92 results about "Bromobenzoic Acids" patented technology

The invention provides a synthesis method of 5-bromo-2-chloro benzoic acid.The method includes the following steps of A, making 2-chlorine benzotrichloride and bromide reagents react under the effect of a catalyst to obtain 2-chloro-5-bromine benzotrichloride, wherein bromide reagents include one or more of bromine, N-bromosuccinimide, dibromohydantoin and hydrobromic acid; B, conducting hydrolysis reaction on 2-chloro-5-bromine benzotrichloride in the step A under the acid condition to obtain 5-bromo-2-chloro benzoic acid.According to the method, 2-chlorine benzotrichloride which is low in price and easy to obtain is adopted as the raw material, operation is easy, intermediates do not need to be purified, 5-bromo-2-chloro benzoic acid is synthesized through a one-pot method, purity is high, yield is high, three-waste emission is little, and production cost is low.It is shown through experiment results that 2-chloro-5-benzoic acid obtained according to the synthesis method has yield larger than 95% and purity of 80-92%.

The invention relates to a preparation method of 2-(5-bromo-2-methylbenzyl)-5-(4-fluorophenyl)thiophene, which comprises the following steps: carrying out coupling reaction on 2-bromothiophene and p-bromofluorobenzene to obtain 2-(4-fluorophenyl)thiophene; carrying out Friedel-Craft reaction on the 2-(4-fluorophenyl)thiophene and 2-methyl-5-bromobenzoic acid to obtain 5-bromo-2-methylphenyl-2-(4-fluorophenyl)thienyl ketone; and finally, carrying out reduction reaction on the 5-bromo-2-methylphenyl-2-(4-fluorophenyl)thienyl ketone to obtain the 2-(5-bromo-2-methylbenzyl)-5-(4-fluorophenyl)thiophene. By using the cheap and accessible p-bromofluorobenzene and 2-methyl-5-bromobenzoic acid as the raw materials for synthesizing the canagliflozin intermediate, the product is easy for purification, and the method is simple to operate and has the advantages of low cost and environment friendliness.

The invention discloses a preparation method of 4-chloro-3-(4-ethoxybenzyl)benzaldehyde. The preparation method comprises the following steps that 2-chloro-5-bromobenzoic acid is dissolved in an organic solvent, an acylating chlorination reagent is added into the solution, the mixed solution undergoes a reaction to produce 5-bromo-2-chlorobenzoyl chloride, 5-bromo-2-chlorobenzoyl chloride is dissolved in an organic solvent, the solution is cooled, the cooled solution is added with phenetole and acid catalysts, the mixed solution undergoes a reaction to produce (5-bromo-2-chlorphenyl)(4-ethoxyphenyl)ketone, (5-bromo-2-chlorphenyl)(4-ethoxyphenyl)ketone is dissolved in an organic solvent, the solution is added with a reduction reagent system, the solution undergoes a reaction to produce 4-bromo-1-chloro-2-(4-ethoxybenzyl)benzene, 4-bromo-1-chloro-2-(4-ethoxybenzyl)benzene is dissolved in an organic solvent, a formylation reagent is added into the solution and the mixed solution undergoes a reaction to produce 4-chloro-3-(4-ethoxybenzyl)benzaldehyde. The preparation method utilizes cheap and easily available raw materials and reagents and has a simple synthesis route, simple processes and a high yield.

The invention relates to an intermediate of pemetrexed disodium, a preparation method thereof and a method for preparing pemetrexed disodium thereby; and the intermediate is (2-(4-(3-(2,4-diamino-6-oxy-1,6-dihydro-pyridine-5-group)-3-(1,3)dioxolane-2-group-propyl) benzylamine)sodium glutaric acid. The synthesis of the intermediate comprises the following steps: firstly, condensation reaction is conducted on 4-bromobenzoic acid or 4-iodobenzoic acid and L-glutamate diethylester, then Hack reaction is conducted, 4-bromo is replaced and 4-butyraldehyde is formed, then selective bromo replacement is conducted and the 4-butyladehyde is converted into 2-bromobutyraldehyde, and then condensation reaction of aldehyde and ethylene glycol is utilized for protecting the aldehyde, and pyrimidine ring is further synthesized, and finally the intermediate is obtained. Acid hydrolysis ring-closing reaction and sodium hydroxide salification are respectively conducted for once on the intermediate so as to obtain the pemetrexed disodium. The method for preparing pemetrexed disodium in the invention has high yield, low cost and easy operation and is applicable to industrialized production.

The invention discloses a one-pot synthesis method for 5-bromo-2-chloro-4'-ethoxy diphenylmethane. The method comprises the following continuous steps of: taking 2-chloro-5-bromobenzoic acid as a raw material, reacting it with thionyl chloride to generate 2-chloro-5-bromobenzoyl chloride, and adding an organic solvent, Lewis acid, phenetole and borohydride to undergo Friedel-Crafts acylation reaction and hydroboration reduction reaction so as to obtain the 5-bromo-2-chloro-4'-ethoxy diphenylmethane. The process involved in the invention has the advantages that the same Lewis acid is used as a catalyst in the Friedel-Crafts acylation reaction and the hydroboration reduction reaction, so that the catalyst consumption is greatly reduced, the operation is simple, and the intermediate needs no separation and purification. By effectively controlling the reaction conditions, and the charging sequence and proportion, the 5-bromo-2-chloro-4'-ethoxy diphenylmethane can be synthesized by one step, and fewer three wastes are discharged, the solvent recovery effect is good, and the production cost is low.

The invention discloses a fluorescent probe capable of quickly detecting hydrogen sulfite ions and a preparation method and application thereof. The preparation method includes: taking beta-pinene oxidation derivative nopinone which is one of main ingredients of natural renewable natural resource turpentine as a raw material, and allowing Claisen condensation reaction with 4-methyl bromobenzoate to obtain 3-(4'-bromobenzoyl) nopinone; allowing 3-(4'-bromobenzoyl) nopinone to be in coupling reaction with 4-formylbenzeneboronic acid to obtain 3-(4''-formyl-1', 1''-biphenyl-4'-carbonyl) nopinone;allowing 3-(4''-formyl-1', 1''-biphenyl-4'-carbonyl) nopinone to react with boron trifluoride etherate to obtain a 3-(4''-formyl-1', 1''-biphenyl-4'-carbonyl) nopinone based fluoroboron complex. Thecompound serving as a high-selectivity high-sensitivity color ratio type fluorescent probe has good application in the aspect of detecting the hydrogen sulfite ions.

The invention discloses an acridine-1, 2, 3-triazole type compound and a preparation method and application thereof. The preparation method of the acridine-1, 2, 3-triazole type compound comprises the following steps: 1) performing ullmann reaction by taking o-bromobenzoic acid and p-methoxyaniline as raw materials, taking potassium carbonate and copper powder as catalysts and taking isoamyl alcohol or n-amyl alcohol as a solvent to obtain a compound 1; 2) cyclizing the compound 1 with phosphorus oxychloride to prepare a compound 2; 3) dissolving the compound 2 in DMF (dimethylformamide) and performing nucleophilic substitution reaction with sodium azide to prepare a compound 3; and 4) taking p-methoxyphenylacetylene, dissolving in a tert-butyl alcohol/water solution, adding vitamin C sodium, copper sulfate pentahydrate and the compound 3 to react, performing suction filtration, and recrystallizing for preparation. In-vitro anti-tumor test results show that the acridine-1, 2, 3-triazole type compound has significant in-vitro anti-tumor activity against three subjects, namely MGC80-3, BEL-7404 and T24, has relatively good potential medicinal values, and is expected to be used for preparing various anti-tumor medicines.

The invention relates to a method for preparing phenylboronic acid-2-methyl formate. A starting material is a commercial raw material on the market or easy-to-prepare bromobenzoic acid methyl ester; and under a condition of low temperature, n-butyl lithium is dripped into a mixture of the main raw material of bromobenzoic acid methyl ester and a boric acid ester compound to form the phenylboronic acid-2-methyl formate through hydrolysis. The method has the advantages of readily available raw materials, high reaction purity and yield, stable process conditions, simple operation and suitability for large-scale production and provides a new thought and means for preparing the phenylboronic acid-2-methyl formate.

The present invention relates to a 9-amino substituted pyrido acridine derivative, a preparation method and uses thereof, wherein the structure formula of the derivative is represented in the instruction. The preparation method comprises that 2-bromobenzoic acid and 8-amino quinoline are adopted to prepare N-(quinolyl)anthranilic acid, the product is subjected to cyclization with phosphorus oxychloride to obtain 9-chloro pyrido acridine, the 9-chloro pyrido acridine is dissolved in ethanol, and benzylamine is added to carry out a nucleophilic substitution reaction so as to prepare the target product. The derivative can be used as an acetylcholinesterase inhibitor so as to be used for the treatment of Alzheimer's disease, cerebrovascular dementia and other diseases.

The invention discloses a preparation method of p-carboxyphenylboronic acid. The preparation method comprises the steps of carrying out an amidation reaction on bromobenzoic acid and diisopropylamine to obtain a reaction intermediate 4-bromo-N,N-diisopropylbenzamide; carrying out the substitution reaction on the 4-bromo-N,N-diisopropylbenzamide at a reaction temperature ranging from -75 to -80 DEG C in a solvent which is dry tetrahydrofuran, thereby obtaining (4-(diisopropylcarbamyl)phenyl) boric acid; hydrolyzing (4-(diisopropylcarbamyl)phenyl) boric acid in the presence of lithium hydroxide monohydrate to obtain p-carboxyphenylboronic acid. The preparation method provided by the invention is high in product yield, simple and convenient to operate, low in reaction cost and applicable to industrial production.

The invention discloses a method for preparing 2-methyl-4-formaldoxime methyl benzoate. The method comprises the following steps: performing acylating chlorination on 2-methyl-4-bromobenzoic acid, carrying out methanol esterification and cyano substitution, and then performing nucleophilic addition elimination with hydroxylamine hydrochloride under alkaline conditions to obtain a target product. The method has the advantages that the process route is simple; reaction conditions are mild; the product yield is high; the total yield reaches 61 percent; the product quality is high; the appearance is white solid; the purity reaches 99.2 percent.

The invention discloses an acridine-1,2,4-triazole-5-thioketone compound and a preparation method and applications of the acridine-1,2,4-triazole-5-thioketone compound. The preparation method of the compound comprises the following steps: 1) by taking an o-bromobenzoic acid and p-methoxyaniline as raw materials, taking potassium carbonate and copper powder as catalysts, and taking isopentyl alcohol or n-amyl alcohol as a solvent, reacting so as to obtain a compound 1; 2) carrying out cyclization on the compound 1 by using phosphorus oxychloride so as to obtain a compound 2; 3) after the compound 2 is dissolved by using an organic solvent, in the presence of tetrabutylammonium bromide, reacting the dissolved compound 2 with sodium sulfocyanate so as to obtain a compound 3; 4) after the compound 3 is dissolved by using an organic solvent, reacting the dissolved compound 3 with m-nitrobenzoylhydrazine so as to obtain a compound 4; and 5) reacting the compound 4 with sodium carbonate, carrying out suction filtration on a reactant, collecting filter liquor, adjusting the pH value of the filter liquor to be less than 4, separating out precipitates, and carrying out suction filtration on the precipitates. In-vitro antitumor test results show that the compound has a significant in-vitro antitumor activity to tested MGC80-3, NCI-H460 and T24.

The invention relates to a method for preparing 4-bromobenzoic acid and belongs to the technical field of compound production and preparation. The method comprises the following steps: by taking bromotoluene as an initial raw material, glacial acetic acid as a solvent and oxygen as an oxidant, carrying out catalytic oxidation on parabromotoluene by using a liquid-phase oxidation method under the action of a catalyst, controlling a reaction temperature to 75-85 DEG C, terminating the reaction when the content of the parabromotoluene in the reaction system accounts for 0.5wt% of an initial content, cooling, filtering so as to obtain a crude product and filtrate of 4-bromobenzoic acid, and further purifying the crude product of the 4-bromobenzoic acid at one step, thereby obtaining a finishedproduct. The melting point of the finished product of the 4-bromobenzoic acid is 252-254 DEG C. In addition, the 4-bromobenzoic acid prepared by using the method is high in yield, that is, the yieldis up to 98% or greater, meanwhile, the finished product is high in purity, that is, the purity is up to 99% or greater, the defects that a product prepared by using a conventional preparation methodis low in purity and low in yield can be overcome, and in addition, the method provided by the invention is simple and easy in raw material obtaining, low in cost and wide in application prospect.

The invention relates to a self-flame retardant antibacterial aqueous polyester resin and a preparation method thereof. The resin comprises the following components in parts by weight: 6.0-12.0 partsof organic anhydride, 3.0-5.0 parts of carboxylic acid Schiff base, 3.0-8.0 parts of polybasic acid, 6.0-20.0 parts of polyhydric alcohols, 1.2-3.5 parts of 2-chloro-5-bromobenzoic acid, 1.5-3.5 partsof dimethylolpropionic acid, 2.0-5.0 parts of xylene, 2.0-5.0 parts of a neutralizing agent and 45.0-65.0 parts of deionized water. The self-flame retardant antibacterial aqueous polyester resin provided by the invention is good in coloring property, low in viscosity, high in hardness, good in fullness, good in brightness, and the like, is free of external flame retardant or antibacterial agent when an aqueous coating is prepared, is long in flame retardant and antibacterial effect lasting and high in efficiency, and can be applied to inner and outer wall coatings, aqueous industrial coatings, aqueous wood product coatings, and the like.

The invention provides a preparation method of a key intermediate 1-(7-bromo-9,9-difluoro-9H-fluoren-2-yl)-2-chloroethanone. The method comprises the steps as follows: 2-amino-5-bromobenzoic acid is taken as a raw material, and subjected to diazotization, iodination,synthesis of 5-bromo-2-iodobenzoic acid, methylation, coupling reaction with phenylboronic acid, ester hydrolysis, acyl chlorination,intramolecular Friedel-Crafts alkylation, carbonyl reduction, iodization, fluorination and final reaction with 2-chloro-N-methoxy-N-methylacetamide to prepare the target product. The process adopts easily available starting raw materials, is low in price and free of hazardous process and has mild reaction conditions..

The invention relates to an artificial synthesis method of neomarchantin A, which comprises the following step: by using 4-hydroxy-3-methoxybenzaldehyde and methyl parabromobenzoate as initial raw materials, carrying out chemical reaction to finally obtain the neomarchantin A. The method provided by the invention utilizes the artificial synthesis process to obtain the neomarchantin A for the first time and can continuously and abundantly synthesis neomarchantin A, and the overall yield is 18.9%, thereby providing favorable technical supports for subsequent large-scale production of neomarchantin A.

The present invention provides a process for preparing pemetrexed disodium and its intermediate, 4-(4-carbomethoxyphenyl)butanal. The process for preparing the intermediate comprises the following steps: condensing methyl 4-bromobenzoate with 3-buten-1-ol; extracting with an organic solvent during the work-up; adding silica gel to decolorize; and evaporating the organic solvent to give 4-(4-carbomethoxyphenyl)butanal. The product obtained by the present process, with a yield of higher than 80%, and a purity measured by GC of higher than 95%, may be directly used in the next bromination reaction for synthesizing pemetrexed disodium without purification. The present process is suitable for industrial production, as the operation is simple and the reagents used are cheap and readily available.

The invention discloses a modified cotton straw adsorbent for removing pyrazinamide through adsorption. The modified cotton straw adsorbent is prepared through the following steps of selecting cotton straws of which the particle size is 4-6mm, washing the cotton straws with deionized water, absolute ethyl alcohol and an NaOH solution and drying to obtain a substance Q; modifying the substance Q with a mixed liquid prepared from urea sulfate, guanidine nitrate, rhodium nitrate, cobalt sodium nitrate and iridous chloride, thus obtaining a substance R; modifying the substance R with a mixed liquid prepared from ceric ammonium nitrate, pyridine sulfur trioxide, duroquinol, pyridine sulfur trioxide, duroquinol, 1,5-naphthalene disulfonic acid, 2-amino-3-bromobenzoic acid and N-ethyl acetamide, thus obtaining a substance S; and modifying the substance S with a mixed liquid prepared from cupric nitrate, cadmium nitrate, lithium chloride, magnesium chloride and stannous chloride, thus obtaining a substance, namely the modified cotton straw adsorbent for removing the pyrazinamide through adsorption.

According to the method, 2-methyl-5-bromobenzoic acid is adopted as a raw material, and Suzuki coupling reaction, condensation reaction, dehydration cyclization reaction and amide condensation reaction are performed to finally obtain the fluralan. According to the synthesis method, the reaction cost is reduced, the yield is improved, and the reaction period is shortened.

The invention discloses a coumarin-acridone fluorescent probe, and a preparation method and an application thereof. The chemical name of the coumarin-acridone fluorescent probe is 4-methyl-2H-pyrano[2,3a]acridin-2,12(7H)-dione acetate. The preparation method is characterized in that o-bromobenzoic acid and 1-amino-4-methylcoumarin which are taken as initial raw materials undergo a Cu-catalyzed Ullmann reaction and a ring closing reaction to synthesize the coumarin-acridone fluorescent probe. The fluorescent probe has specific selectivity to iron ions, basically has no change with other commonmetal ion fluorescence signals, and has high sensitivity and low detection limit. The coumarin-acridone fluorescent probe can be applied to in-vitro fluorescence detection of iron ions.

The invention discloses a synthesis method of 2-bromo-3-fluobenzoic acid. The method comprises the following steps of (1) using o-bromo fluorobenzene as starting raw materials; performing proton abstraction through lithium diisopropylamide; performing reaction with trimethylchlorosilane to generate 3-bromo-2-fluorophenyl trimethylsilane; (2) forming an intermediate of 4-trimethylsilyl-3-bromo-2-bromobenzene lithium saltsby 3-bromo-2-fluorophenyl trimethylsilane under the effect of lithium diisopropylamide; then, performing reaction with carbon dioxide to generate 4-trimethylsilyl-3-bromo-2-bromobenzoic acid; (3) performing reaction on 4-trimethylsilyl-3-bromo-2-bromobenzoic acid and fluorine-containing reagents for desilylation to obtain the 2-bromo-3-fluobenzoic acid. The intermediate obtained by the method does not have isomer; the separation is easy; the obtained product has high purity; a simple and compact path is provided for the synthesis of compounds.

The invention discloses a method for preparing alcohol compound through uncatalyzed reaction of aromatic carboxylic acid. The method includes: in an inert gas atmosphere, well stirring and mixing pinacolborane and carboxylic acid in a reaction bottle after dehydration deoxygenation, allowing reaction for 6-12h to obtain borate, and further hydrolyzing into alcohol, wherein the carboxylic acid is benzoic acid, 4-bromobenzoic acid, 4-fluorobenzoic acid, 1-naphthoic acid and 2-methoxybenzoic acid. The carboxylic acid is utilized to be in hydroboration reaction with borane efficiently in a catalyst-free condition for the first time, and a carbonyl compound is enabled to be in hydroboration reaction with borane to prepare borate which is further hydrolyzed into alcohol, in this way, a new scheme is provided.

The invention belongs to the technical field of TiO2 composite materials, and discloses a method for preparing a conjugated microporous polymer TiO2 composite nano antibacterial agent by an in-situ method. The method comprises the following steps: ultrasonically dispersing TiO2 particles: adding a certain amount of TiO2 into a beaker containing toluene, sealing the beaker by using a preservative film, and putting the sealed beaker into an ultrasonic cleaner for oscillation to obtain a mixture A; adding 4, 4 '-diethynyl biphenyl, 2, 4, 6-tribromobenzoic acid, CuI, Pd (PPh3) 2Cl2 and PPh3 into a three-necked bottle filled with triethylamine and methylbenzene; according to the method for preparing the conjugated microporous polymer TiO2 composite nano antibacterial agent, the TiO2 particles grow on the surface and inside of a conjugated microporous polymer in an in-situ polymerization mode, the conjugated microporous polymer has the characteristics of high stability, high hydrophobicity, high photon activity and the like, the band gap of TiO2 can be effectively widened, and the antibacterial property of the conjugated microporous polymer is improved. Therefore, the photocatalytic antibacterial activity of the composite material is improved, and bacterial inactivation is accelerated.

The invention aims to provide a method for synthesizing 4-bromo-2-(4 '-ethoxy-benzyl)-1-chlorobenzene, which has shorter steps and is greener, and provides a more effective synthesis strategy for production of key intermediates of SGLT-2 inhibitor drugs such as dapagliflozin, sotagliflozin, ertugliflozin and the like. The method comprises the following steps: selecting 2-chlorine-5-bromobenzoic acid and phenethyl ether, completing a direct acylation reaction in the presence of trifluoroacetic anhydride by taking boron trifluoride diethyl ether as a catalyst, adding triethylsilane without treatment, and carrying out a one-pot reaction to obtain the target compound 4-bromo-2-(4 '-ethoxy-benzyl)-1-chlorobenzene.