40, 135.39, 129.05, 128.10, 127.84, 127.26, 104.56 (d, J = 282.9Hz) ppm.IR (KBr): v = 1477, 1397, 1227, 1209, 1116, 1000, 837cm -1 .MS(EI):185(100),197,217,252.HRMS(EI):calculated value C 13 h 10 FClS: 252.0176, measured value: 252.0183.

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Abstract

The invention discloses a compound containing monofluorochloromethylthiosulfonate represented by formula 1, a preparation method and application thereof. The preparation method of the compound shown in formula 1 includes the following steps: reacting with sodium phenylsulfinate in chlorine gas solution. The compound shown in formula 1 of the present invention can be used as a fluorochloromethylthiolation reagent, and its application yield is high, thereby providing an important methodological research tool for the fields of medicine, pesticides and materials.

Description

technical field [0001] The invention relates to a compound containing monofluorochloromethylthiosulfonate, its preparation method and application. Background technique [0002] Fluorine atom has higher electronegativity (Pauling electronegativity: 3.98), smaller atomic radius As well as particularly low polarizability, these properties give fluorides special physicochemical properties (Chem. Rev. 2005, 105, 827). The introduction of fluorine atoms into organic molecules can change the physical, chemical and biological properties of molecules, and guide the absorption, distribution, metabolism and excretion characteristics of almost all lead compounds in organisms. As a result, fluorinated organics are increasingly used in medicine, pesticides, materials, and positron emission tomography tracers. Recently, more and more popular PET (position emission tomography) imaging 18 F mark, using the 18 F only uses the characteristics of a half-life of 110min and a linear range ...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07C323/03C07C323/07C07C323/20C07C323/22C07C323/62C07C381/04C07D307/79C07D307/91C07D317/62C07D327/06C07D333/76C07D339/08C07C319/14
CPCC07C323/03C07C323/07C07C323/20C07C323/22C07C323/62C07C381/04C07D307/79C07D307/91C07D317/62C07D327/06C07D333/76C07D339/08
Inventor 沈其龙吕龙赵群超
Owner SHANGHAI INST OF ORGANIC CHEM CHINESE ACAD OF SCI
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