21 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 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 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 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.

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 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.

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 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.

The present application relates to a kind of electrochemical synthesis method of fluorine-containing and trifluoromethyl compound, which uses cheap chemical olefin, trifluoromethyl sulfinic acid salt and triethylamine trifluoride as raw material, carries out catalytic fluorination of olefin, trifluoromethylation without exogenous oxidant and transition metal, synthesizes fluorine-containing and trifluoromethyl compound, provides active molecule with atom economy, step simplicity, low price and wide application range High efficiency, green and environmentally friendly synthesis route, to meet the requirements of industrial application, the synthesis method of the present application is more green, environment-friendly and wide application range.

The application provides a preparation method of 4-trifluoromethylaniline, comprising the following steps: introducing ammonia into a raw material system comprising 4-chlorobenzotrifluoride, formaldehyde and a dehydrating agent to perform a first reaction; after the 4-chlorobenzotrifluoride is completely converted, the introduction of ammonia is stopped, and a dilute acid solution is added to the reaction system to perform a second reaction, thereby obtaining 4-trifluoromethylaniline. The preparation method of 4-trifluoromethylaniline provided by the application does not need to use expensive copper salt catalysts and trifluoromethylation reagents, and 4-trifluoromethylaniline can be prepared in a high yield by one-pot method with low-cost 4-trifluoromethylaniline as a raw material, thereby greatly reducing the preparation cost.

This invention discloses a method for the trifluoromethylation of olefins, comprising: reacting an olefin, a trifluoromethylating agent, and hydroxylamine in a solvent to obtain a trifluoromethylated olefin product. The method of this invention uses hydroxylamine as an initiator, and under mild conditions, nonmetals promote the trifluoromethylation of the olefin.

The invention discloses a synthetic method of an enzalutamide intermediate 4-amino-2-trifluoromethyl benzonitrile, which comprises the following steps: by taking a compound in a formula (II) as a raw material, dissolving the compound in a solvent A together with a free radical source A, a free radical initiator A and a photocatalyst A, and reacting under an illumination condition to obtain a compound III; mixing the compound (III) with acetic acid and tert-butyl nitrite, reacting in the absence of a solvent or a solvent B, and then adding tert-butyl isonitrile for reacting to obtain a compound (IV); and dissolving the compound (IV), a ligand C, organic alkali and nickel hexammine chloride in a solvent C, and reacting under the illumination condition to obtain the target product 4-amino-2-trifluoromethyl benzonitrile as shown in the formula (I). The reaction process is as follows: the substituent X in the formula is chlorine or bromine. According to the method, 4-bromoaniline or 4-chloro-aniline which is low in price and easy to obtain is taken as a starting raw material, and trifluoromethyl is directly introduced into a benzene ring by adopting photocatalytic free radical trifluoromethylation, so that the method conforms to the green chemical principle, and amino protection and deprotection steps are avoided.

The application discloses a synthesis method of 3,6-di(trifluoromethyl)-pyromellitic dianhydride. The synthesis method comprises the following steps: 1,2,4,5-tetramethylbenzene is subjected to iodization reaction in the presence of iodine, persulfate, concentrated sulfuric acid and acetic acid to obtain 3,6-diiodotetramethylbenzene; 3,6-diiodotetramethylbenzene is subjected to trifluoromethylation reaction with TMSCF3 (trifluoromethyltrimethylsilane) in the presence of CuX and MF in a polar solvent to obtain 3,6-di(trifluoromethyl)-tetramethylbenzene; 3,6-diiodotetramethylbenzene and an oxidant are subjected to oxidation reaction to obtain 3,6-di(trifluoromethyl)-pyromellitic acid; and 3,6-di(trifluoromethyl)-pyromellitic acid is subjected to dehydration and cyclization with acetic anhydride to obtain 3,6-di(trifluoromethyl)-pyromellitic dianhydrate. The reaction condition of the application is relatively mild, the treatment is simple, the efficiency is relatively high, and the cost is relatively low.

The application relates to a method for directly trifluoromethylating aniline compounds to synthesize trifluoromethylaniline derivatives by using visible light catalysis. A tetradentate platinum (II) complex Pt (1-ptz) is used as a photocatalyst, Umemoto reagent or Langlois reagent (CF3SO2Na) is used as a trifluoromethyl source, and direct trifluoromethylation of aniline compounds is realized under visible light irradiation. The reaction does not need to use an oxidation-reduction reagent, and naked amino groups are not needed to be protected, and meanwhile, photocatalyst recycling and reuse are realized.

The application provides an E-type beta-trifluoromethyl enamide compound, which has a structure shown in formula (I), an electrochemical oxidation synthesis method, which comprises the following steps: stirring and mixing non-cyclic enamide compounds, trifluoromethyl sulfinic acid salts, additives and solvents in a reactor equipped with electrode sheets, and performing beta-C(sp 2 )-H trifluoromethylation reaction under electrochemical conditions, so that a series of E-type beta-trifluoromethyl enamide compounds are obtained with high selectivity. The application uses electric current as an oxidant, does not need to add electrolytes, and does not need to add various metal catalysts and chemical oxidants. The reaction condition is mild, the substrate universality is wide, and the functional group tolerance is good. The application is simple and easy to implement, the reaction system is simple, and the pollution is small, which meets the green chemistry concept and has good application potential.

The application discloses a trifluoromethyl-containing polyurethane material and a preparation method and application thereof. Trifluoromethyl TDI is obtained by introducing trifluoromethyl into TDI, and is polymerized with different double-hydroxyl-containing polymers to prepare a polyurethane material. The mechanical properties of the polyurethane are effectively improved through trifluoromethylation, thereby prolonging the service life of the polyurethane. The polyurethane prepared by the application has higher tensile strength, higher toughness, good uniformity, excellent comprehensive performance, higher reliability and longer service life than TDI, and has important significance and development value for widening the application of the polyurethane material in the fields of aerospace, automobiles, textiles, buildings, medical treatment, intelligent detection and the like.

The invention relates to a method for preparing a quinoxalinone trifluoromethylation product. The method comprises the following steps: in an inert gas atmosphere, adding a quinoxaline ketone compound, 4-(dimethylamino)-1-((trifluoromethyl) sulfonyl) pyridine-1-trifluoromethanesulfonic acid onium, alkali and a photosensitizer into a solvent, reacting for 10-12 hours at the temperature of 10-30 DEG C under blue light irradiation, and separating and purifying through column chromatography to obtain the quinoxaline ketone compound. And finally, obtaining the quinoxaline ketone compound substituted by the trifluoromethyl at the C3 position. The preparation conditions are mild, no heavy metal is left, only column chromatography separation is needed, and post-treatment is simple.