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A kind of preparation method of monofluoroolefin derivative

A technology of monofluoroolefins and derivatives, which is applied in the field of preparation of monofluoroolefin derivatives, can solve the problems of difficult preparation of fluorine-containing ylides, eliminate harsh reaction conditions, etc., achieve good application prospects, low equipment requirements, and high stereoselectivity Effect

Active Publication Date: 2022-02-15
LANZHOU INST OF CHEM PHYSICS CHINESE ACAD OF SCI +1
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

Common methods for synthesizing monofluoroolefin derivatives include: elimination reaction, fluorination reaction, oxidation elimination reaction, olefination reaction, metal-catalyzed reaction, etc. The elimination reaction conditions are relatively harsh, accompanied by aryl self-coupling products, olefination The reaction seems simple, but the preparation of fluorine-containing ylides is the difficulty

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  • A kind of preparation method of monofluoroolefin derivative
  • A kind of preparation method of monofluoroolefin derivative
  • A kind of preparation method of monofluoroolefin derivative

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preparation example Construction

[0019] One aspect of the embodiments of the present invention provides a method for preparing monofluoroolefin derivatives, which includes:

[0020] A mixed reaction system comprising fluorobenzenesulfonic acid compound, aldehyde compound, alkaline reagent and solvent is reacted to obtain a monofluoroalkene derivative; wherein, in the monofluoroalkene derivative, the cis monofluoroalkene derivative and the trans The ratio of monofluoroolefin derivatives is greater than 20:1.

[0021] In some more specific embodiments, the method specifically includes: adding the fluorobenzenesulfonic acid compound, the aldehyde compound and the solvent to the alkaline reagent and mixing to form the mixed reaction system, and then reacting 1- 4h, obtaining the monofluoroalkene derivative, wherein the ratio of the cis monofluoroalkene derivative to the trans monofluoroalkene derivative in the monofluoroalkene derivative is greater than 20:1.

[0022] Further, the reaction temperature is 60-80°C...

Embodiment 1

[0046] Weigh 1.8mmol 2-fluoro-1-phenyl-2-p-toluenesulfonyl-1-one, 1.5mmol benzaldehyde, and 1.8mmol DBU are added to the reaction tube, the volume of the reaction tube in this embodiment is 10mL, and A magnetic stirrer has been placed in advance, and then 1ml of acetonitrile is added to the reaction tube, and the above-mentioned reaction tube is placed on a magnetic stirrer, and stirred for 3 hours at 80°C; after the reaction is completed, the reaction solution is post-treated and recrystallized to obtain ( E) 0.35 g of pure product of -[2-fluoro(-2-benzenesulfonyl)vinyl]benzene, white solid, the yield is 90%.

[0047] The (E)-[2-fluoro(-2-benzenesulfonate) vinyl]benzene obtained above was tested for characterization:

[0048] figure 1 Shown is the H spectrum of (E)-[2-fluoro(-2-benzenesulfonate)vinyl]benzene, the purpose is to determine the structure and purity, 1 The characterization data of H-NMR is: 1 H-NMR (400MHz, Chloroform-d) δ8.06–7.99(m,2H),7.74–7.67(m,1H),7.63–7....

Embodiment 2

[0052] Weigh 1mmol 2-fluoro-1-phenyl-2-p-toluenesulfonyl-1-one, 0.1mmol 4-fluorobenzaldehyde, and 1.2mmol DBU into the reaction tube. The volume of the reaction tube in this example is 10mL. A magnetic stirrer has been placed in advance, and then 0.5ml of acetonitrile was added to the reaction tube, and the above reaction tube was placed on a magnetic stirrer, and stirred at 80°C for 3 hours; after the reaction, the reaction solution was post-treated and recrystallized Obtain 0.26 g of pure (E)-1-fluoro-4-[2-fluoro(-2-benzenesulfonyl)vinyl]benzene as a white solid with a yield of 91%.

[0053] A characterization test was performed on (E)-1-fluoro-4-[2-fluoro(-2-benzenesulfonyl)vinyl]benzene obtained above: 1 H-NMR (400MHz, Chloroform-d) δ8.02(d, J=7.4Hz, 2H), 7.70(d, J=7.4Hz, 1H), 7.62(d, J=8.5Hz, 2H), 7.58( q, J=3.9Hz, 2H), 7.10(d, J=8.3Hz, 2H), 7.03(d, J=28.7Hz, 1H). 13 C-NMR (101MHz, Chloroform-d) δ163.6(dd, J=252.6, 3.6Hz), 153.3(d, J=303.9Hz), 137.4, 134.6, 132.4(t, J=8...

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Abstract

The invention discloses a preparation method of a monofluoroolefin derivative. The preparation method of the monofluoroolefin derivative includes: reacting a mixed reaction system comprising a fluorobenzene sulfonic acid compound, an aldehyde compound, a basic reagent and a solvent to obtain a monofluoroolefin derivative; wherein, the monofluoroolefin derivative The ratio of cis-monofluoroalkene derivatives to trans-monofluoroalkene derivatives is greater than 20:1. The monofluoroolefin derivative prepared by the present invention has high stereoselectivity and a yield of as high as 80%-97%. At the same time, the preparation method of the present invention has a wide range of raw material sources, mild reaction conditions, environmental friendliness, low equipment requirements, and is suitable for Industrial production.

Description

technical field [0001] The invention belongs to the technical field of organic chemical synthesis, and in particular relates to a preparation method of monofluoroolefin derivatives. Background technique [0002] Fluorine-containing compounds are a very important class of organic compounds, which exist in every aspect of our lives. Since the appearance of the first fluorine-containing drug in 1957, fluorine-containing drugs have been developed rapidly for more than half a century. So far, 20%-25% of medicines and 30%-40% of pesticides contain at least one fluorine atom. People have a very large demand for fluorine-containing compounds, but the amount of naturally occurring fluorine-containing compounds is very small. Therefore, a large number of fluorine-containing compounds are prepared by chemical synthesis. [0003] As an important class of fluorine-containing compounds, monofluoroalkene derivatives have received extensive attention in the research of materials science a...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07C315/04C07C317/14C07C317/22C07C17/361C07C22/08
CPCC07C315/04C07C17/361C07C317/14C07C317/22C07C22/08
Inventor 蒋高喜康磊钱金龙杨化萌
Owner LANZHOU INST OF CHEM PHYSICS CHINESE ACAD OF SCI