22 results about "Bromobenzoic Acids" patented technology

The invention belongs to the field of preparation of halogen-containing substituted benzoic acid, and particularly relates to a method for preparing o-chlorobenzoic acid through hydrogenation selective debromination. According to the invention, hydrogen is used as a reducing agent, a palladium catalyst is used as a catalyst, a methanol aqueous solution is used as a solvent, and 2-chloro-3-bromobenzoic acid, 2-chloro-5-bromobenzoic acid or a mixture thereof are used as raw materials to prepare o-chlorobenzoic acid. According to the method, debromination is controlled through selective hydrogenation instead of dechlorination, so that generation of a byproduct benzoic acid is inhibited. The scheme is reasonable in design, simple in process and mild in reaction condition, and a new thought is provided for the synthesis method of o-chlorobenzoic acid.

A preparation method of the acene 1, 8-naphthalimide derivative comprises the steps that acene 1, 8-naphthalimide is added into a dichloromethane solvent, p-bromobenzoic acid, 1-ethyl-(3-dimethylaminopropyl) carbodiimide hydrochloride and 4-dimethylaminopyridine are sequentially added, stirring is carried out, and the acene 1, 8-naphthalimide derivative is obtained. Fully stirring and reacting the reaction mixture at 40-50 DEG C for 10-12 hours to obtain a reaction solution 2; and carrying out ice water quenching, suction filtration, extraction, drying and rotary evaporation on the reaction liquid 2 to obtain a solid product, and carrying out column chromatography purification to obtain the compound acene 1, 8-naphthalimide derivative. The preparation method of the phosphorescent material is simple and convenient, compared with a noble metal phosphorescent system, the cost is low, the synthesis method of the guest phosphorescent dye is simple, the yield is high, the phosphorescent effect is obvious, and the phosphorescent phenomenon is stable, so that the application potential in the fields of phosphorescent anti-counterfeiting and the like is huge.

This invention discloses a catalyst for the production of p-cyanobenzoic acid and its preparation method, belonging to the field of catalyst technology. The method includes the following steps: adding an organic ligand solution dropwise to a cobalt source, stirring, aging, centrifuging, collecting the solid phase and washing to obtain a cobalt-based MOF framework; dispersing the cobalt-based MOF framework in a copper source, stirring, filtering, and collecting the solid phase to obtain copper-cobalt doped particles; dispersing reduced graphene oxide in deionized water, adding sodium alginate, stirring evenly, adding copper-cobalt doped particles and ammonium dihydrogen phosphate, continuing stirring, standing, centrifuging, collecting the lower gel precipitate, washing, and vacuum freeze-drying to obtain an aerogel precursor; carbonizing the aerogel precursor in a hydrogen-argon mixed atmosphere, cooling, and grinding to obtain the catalyst. The catalyst prepared by this invention can efficiently catalyze the cyanation reaction of p-bromobenzoic acid, improving the yield and purity of the target product, while also possessing excellent recycling performance.

The invention discloses a synthesis method of 4-bromo-3-(ethoxymethyl) benzoic acid, which comprises the following steps: (1) activating carboxyl of p-bromobenzoic acid serving as a raw material in the presence of an organic anhydride activator, and then performing chloromethylation reaction with paraformaldehyde in the presence of a chlorine-containing Lewis acid catalyst to obtain 4-bromo-3-(ethoxymethyl) benzoic acid; after the reaction is completed, carrying out post-treatment to obtain an intermediate 4-bromo-3-(chloromethyl) benzoic acid; and (2) carrying out nucleophilic substitution reaction on the intermediate obtained in the step (1) in ethanol under the action of inorganic alkali to prepare the target product 4-bromo-3-(ethoxymethyl) benzoic acid. According to the invention, through one-pot activation and chloromethylation of p-bromobenzoic acid, concise, efficient and highly economical synthesis from cheap raw materials to the sparsentan key intermediate is realized.

The invention discloses a synthesis method of a Vinetoram key intermediate and Vinetoram, and relates to the technical field of organic synthesis.The synthesis method comprises the steps that 1-((4 '-chloro-5, 5-dimethyl-3, 4, 5, 6-tetrahydro-[1, 1'-biphenyl]-2-yl) methyl) piperazine hydrochloride and 2-((1H-pyrrolo [2, 3-b] pyridine-5-yl) oxy)-4-bromobenzoic acid methyl ester are used as reaction raw materials, a reaction is carried out, and the Vinetoram key intermediate and the synthesis method of the Vinetoram key intermediate are synthesized; the method comprises the following steps: carrying out a substitution reaction and a hydrolysis reaction to obtain a key intermediate of the Venotocork, and carrying out a condensation reaction on the intermediate and 3-nitro-4-((tetrahydro-2H-pyran-4-yl) methylamino) benzenesulfonamide to obtain the Venotocork. The synthesis method has the advantages of short process route, easily available raw materials, mild reaction conditions, high yield and purity of the intermediate and the Vinetoram, facilitation of the improvement of the yield and quality of the Vinetoram, and reduction of the production cost of the Vinetoram.

This invention discloses a synthetic process for an empagliflozin intermediate, belonging to the technical field of pharmaceutical intermediate synthesis. The synthetic process is as follows: 2-chloro-5-bromobenzoic acid is first mixed with dichloromethane and N,N-dimethylformamide, and thionyl chloride is added dropwise to obtain a dichloromethane solution of acyl chloride. Then, it is reacted with fluorobenzene under anhydrous aluminum trichloride catalysis to obtain intermediate EGAB-3. Then, it is dehydrated by azeotropic reaction with potassium hydroxide aqueous solution in toluene, and then refluxed with 3-hydroxytetrahydrofuran under tetrabutylammonium bromide catalysis to obtain intermediate EGAB-7. Then, it is reacted with 1,1,3,3-tetramethyldisiloxane under anhydrous aluminum trichloride and nitrogen protection, dried, and tested to be qualified to obtain empagliflozin intermediate. This process achieves high purity, high yield, and low isomer impurities in the preparation of empagliflozin intermediate.

The invention discloses a dapagliflozin intermediate synthesis method and application, and the dapagliflozin intermediate synthesis method comprises the following steps: heating 2-chloro-5-bromobenzoic acid, 1, 2-dichloroethane, bis (trichloromethyl) carbonate and a catalyst for reflux reaction, and cooling to obtain a 2-chloro-5-bromobenzoyl chloride solution; the preparation method comprises the following steps: mixing phenetole, 1, 2-dichloroethane and aluminum trichloride, stirring, and dropwise adding a 2-chloro-5-bromobenzoyl chloride solution to obtain 2-chloro-5-bromo-4 '-ethoxybenzophenone; and synthesizing the 4-bromine-2-chloro-2-(4-ethoxybenzyl) benzene. According to the method, the cheap BTC is used as an acylating chlorination reagent, so that the reagent cost is greatly reduced, the dosage of NaBH4 and AlCl3 in carbonyl reduction is reduced, the reagent cost and the amount of three wastes in the industry are further reduced, a foundation is laid for industrial production of the dapagliflozin intermediate, the yield is relatively high after each step of reaction, and the production cost of an enterprise is reduced.

The invention relates to a method for detecting the content of quasi-binary brominated alcohol in electronic waste recycled materials, which comprises the following steps: (1) mixing a quasi-binary brominated alcohol standard substance with a solvent to prepare a standard working solution; the method comprises the following steps: extracting binary-like brominated alcohol in the electronic waste recovered material, and preparing a to-be-detected sample solution; and (2) carrying out ultra-high performance liquid chromatography-mass spectrometry detection analysis on the standard working solution and the to-be-detected sample solution obtained in the step (1), and calculating according to a standard curve to obtain the content of the binary bromohydrin-like in the electronic waste recycled material, the binary bromo-alcohol-like compound comprises 2, 2-bis (bromomethyl)-1, 3-propylene glycol and / or diisooctyl ester-2, 3, 4, 5-tetrabromobenzoic acid, and the diisooctyl ester-2, 3, 4, 5-tetrabromobenzoic acid is used as a catalyst. The detection method provided by the invention can be used for effectively detecting the content of the similar binary bromo-alcohol in the electronic waste recycled material, and the detection method is simple and rapid, low in detection limit, strong in matrix interference resistance, sensitive and accurate, and excellent in repeatability and reproducibility.

The invention provides 3-bromo-9-(4-chlorphenyl)-9-phenyl-9H-fluorene and a preparation method thereof, and relates to the technical field of preparation of organic compound materials. According to the present invention, 2-amino-4-bromobenzoic acid is adopted as an initial raw material to prepare the 3-bromo-9-(4-chlorphenyl)-9-phenyl-9H-fluorene; the preparation method disclosed by the invention is simple, few in impurities, few in waste materials and convenient for industrial mass production.

The application belongs to the field of medicine and chemical industry, and particularly relates to a preparation method of ketoprofen. 3-bromobenzoic acid is used as a starting material, and a chlorination reaction is carried out with thionyl chloride. Then, a Friedel-Crafts reaction is carried out with benzene under the catalysis of aluminum chloride. The reaction product is subjected to a Friedel-Crafts reaction with ethylene, an addition reaction with hydrobromic acid, a reaction with a cyanating agent, and then hydrolysis under the action of an acid, so as to obtain ketoprofen. The application provides a reasonable reaction route, realizes the preparation of ketoprofen by using cheap and readily available and green and environmentally-friendly reagents, avoids the use of highly corrosive, highly toxic, flammable and expensive reagents, has low requirements on equipment, reduces the operation difficulty and the burden of post-reaction treatment, and reduces the cost. The application is a simple, green and economic process route for preparing ketoprofen, the obtained product has high yield and good purity, and is suitable for industrial mass production of ketoprofen.

The present invention belongs to the field of materials / photoresists and relates to an "isotropic" zinc-based hybrid compound, a preparation method thereof, and an application in photoresists, so as to solve the problem of decreased film-forming properties of zinc-based hybrid compounds with a single structure in the prepared photoresist. The compound is prepared in one step using p-bromobenzoic acid and zinc acetate dihydrate as raw materials, has a molecular formula of C9H9BrO5Zn, belongs to the orthorhombic system, has a space group of Pna21, and has a unit cell length, width, and height of 8.0560(7)Å, 5.7165(6)Å, and 25.226(2)Å, respectively; α=β=γ=90°. The compound can be directly used as the sole component and mixed with an organic solvent to prepare an "isotropic" zinc-based hybrid photoresist film, and the photoresist film can be used in the field of membrane science or photolithography. The compound has good stability, and the photoresist film has good solubility, film-forming properties, adhesion, thermal stability, is easy to store, and has a stable structure.

The present invention relates to a method for the rapid synthesis of 2-hydroxyacridone by an ultrasonic-assisted one-pot method. 2-Bromobenzoic acid is dissolved in DMF to form solution A, and p-methoxyaniline is dissolved in DMF to form solution B. Copper powder is added as a catalyst in a reaction vessel, and then solution A and solution B are added thereto. The resulting reaction mixture is placed in an ultrasonic reactor, and the reaction is assisted by ultrasound for 45-60 min. After cooling, distillation is carried out under reduced pressure, and then hot water is added to extract the product. The crude 2-hydroxyacridone obtained is purified by recrystallization with ethanol to obtain high-purity 2-hydroxyacridone. The present invention rapidly, efficiently and with high yield prepares the target product 2-hydroxyacridone by an ultrasonic-assisted one-pot method at a reaction temperature of about 50 °C. The process steps are simple, the operation is convenient, the reaction time is short, the reaction conditions are mild, the raw materials are easily available, the yield is high, the loss of raw materials is greatly reduced, the reaction time is shortened, and the reaction energy consumption is reduced.

This invention discloses a method for synthesizing bromhexine hydrochloride, with the following specific steps: Step (1), using 2-amino-3,5-dibromobenzoic acid as a raw material, reacting it with trimethylacetyl chloride via an anhydride method under the action of an acid-binding agent to obtain compound 2-amino-3,5-dibromobenzoic acid anhydride; Step (2), the 2-amino-3,5-dibromobenzoic acid anhydride obtained in Step 1 undergoes nucleophilic addition with N-methylcyclohexylamine to obtain compound 5, bromhexine hydrochloride intermediate; Step (3), the above compound 5, bromhexine hydrochloride intermediate undergoes amide reduction and salt formation reaction to obtain bromhexine hydrochloride. This process provides a new route for preparing bromhexine hydrochloride, avoiding the heavily regulated chlorination process, reducing the release of toxic gases from strong halogen reagents such as thionyl chloride, significantly reducing safety risks and environmental protection investment, and the reaction itself is safe and fast, which is conducive to industrial production.

The present invention relates to a copper complex containing an ortho-carborane Schiff base ligand, a preparation method, and an application thereof. The chemical structural formula of the copper complex is: #imgabs0#, wherein "·" represents a boron-hydrogen bond, and Ar represents any one of phenyl, 4-methoxyphenyl, 4-bromophenyl, 4-nitrophenyl, or 2-pyridyl. The preparation method comprises the following steps: 1) dissolving ortho-carborane dicarboxaldehyde and aromatic amine in an organic solvent, reacting to obtain a mixed solvent; 2) adding CuBr2 to the mixed solvent, reacting, and separating to obtain a copper complex. The copper complex is used as a catalyst for catalytic synthesis of isoindolinone and its derivatives. Compared with the prior art, the present invention adopts a one-pot process to obtain a copper complex containing an ortho-carborane Schiff base ligand. The synthesis method has excellent selectivity and high yield. The obtained copper complex can catalyze the reaction of 2-bromobenzoic acid, terminal alkynes, and primary amines to synthesize isoindolinone derivatives at room temperature, with high reaction efficiency and environmental friendliness.

The invention belongs to the field of marine food safety and sewage treatment, and particularly relates to application of a carboxyl functionalized microporous organic network to removal of methylamine, dimethylamine and trimethylamine in euphausia superba oil, fish oil and wastewater. The preparation method of the carboxyl-functionalized microporous organic network comprises the following steps that a catalyst is dispersed in an organic solvent, then a reaction monomer 1 and a monomer 2 are added, the monomer 1 is 1, 3, 5-tris (4-acetylene phenyl) alkyne, the monomer 2 is at least one of 2, 5-dibromoterephthalic acid, 2, 5-dibromobenzoic acid and 3, 6-dibromophenyl-1, 2, 4, 5-tetracarboxylic acid, and the catalyst is at least one of 2, 5-dibromoterephthalic acid, 2, 5-dibromobenzoic acid and 3, 6-dibromophenyl-1, 2, 4, 5-tetracarboxylic acid. Reacting after dispersing; and after the reaction is finished and the temperature is reduced to room temperature, filtering and collecting solids, washing and drying to obtain the carboxyl MON. The carboxyl sites in the material can form strong electrostatic interaction and hydrogen-bond interaction with molecules such as TMA, so that the adsorption selectivity and the bonding strength are remarkably improved.

The present invention discloses a waterproof and anti-radiation lens and a preparation method thereof, relating to the technical field of lenses. In the present invention, a nano-sheet carbon film is deposited, and carbon nanotubes are vertically grown and connected in series to form a conductive network, thereby forming a conductive loss of electromagnetic radiation. Then, a magnetic layer and a non-magnetic layer are sequentially deposited to form an anti-radiation layer. While preventing water fog, a magnetic absorption network can be formed to promote magnetic loss and improve the anti-radiation ability of the lens. Moreover, the existence of multiple interfaces accelerates the conversion of electromagnetic waves into heat energy, improving the anti-radiation and waterproof fog properties of the lens. Then, the anti-radiation layer is modified with hexamethylenediamine methyltrimethoxysilane, 2-amino-3-chloro-6-bromobenzoic acid, cinnamitrile, dimethylaminopropylamine, and (3S)-3-amino-N-cyclohexyl-2-oxohexanamide to effectively absorb blue light and achieve the effect of filtering blue light. The waterproof and anti-radiation lens prepared by the present invention has the effects of preventing water fog, anti-radiation, and filtering blue light.

This invention belongs to the field of organic synthesis technology and provides a method for preparing a key intermediate of ambroxol hydrochloride. The method includes the following steps: methyl 2-aminobenzoate reacts with a brominating reagent under the action of an initiator to generate methyl 2-amino-3,5-dibromobenzoate via a bromination reaction; subsequently, methyl 2-amino-3,5-dibromobenzoate is reduced to 2-amino-3,5-dibromobenzyl alcohol in a reduction system; finally, under the action of an oxidizing agent, 2-amino-3,5-dibromobenzyl alcohol is further oxidized to form the target compound 2-amino-3,5-dibromobenzaldehyde. The optimized process has mild reaction conditions, conforms to green and environmentally friendly principles, significantly improves route safety, uses inexpensive and readily available raw materials, and achieves high product yield and purity, making it suitable for industrial production.

The present invention belongs to the technical field of compound preparation, and particularly relates to a preparation method of 2-amino-4-bromo-5-chlorobenzoic acid, which includes S1, nitrating p-toluidine in a sulfuric acid system to generate a nitrating solution; S2, synthesizing 2-nitro-4-bromotoluene; S3, synthesizing 2-amino-4-bromotoluene; S4, synthesizing 2-acetamido-4-bromotoluene; S5, synthesizing 2-acetamido-4-bromobenzoic acid; S6, synthesizing 2-amino-4-bromobenzoic acid; S7, synthesizing 2-acetamido-4-bromo-5-chlorobenzoic acid; S8, synthesizing 2-amino-4-bromo-5-chlorobenzoic acid. The beneficial effects of the present invention are that the cost is controllable, and the key intermediates can all be sold as products; almost no laborious purification is required for each step; no solvent is used throughout the process, and the generated wastewater, except for the diazotization wastewater, has extremely high biodegradability, which is very beneficial to the biochemical treatment in the sewage treatment station.

The invention discloses a method for synthesizing phenanthridinone compounds by palladium catalysis, the method is in an organic solvent system, using 2 bromobenzamide compounds and o-bromobenzoic acid as raw materials, using metal palladium salt as catalyst, adding alkali and ligand stirring reaction, after reacting completely under the conditions of 100~120 DEG C, phenanthridinone compounds are obtained after reaction solution post-processing. The present invention selects o-halobenzoic acid as raw material, using metal palladium salt as catalyst, constructs optimal reaction system, Pd catalyzes 2 bromobenzamides and o-bromobenzoic acid by palladium association benzene intermolecular [4+2] cyclization reaction, provides a kind of modular method of phenanthridinone skeleton conveniently. The method is prepared using one-pot method, and raw materials are easy to obtain, and reaction conditions are mild, and system is green and environmentally friendly, and product is easily separated and purified, and highly purified phenanthridinone compounds can be obtained efficiently and in high yield.

The invention discloses a montelukast intermediate synthesis method, and relates to the technical field of chemical synthetic drug intermediates, in the presence of a solvent, in the presence of an alkali and under the catalysis of a nickel catalyst NiBr2 (acac) L, methyl o-bromobenzoate and (E)-1-(3-(2-(7-chloroquinoline-2-yl) vinyl) phenyl) propyl-2-ene-1-one (MK2) are subjected to a coupling reaction, and the montelukast intermediate is obtained. Synthesizing a montelukast sodium intermediate; the novel nickel catalyst NiBr2 (acac) L is adopted, coupling of olefin and halogen at low temperature and pressure is achieved, and the method has great significance for reducing the reaction cost and being suitable for large-scale industrial production.

This invention belongs to the field of preparation of halogenated substituted benzoic acids, specifically relating to a method for selectively debrominating o-chlorobenzoic acid via hydrogenation. The invention uses hydrogen as a reducing agent, palladium as a catalyst, and methanol-water solution as a solvent, with 2-chloro-3-bromobenzoic acid, 2-chloro-5-bromobenzoic acid, or mixtures thereof as raw materials to prepare o-chlorobenzoic acid. This invention controls debromination through selective hydrogenation without dechlorination, suppressing the formation of the byproduct benzoic acid. This scheme is rationally designed, simple in process, and operates under mild reaction conditions, providing a new approach for the synthesis of o-chlorobenzoic acid.

The invention discloses a preparation method of a water-mist-proof and radiation-proof lens, and relates to the technical field of lenses. The nano-sheet carbon film is deposited, the carbon nanotubes vertically grow and are connected in series to form a conductive network, conductive loss of electromagnetic radiation is formed, then the magnetic layer and the non-magnetic layer are sequentially deposited, the anti-radiation layer is formed, water mist is prevented, meanwhile, a magnetic absorption network can be formed, magnetic loss is promoted, and the anti-radiation capacity of the lens is improved; according to the lens, the anti-radiation layer is arranged on the surface of the lens, electromagnetic waves are accelerated to be converted into heat energy due to the existence of multiple interfaces, the anti-radiation performance and the water mist resistance of the lens are improved, and then the anti-radiation layer is modified by hexamethylenediamine methyl trimethoxy silane, 2-amino-3-chloro-6-bromobenzoic acid, cinnamyl nitrile, dimethylaminopropylamine and (3S)-3-amino-N-cyclohexyl-2-oxohexanamide in sequence, so that blue light is effectively absorbed, and the anti-radiation performance of the lens is improved. And the blue light filtering effect is achieved. The water-mist-proof and radiation-proof lens prepared by the invention has water-mist-proof, radiation-proof and blue-light-proof effects.