45 results about "Trifluoromethylation" patented technology

The invention discloses a preparation method for direct trifluoromethylation of pyrimidinedione herbicides under visible light catalysis, and belongs to the technical field of photocatalytic organic synthesis and the technical field of pesticide herbicides. The preparation method for direct trifluoromethylation of the pyrimidinedione weeding drug under visible light catalysis comprises the following steps: S1, mixing a photocatalyst, the pyrimidinedione weeding drug, a trifluoromethylation reagent, copper acetate, triethylamine and dimethyl sulfoxide, and carrying out a photocatalytic reaction under visible light; s2, after the reaction is finished, adding a saturated sodium chloride solution and dichloromethane for extraction, and collecting an organic phase; and S3, concentrating the organic phase, and purifying through silica gel column chromatography to obtain the 5-trifluoromethylated pyrimidinedione product. The method provided by the invention uses visible light energy as an energy source, has the advantages of simple operation, low cost and the like, and fills the vacancy of direct trifluoromethylation of pyrimidinedione herbicides.

The invention belongs to the technical field of organic synthetic chemistry, and discloses green and mild trifluoromethylated pyridino [1, 2-a] indole, a synthetic method and application, the method comprises the following steps: taking trifluoromethylsulfonyl pyridinium salt as a fluoroalkylation reagent under photocatalysis, and reacting the reagent with N-substituted indole to obtain the trifluoromethylated pyridino [1, 2-a] indole. According to the method, high-temperature reaction is not needed, the condition is mild, and the tolerance to a reaction substrate is good. According to the method disclosed by the invention, a photosensitizer and a metal catalyst are not needed in the reaction process, the synthetic route is green and environment-friendly, and the trifluoromethylated pyrido [1, 2-a] indole derivative can be rapidly and efficiently synthesized.

A combination of a trifluoromethyl-containing compound and a furopyrrole-containing compound for use in treating blood tumors. Specifically, the invention relates to the use of a combination of formula (I-1) or a pharmaceutically acceptable salt thereof and a compound of formula (II-1) or a pharmaceutically acceptable salt thereof in the treatment of blood tumors.

The invention belongs to the technical field of organic synthesis, and discloses a preparation method for trifluoromethylation of a 1, 6-enyne substrate. The preparation method comprises the following steps: in a protective gas atmosphere, mixing a 1, 6-eneyne substrate, NaSO2CF3, an oxidant, N-bromosuccinimide and an organic solvent, heating to react, cooling, separating an organic phase, drying and purifying to obtain a product after trifluoromethylation of the 1, 6-eneyne substrate, the organic solvent is selected from any one of dimethoxyethane and 1, 2-dichloroethane. The preparation method is mild in reaction condition, simple and convenient to operate, good in substrate applicability, good in substrate selectivity in reaction and high in target product yield, and a new way is provided for trifluoromethylation of the 1, 6-eneyne compound.

The application relates to the field of organic synthesis, in particular to a method for synthesizing beta-trifluoromethylsulfinyl ketone derivatives by ring-opening of cyclopropanol. 3 C intermediates, and then adding a trifluoromethylating agent S-trifluoromethyl-4-methylthiobenzenesulfonate to obtain beta-trifluoromethylsulfinyl ketone derivatives. The application uses the simple, easy-to-prepare and stable S-trifluoromethyl-4-methylthiobenzenesulfonate as a trifluoromethylating agent, and the reaction condition is mild, and the synthesis method is simple and easy to operate.

The invention discloses a preparation method of fluoroolefin, and belongs to the technical field of organic chemistry. The preparation method of the fluoroolefin is based on a silicon free radical mediated trifluoromethylation strategy, a SiEt3-Bpin silane reagent is used as a silicon free radical source, a transition metal catalyst is not needed, and potential harm of metal to the environment is effectively avoided. Meanwhile, by directly using the fluoroalkyl ketone which is low in price and easy to obtain as the starting substrate, the complex functionalization step in the traditional trifluoromethylation process is simplified. In addition, the silicon free radical mediated trifluoromethyl hydrazone realizes efficient synthesis of fluorine-containing olefin with single configuration in the double bond migration process, and a novel green, efficient and universal method is provided for construction of fluoroolefin with high trans-selectivity.

The present invention discloses a class of chiral bis(trifluoromethylated) spirobenzothiophenone-fused pyrrolidine derivatives, belonging to the technical field of organic chemical synthesis. The preparation method is to dissolve the trifluoroethylimine (I) derived from benzothiophenedione and β-trifluoromethyl ketene (II) in an organic solvent, then add a chiral catalyst, and stir and react at room temperature. After the reaction is completed, the product (III) is obtained by separation and purification; the bis(trifluoromethylated) spirobenzothiophenone-fused pyrrolidine derivatives provided by the present invention have four consecutive chiral centers and easily functionalizable groups, which are convenient for the derivation and synthesis of other chiral polycyclic compounds, can provide more candidate molecules for the research and development of new drugs and the screening of drugs, and these compounds show good application prospects in anti-tumor aspects; the preparation method of the present invention has the advantages of novelty, simplicity, easy operation, mild reaction conditions, high yield, and high stereoselectivity.

The application provides a preparation method of an electrocatalytic SCF-substituted dihydrofuran compound, and belongs to the technical field of compound preparation. The application uses diazonium and ethylene compounds as substrates, uses an SCF source as a sulfur-containing and fluorine-containing fragment donor, realizes a one-pot cascade reaction of ring formation through electrolysis, and thus constructs the SCF-substituted dihydrofuran compound. The raw material of the application has a wide source, uses electric current as a reaction driving force, avoids or reduces the use of additional photosensitizers and chemical oxidation-reduction reagents, and has the one-pot cascade characteristics of ring C-N bond breaking, C-O bond construction, trifluoromethylation and ring formation and the like, so that the step economy can be improved.

The application provides a method for photocatalytic functionalization of C(sp 3 )‑Cl bond at the benzyl position and application thereof. The method comprises the following steps: adding a photocatalyst, a benzyl chloride compound and a functionalization reagent into a solvent, and then adding or not adding a base to obtain solution A; irradiating solution A with light under an inert atmosphere to obtain a functionalization product at the benzyl position; wherein the photocatalyst is selected from copper-n-heterocyclic carbene complexes; the functionalization comprises trifluoromethylation, cyanation or amination. The method can be carried out under normal temperature and pressure in an inert atmosphere, and uses a cheap transition metal copper-n-heterocyclic carbene complex as a catalyst, and cooperates with a functionalization reagent to capture the chlorine atom of the C(sp 3 )‑Cl bond at the benzyl position of the benzyl chloride compound under light irradiation to obtain a benzyl radical, the benzyl radical is captured by the copper-n-heterocyclic carbene complex, and the benzyl radical is reduced and eliminated to obtain the functionalization product at the benzyl position. The reaction has the advantages of mild conditions, no need of additional precursors or reducing agents, wide application range of substrates and high reaction efficiency.

The invention discloses a high Z / E selectivity heteroatom-trifluoromethylation reaction for photocatalysis of alkyne, which is a novel alkyne heteroatom-trifluoromethylation reaction mediated by visible light photooxidation reduction catalysis, and comprises the following steps: taking an alkyne compound, a free radical scavenger and CF3SO2Na as raw materials, using a photocatalyst, and carrying out a reaction for 20-30min to obtain the high Z / E selectivity heteroatom-trifluoromethylation reaction of the light-catalyzed alkyne, the high Z / E selectivity heteroatom-trifluoromethylation reaction of the light-catalyzed alkyne, and the high Z / E selectivity heteroatom-trifluoromethylation reaction of the light-catalyzed alkyne. The method comprises the following steps of: performing irradiation reaction under blue light at room temperature to obtain heteroatom-alkene-CF3, and adjusting reaction conditions to obtain a specific Z / E product with high selectivity.

The present invention develops a method for blue light induced hydrogen trifluoromethylation of alkynyl compounds. The method uses alkynyl compounds and sodium trifluoromethanesulfinate as raw materials, and uses sodium trifluoromethanesulfinate as a trifluoromethyl source to carry out hydrogen trifluoromethylation of alkynyl groups under blue light irradiation at room temperature to obtain C-containing vinyl This method has the advantages of a wide substrate range, mild reaction conditions, high yield of target product, simple reaction operation, low reaction pollution, and is feasible for industrial large-scale production.

The application discloses a preparation method of 2,2'-di(trifluoromethyl)-4,4',5,5'-biphenyl dianhydride, which comprises the following steps: ① iodization reaction of o-xylene to obtain 1,2-diiodo-4,5-xylene; ② coupling reaction of the product of step ① to obtain 2,2'-diiodo-4,4',5,5'-tetramethyl biphenyl; ③ trifluoromethylation of the product of step ② to obtain 2,2'-di(trifluoromethyl)-4,4',5,5'-tetramethyl biphenyl; ④ oxidation of the product of step ③ with an oxidant to obtain 2,2'-di(trifluoromethyl)-4,4',5,5'-biphenyl tetraacid; and ⑤ dehydration and cyclization of the product of step ④ to obtain 2,2'-di(trifluoromethyl)-4,4',5,5'-biphenyl dianhydride. The synthetic route provided by the application has the advantages of mild reaction condition, simple treatment, high efficiency and low cost.

The invention discloses a green synthesis process of 2-amino-3-chloro-5-trifluoromethylpyridine, and belongs to the technical field of preparation of pesticide intermediates. The method comprises the following steps: by taking 3, 5-dichloropyridine as a raw material, carrying out nitrogen-oxidation reaction; then carrying out trifluoromethylation reaction under the action of a palladium catalyst; then carrying out chlorination reaction on phosphorus oxychloride; and finally, carrying out ammonification reaction to generate the 2-amino-3-chloro-5-trifluoromethylpyridine. According to the method, all the raw materials can be conveniently purchased on the market, the process of each step of reaction is simple and convenient, chloropyridine is directly subjected to trifluoromethylation by adopting trifluoromethyl potassium trifluoroborate and a palladium catalyst, the reaction yield is high, and industrial production is easy; meanwhile, a by-product ammonia chloride generated in the mother liquor in the amino substitution step can be recycled as a by-product.

The application belongs to the field of antitumor drugs, and particularly relates to trifluoromethylated temozolomide and derivatives thereof, a preparation method and application. The trifluoromethylated temozolomide has a better killing effect on tumor cells relative to traditional temozolomide, has a lower toxic effect on normal neuron cells at a low concentration relative to temozolomide, and can penetrate the blood-brain barrier through animal experiments.

The application relates to a synthesis method of 2-(trifluoromethyl)thiazole compounds, characterized in that the synthesis method uses a thiazole compound without substitution at the 2 position as a raw material, cuprous chloride as a catalyst, p-benzoquinone as an oxidant, (trifluoromethyl)trimethylsilane as a trifluoromethylating reagent in the presence of a base, and high-selectivity 2-(trifluoromethyl)thiazole compounds are generated. The synthesis method not only uses cheap and easily-obtained catalysts and oxidants, and does not need ligands, but also realizes the C-H bond activation trifluoromethylation which is difficult to realize in the prior art. The synthesis method is high in atom economy, simple and easy to operate, high in regioselectivity, and suitable for industrial scale production.

This invention discloses a method for synthesizing trifluoromethylated polycyclic indole derivatives using visible light photocatalysis, belonging to the field of organic synthesis technology. This invention is the first to disclose a method for synthesizing trifluoromethylated polycyclic indole derivatives under visible light photocatalysis via CF3Br and... N This invention relates to a method for the one-step preparation of trifluoromethylated polycyclic indole derivatives, namely 2,3-dihydropyrrolo[1,2-a]indole and 5,6-dihydroindole[2,1-a]isoquinoline derivatives, through a free radical cyclization reaction of alkenyl indole derivatives. This invention is the first to use CF3Br as a trifluoromethylating agent, via CF3Br reacting with... N The radical cyclization reaction of α-alkenyl indole derivatives successfully constructed trifluoromethylated 2,3-dihydropyrrole[1,2-a]indole and 5,6-dihydroindole[2,1-a]isoquinoline derivatives. Compared with other trifluoromethylating reagents used in the prior art, CF3Br has the advantages of low cost, easy availability and high atom utilization. Compared with the existing synthetic methods, the method provided by this invention greatly reduces the synthesis cost and has a high possibility of large-scale production.

The invention discloses a preparation method of 4-chloro-3-trifluoromethylaniline, and belongs to the technical field of medical intermediates. The preparation method comprises the following steps: brominating 4-chlorophenylboronic acid serving as a raw material, protecting boric acid by adopting MIDA, and then carrying out trifluoromethylation reaction in the presence of a palladium catalyst, or directly carrying out trifluoromethylation reaction on a brominated product; and finally, carrying out ammonolysis reaction to generate the 4-chloro-3-trifluoromethylaniline. According to the method, all the raw materials can be conveniently purchased on the market, the bromination reaction and the trifluoromethylation reaction are high in selectivity and good in yield, and the route operability is high.

The invention discloses a preparation method of 2-(2-methyl-3-(trifluoromethyl) anilino) nicotinic acid (flunixin). 2-methyl-3-chloroaniline is used as a raw material, a 2-methyl-3-trifluoromethylaniline intermediate is obtained through diazo iodination, trifluoromethylation and ammonolysis, and finally the 2-methyl-3-trifluoromethylaniline intermediate is coupled with 2-chloronicotinic acid to synthesize flunixin. The flunixin obtained in the process is an off-white solid, the purity is 98%, and the total yield of the whole process is 49.6%. The preparation method of flunixin is specifically limited, and on the premise of obtaining high yield, the whole steps are simple to operate, and the flunixin is easy to prepare.

The invention discloses a synthesis method of (R)-1-(2-bromine-4-chlorphenyl)-2, 2, 2-trifluoroethanol, and relates to the technical field of organic synthesis.The synthesis method comprises the steps that 2-bromine-4-chlorobenzoic acid methyl ester serves as a raw material, trifluoromethylation is conducted on the 2-bromine-4-chlorobenzoic acid methyl ester, and a 2-bromine-4-chlorphenyl trifluoroethanone acetal intermediate solution is obtained; the preparation method comprises the following steps: preparing a 2-bromo-4-chlorophenyl trifluoroethanone acetal intermediate solution, carrying out ketal deprotection on the 2-bromo-4-chlorophenyl trifluoroethanone acetal intermediate solution to obtain 2-bromo-4-chlorophenyl trifluoroethanone, and carrying out chiral reduction synthesis on the 2-bromo-4-chlorophenyl trifluoroethanone to obtain (R)-1-(2-bromo-4-chlorophenyl)-2, 2, 2-trifluoroethanol. The method is low in cost, easy to operate and implement, high in yield and stable in product property.

A process for synthesizing N-CF3 compounds, including N-CF3 sulfonamides and analogues thereof is disclosed. Starting materials for these syntheses include compounds with acidic N-H groups which are converted into dithiocarbamates, and then these dithiocarbamates are fluorinated to obtain N-CF3 compounds using a combination of oxidants and fluorination reagents. The reagents used in these steps are readily available and have relatively low hazard levels. The reactions can be carried out under mild conditions, for example, at or below room temperature, and can be scaled-up since the reagents can be readily obtained in large quantities. High-purity yields can be obtained. In addition, the compounds N-methyl-N-(trifluoromethyl)methanesulfonamide, having the formula H3CSO2N(CF3)(CH3), and 2-(trifluoromethyl)isothiazolidine 1,1 -dioxide, having the formula H6CSO2N(CF3), are disclosed.

The invention discloses a low-dielectric spherical ceramic powder and polyphenyl ether composite dielectric material for a 5G substrate, and belongs to the technical field of organic polymer materials. The composite material is prepared from the following components in parts by weight: 25 to 60 parts of modified polyphenyl ether, 30 to 60 parts of spherical ceramic powder modified by a sulfydryl silane coupling agent, 0.01 to 5 parts of a compatibilizer, 0.5 to 3 parts of an antioxidant, 0.5 to 2 parts of a release agent and 0.1 to 0.6 part of an initiator, the modified polyphenyl ether is prepared from side chain brominated methyl-terminated polyphenyl ether grafted with a trifluoromethylated acrylate hydroxyl compound. The low-dielectric spherical ceramic powder polyphenyl ether composite dielectric material can effectively reduce the dielectric constant and dielectric loss, and has good interfacial compatibility and mechanical properties.

The invention provides a metal monatomic photocatalyst and a preparation method and application thereof, and the preparation method comprises the following steps: mixing a nitrogen-containing precursor and an ammonia water solution of a metal precursor, evaporating and roasting to obtain metal-loaded polymer carbon nitride powder; and mixing the powder with a lithium salt and a potassium salt, and roasting in vacuum to obtain the metal monatomic catalyst with optical activity. The metal monatomic catalyst prepared by the preparation method disclosed by the invention is used for photocatalytic carbon-nitrogen coupling reaction, trifluoromethylation reaction, cyanation reaction and cyano trifluoromethylation reaction, and good yield can be obtained. The catalyst is simple to prepare and wide in application range, and can better meet the requirements of the actual production process.

The application belongs to the field of catalytic chemistry, and particularly relates to a 1,10-phenanthroline ligand derivative, and preparation and application thereof. The application provides a derivative of a 1,10-phenanthroline ligand as shown in formula (I) with an amide group introduced at positions 2 and 9. The 1,10-phenanthroline ligand derivative with an amide group introduced at positions 2 and 9 can enhance metal coordination ability, optimize chelation stability with metals, and can be used as a high-efficiency metal catalyst ligand to catalyze organic reactions. The 1,10-phenanthroline ligand derivative can form stable metal coordination with transition metals such as iron, cobalt and nickel, and can efficiently catalyze trifluoromethylation reaction, Ullmann type etherification reaction and polymeric ester polymerization in cooperation with copper and zirconium alkoxide.

The invention provides a preparation method of 2-methyl-3-(trifluoromethyl) aniline and flunixin meglumine, which comprises the following steps: taking 3, 4, 5-trichlorotoluene as a raw material, and carrying out trichloromethylation reaction under the action of a first catalyst to obtain a trichloromethylation intermediate; carrying out halogen exchange reaction on the trichloromethylation intermediate under the action of a fluorinating agent to obtain a trifluoromethylation intermediate; carrying out nitration reaction on the trifluoromethylation intermediate under the action of a nitration reagent to obtain a nitration intermediate; and carrying out hydrogenation reduction reaction on the nitration intermediate under the action of a reducing agent and a second catalyst to obtain 2-methyl-3-(trifluoromethyl) aniline. According to the invention, 3, 4, 5-trichlorotoluene is taken as a starting raw material, the selectivity of trichloromethylation reaction is obviously improved, so that the yield of 2-methyl-3-(trifluoromethyl) aniline can be improved, and the method has the advantages of high selectivity, few byproducts, low cost and the like.

The present invention relates to a fluorosulfonyl difluoroacetic acid metal salt complex and its preparation method and application. The chemical formula is: L n M(O2CCF2SO2F) z The ligand L is selected from one of the following compounds: #imgabs0# wherein R1, R2, and R3 are each selected from hydrogen, alkyl, alkoxy, hydroxyl, carboxyl, ester, aryl, nitro, sulfonic acid, fluoroalkyl, or halogen; and the metal ion M is at least one of lithium, magnesium, calcium, strontium, barium, scandium, yttrium, titanium, zirconium, chromium, molybdenum, tungsten, iron, ruthenium, cobalt, rhodium, iridium, nickel, palladium, platinum, copper, silver, gold, zinc, cadmium, mercury, aluminum, indium, tin, lead, antimony, bismuth, manganese, sodium, or cesium. Compared with the prior art, the present invention has inexpensive and readily available starting materials, mild reaction conditions, simple post-processing, high yield, and the product can be used as a trifluoromethylation reagent, showing broad application prospects.

The application discloses a 2-trifluoromethyl-3-amino indole compound and a preparation method thereof, and belongs to the technical field of organic synthesis. The preparation method of the 2-trifluoromethyl-3-amino indole compound comprises the following steps: under the action of visible light induction and a tertiary amine organic base, free radical cascade cyclization reaction of CF3Br and an aryl isonitrile derivative is carried out in an organic solvent to obtain the 2-trifluoromethyl-3-amino indole compound. The application firstly proposes a method for preparing the 2-trifluoromethyl-3-amino indole compound in one step, which uses the aryl isonitrile derivative as a raw material, uses CF3Br as a trifluoromethylating reagent, and under the action of visible light induction and the tertiary amine organic base, free radical cascade cyclization reaction of trifluorobromomethane and the aryl isonitrile derivative is carried out. The raw material is cheap and easy to obtain, no noble metal photosensitizer needs to be added, the operation is simple, the reaction condition is mild, the reaction is green and safe, the reaction yield is good and the like, and the method has good application value.

This invention discloses a method for synthesizing heteroaryl trifluoromethyl compounds. The method involves mixing a heteroaryl iodide, a catalyst, and a trifluoromethylating agent, followed by a trifluoromethylation reaction. This invention proposes a method for generating heteroaryl trifluoromethyl compounds by reacting a heteroaryl iodide with sodium trifluoromethanesulfonate under copper catalysis. The copper powder and sodium trifluoromethanesulfonate used in this method are inexpensive, the reaction system has low moisture requirements, the reaction operation is simple, no byproducts are generated, post-processing is simple, and it exhibits good substrate compatibility, making it suitable for industrial-scale production.

The invention belongs to the technical field of organic synthesis, and particularly relates to a trifluoromethylated pyrazolone compound, a synthesis method and application. According to the preparation method, sodium trifluoromethanesulfinate and an acylhydrazone compound are used as raw materials, tetrabutyl ammonium hexafluorophosphate is used as an electrolyte, and the pyrazolone compound with a potential corrosion inhibition effect and a medical application prospect is synthesized at room temperature in a nitrogen atmosphere. Compared with a previously reported synthesis method, the method has the advantages of greenness, environmental protection, safety, high efficiency and energy conservation, the substrate application range is wide, the functional group compatibility is good, the raw materials are easy to obtain, and the operation is simple and convenient.

The present invention relates to a method for difunctionalizing olefins and delta-trifluoromethyl ketone products prepared thereby. The present invention provides a green mechanochemical approach for difunctionalizing unactivated olefins via a cascade radical trifluoromethylation / distal migration pathway. The present invention enables rapid modification of unactivated olefins via cascade reduction under mechanical redox conditions. Compared with photocatalysis and electrocatalysis, this method offers significant advantages, such as ease of operation, air compatibility, low solvent consumption, and catalyst recyclability, meeting the requirements of green chemistry.

The invention discloses a preparation method of a trifluoromethylated aromatic hydrocarbon compound, which is characterized in that in a system taking a water phase as a solvent, an aromatic hydrocarbon compound reacts with a trifluoromethyl reagent in the presence of an oxidizing agent and ferric salt to obtain the trifluoromethylated aromatic hydrocarbon compound. The water phase is used as a solvent, so that the use of an organic solvent is reduced, the problems of flammability, explosion, toxicity and the like are effectively prevented, the safety is improved, the resources are rich, and the cost is low; in addition, the method is mild in reaction condition, low in energy consumption and high in product yield, and meets production requirements.