- Synthesis method of fluorine-containing phenol structure compound
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The invention discloses a synthesis method of a fluorine-containing phenol structure compound, and belongs to the technical field of chemical synthesis. Fluorine-containing benzoic acid is subjected to a one-pot reaction in a solvent under the action of alkali to obtain fluorine-containing phenate, and fluorine-containing phenol is obtained after acid regulation and dissociation. The synthesis method has the advantages of rich, cheap and easily available raw material structure, short synthesis steps, mild reaction conditions, simple and convenient operation, high synthesis yield, good productquality, wide application range and the like, and is suitable for simple and efficient synthesis of various high-value and high-purity fluorine-containing phenol compounds.
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Paragraph 0023-0024
(2021/03/13)
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- A aqueous phase preparation 2, 6 - [...] method
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The invention relates to a green preparation 2, 6 - [...] synthetic method, to industrial product is 2, 6 - difluoro-benzamide as the starting material, passes through the aqueous phase Huffman degradation reaction, the aqueous phase diazotisations directly after the hydrolysis, direct concentrated nitric acid nitration, the iron powder reduces the aqueous phase, the aqueous phase with the aqueous phase to diazotization coupling reaction of phenol, after five step process for preparing aqueous phase reactions 2, 6 - [...] production process and corresponding various process conditions. The beneficial effect of the present invention is: select industrialized product 2, 6 - difluoro-benzamide as the raw material, raw materials are easy, low cost, through the aqueous phase reaction and solvent-free reaction for the preparation of 2, 6 - [...], its mild reaction conditions and environmental, safety and high efficiency. The present invention provides a kind of environmental protection, model, high efficiency can be used for the industrial production of 2, 6 - [...] green synthetic pathway.
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- Method for preparing 2,6-difluoroindophenol acetate
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The invention relates to a novel synthetic method for preparing 2,6-difluoroindophenol acetate, in particular to a production process for preparing the 2,6-difluoroindophenol acetate successively by virtue of six reaction steps of industrialized product 2,6-difluorobenzamide serving as a raw material, i.e. Hofmann degradation reaction, diazotization and direct hydrolysis, nitrification with concentrated nitric acid, catalytic hydrogenation reduction with palladium on carbon, diazotization and phenol coupling reaction and esterification under the condition of acetic anhydride and various corresponding process conditions. The method has the beneficial effects that the industrialized product 2,6-difluorobenzamide is used as the raw material, the raw material is easy to obtain, the price is low, and the reaction condition is mild and environmentally friendly. The invention provides a novel efficient way for producing the 2,6-difluoroindophenol acetate in an industrialization manner.
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- A practical method for preparation of phenols from arylboronic acids catalyzed by iodopovidone in aqueous medium
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A novel and efficient strategy for the ipso-hydroxylation of arylboronic acids to phenols has been developed using inexpensive, readily available, air-stable water-soluble povidone iodine as catalyst and aqueous hydrogen peroxide as oxidizing agent. The reactions were performed at room temperature under metal-, ligand- and base-free condition in a short reaction time. The corresponding substituted phenols were obtained in moderate to good yields by oxidative hydroxylation of arylboronic acids in aqueous medium.
- Dong, Bin,Ke, Yanxiong,Lu, Guangying,Ren, Jiangmeng,Ren, Yaoyao,Zeng, Bu-Bing,Zhou, Bin
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- Process for preparing phenol fluoride by amine catalytic method
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The invention relates to a process for preparing phenol fluoride by amine catalytic method and belongs to the technical field of chemical synthesis.The process comprises: adding phenol and a catalyst sequentially into a reactor for heating, introducing fluorine-nitrogen mixed gas into the reactor for reacting, purging with nitrogen after reacting to obtain crude phenol fluoride, charging purging gas and reaction tail gas sequentially into an activated carbon absorber and a solid sodium lime absorber for adsorption, discharging finally obtained non-condensable gas at a great height, rectifying and separating the crude phenol fluoride to obtain o-fluorophenol, p-fluorophenol, 2,4-difluorophenol and 2,6-difluorophenol.The problem that an existing preparation process has low product yield, high solvent consumption, high cost and environmental pollution is solved herein, the process has the advantages of material conversion completeness, little byproduct and low production cost, no additional solvent is added to maintain a certain temperature range, cost is saved, and solvent loss is reduced.
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Paragraph 0028; 0030; 0038; 0054-0058
(2017/04/03)
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- 1-cyclopropyl-4-oxo-7-fluoro-8-methoxy -1,4-dihydro-quinoline-3-carboxylic acid synthesizing method
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The invention discloses a synthesis method of 1-cyclopropyl-4-oxo-7-fluoro-8-methoxy-1,4-dihydroquinolyl-3-carboxylic acid. The synthesis method comprises the following reaction steps: reacting m-difluorophenyl with an organolithium reagent, reacting an obtained aryllithium intermediate with borate, quenching to obtain 2,6-difluorophenylboronic acid and 2,6-difluorophenylborate, reacting 2,6-difluorophenol obtained through oxidation with a methylating reagent, reacting the obtained 2,6-difluorophenylmethyl ether with the organolithium reagent, reacting the obtained corresponding aryllithium intermediate with carbon dioxide, reacting the obtained product with an acylchlorinating reagent to obtain 2,4-difluoro-3-methoxy benzoyl chloride, and performing cyclization, hydrolysis and the like to obtain the 1-cyclopropyl-4-oxo-7-fluoro-8-methoxy-1,4-dihydroquinolyl-3-carboxylic acid. The synthesis method has the advantages as follows: raw materials are easy to obtain; the yield in each step is high; the atom economy is high; the synthesis method is suitable for industrial application.
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Paragraph 0023; 0090; 0091
(2017/01/26)
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- Quinolinone compound and application thereof in drugs
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The invention relates to a quinolinone compound and application thereof in drugs, particularly relates to a novel quinolinone compound, a pharmaceutical composition thereof and use of the compound or the pharmaceutical composition in preparing drugs. The drug is used for protecting, disposing, treating or alleviating HIF-related and/or EPO-related diseases of patients, wherein the HIF-related and/or EPO-related diseases comprise anemia, vascular diseases, regional myocardial ischaemia, metabolic disturbance, wound healing and the like.
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Paragraph 0479; 0480; 0481; 0482
(2016/10/07)
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- Trichlorophenyl formate: Highly reactive and easily accessible crystalline CO surrogate for palladium-catalyzed carbonylation of aryl/alkenyl halides and triflates
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The high utility of 2,4,6-trichlorophenyl formate, a highly reactive and easily accessible crystalline CO surrogate, is demonstrated. The decarbonylation with NEt3 to generate CO proceeded rapidly at rt, thereby allowing external-CO-free Pd-catalyzed carbonylation of aryl/alkenyl halides and triflates. The high reactivity of the CO surrogate enabled carbonylation at rt and significantly reduced the quantities of formate to near-stoichiometric levels. The obtained trichlorophenyl esters can be readily converted to a variety of carboxylic acid derivatives in high yields.
- Ueda, Tsuyoshi,Konishi, Hideyuki,Manabe, Kei
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p. 5370 - 5373,4
(2012/12/12)
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- Arylsilane oxidation - New routes to hydroxylated aromatics
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An efficient route to hydroxylated aromatics has been developed, via the oxidation of aryl organosilanes under functional group-tolerant and relatively mild conditions, using sub-stoichiometric amounts of fluoride promoters.
- Bracegirdle, Sonia,Anderson, Edward A.
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supporting information; experimental part
p. 3454 - 3456
(2010/07/16)
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- Enzymatic Baeyer-Villiger oxidation of benzaldehydes
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The selectivity of the chemical Baeyer-Villiger oxidation of benzaldehydes depends on steric and electronic factors, the type of oxidizing agent and the reaction conditions. Here we report on the enzymatic Baeyer-Villiger oxidation of fluorobenzaldehydes
- Moonen, Marielle J. H.,Westphal, Adrie H.,Rietjens, Ivonne M. C. M.,Van Berkel, Willem J. H.
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p. 1027 - 1034
(2007/10/03)
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- A mechanistic study of the alkaline hydrolysis of diaryl sulfate diesters
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Nearly all of the reported studies of reactions of sulfate diesters are for dialkyl or alkyl aryl diesters, which undergo reaction by carbon-oxygen bond fission. Sulfuryl transfer reactions of sulfate diesters (RO-SO 2-OR′) proceeding by attack at sulfur have been little explored. When both ester groups are aryl groups the hydrolysis reaction (sulfuryl transfer to water) occurs by way of attack at sulfur. The alkaline hydrolysis of diaryl sulfate diesters was shown to obey first-order kinetics with respect to [-OH] and proceed through S-O bond fission, in a mechanism that is most likely concerted. Activation parameters for 4-chloro-3-nitrophenyl phenyl sulfate and 4-nitrophenyl phenyl sulfate gave the following respective values: ΔH? = 88.0 ± 0.1 and 84.83 ± 0.06 kJ mol-1 and ΔS? = -37 ± 1 and -50.2 ± 0.5 J mol-1 deg-1. The dependence of the second-order rate constant for hydrolysis on leaving group pKa was analyzed giving a β1g slope of -0.7 ± 0.2 and a Leffler α parameter value of 0.36. A 15k kinetic isotope effect (KIE) for the hydroxide attack on 4-nitrophenyl phenyl sulfate of 1.0000 ±0.0005 and an 18k1g KIE value of 1.003±0.002 were obtained.
- Younker, Jarod M.,Hengge, Alvan C.
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p. 9043 - 9048
(2007/10/03)
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- Synthesis and mesomorphic properties of some fluorinated benzoate liquid crystals
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Three series of [4-(4′-n-alkyloxyphenyl)acetylenyl]-2,6- difluorophenyl fluorinated benezoates and one series of fluorinated benzoates with 2,3,5,6-tetrafluorophenylene group and semi-perfluorocarbon chain have been synthesized. Their phase transition temperatures have been measured by texture observation in a polarizing microscope and confirmed by DSC. For the series without fluorocarbon chains, increasing the quantity of fluorosubstituents on the terminal phenyl groups decreased nematic stability (TN-I), but the breadth of the SmA phase range was increased. Lateral fluorosubstitution in the central group lowered the nematic stability (TN-I) and decreased the breadth of the SmA phase range. The series with semiperfluorocarbon chains were more likely to form SmA phases than the series with hydrogencarbon chains, and with the increasing of fluorosubstituents quantity on the terminal phenyl groups nematic and SmA stability (TN-I and TsmA-N) were both decreased.
- Yang, Yong Gang,Chen,Tang,Wen
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- Synthesis intermediates containing a hexane ring and processes for their preparation
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The present invention relates to new fluorinated hexane compounds corresponding to the following general formula (II): STR1 in which X'2, X'3 and X'4 are the same or different, and denote a halogen or a pseudohalogen, preferably a halogen, more preferably chlorine and fluorine, with the condition that, when R1 is hydroxyl, cyano, amido, imido, ethoxy, benzyloxy, cyclohexyloxy and tert-butoxy, not all the halogens can simultaneously be chlorine and R4, R3 and R5 are simultaneously equal to H; R1 denotes a hydrogen, a hydrocarbon chain such as an alkyl chain, alkoxy, cycloalkyl ether, an aromatic group, aromatic ether or an alkoxy, carbonyl, carboxyl or acyloxy, cyano, amido, imido or hydroxyl group; R4 denotes a hydrogen, a fluorine atom, a hydrocarbon chain such as, for example, an alkyl chain, an aromatic group or a carbonyl, carboxyl or carboxamide group or else a radical joined to the hexane ring by a chalcogen or by an element of Group V, preferably of the first Period, such as an amido, alkoxy or acyloxy group; in which the radicals R3 and R5, which are different or preferably the same, denote a fluorine, or preferably hydrogen, atom or also a hydrocarbon chain as defined above in the case of R4.
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