- Production process of flumioxazin herbicide
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The invention discloses a production process of a flumioxazin herbicide. The process is characterized by comprising the following steps: S1, synthesizing 2-nitro-5-fluorophenol; S2, synthesizing ethyl 2-(5-fluoro-2-nitrophenoxy) acetate; S3, synthesizing 7-fluoro-2H-1, 4-benzoxazine-3 (4H)-ketone; S4, synthesizing 7-fluoro-6-nitro-2H-1, 4-benzoxazine-3 (4H)-ketone; S5, synthesizing 7-fluoro-6-amino-2H-1, 4-benzoxazine-3 (4H)-ketone; S6, synthesizing 7-fluoro-6-(3, 4, 5, 6-tetrahydro)phthalimido-1, 4-benzoxazine-3 (4H) ketone; and S7, synthesizing the flumioxazin. The method has the advantages of low raw material price, few byproducts and light pollution.
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Paragraph 0013-0015
(2021/07/01)
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- Method for preparing 5-fluoro-2-nitrophenol
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The invention belongs to the technical field of organic synthesis and particularly relates to a method for preparing 5-fluoro-2-nitrophenol. The method is used for solving the technical problem that the existing methods for preparing the 5-fluoro-2-nitrophenol are long in reaction time and are adverse to industrialized operation. In order to solve the technical problem, the technical scheme adopted is as follows: the method for preparing the 5-fluoro-2-nitrophenol, provided by the invention, comprises the following step: subjecting 2,4-difluoronitrobenzene to a reaction under the condition ofcoexisting of alkali, water and an organic solvent, thereby obtaining the 5-fluoro-2-nitrophenol. According to the method, through adding the organic solvent into a reaction system, the reaction ratecan be accelerated, the reaction time is effectively shortened, the energy consumption is lowered, and thus, industrialized application is better facilitated.
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Paragraph 0031-0059
(2020/01/12)
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- 5-fluoro-2-nitrophenol preparation method
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The invention belongs to the field of organic synthesis, and particularly relates to a 5-fluoro-2-nitrophenol preparation method. In the prior art, the existing synthesis method has disadvantages of low conversion rate and long reaction time so as not to easily achieve industrial operation. A purpose of the present invention is to solve the technical problem in the prior art. The technical schemeis to provide a 5-fluoro-2-nitrophenol preparation method, which comprises: a) carrying out a reaction on 2,4-difluoronitrobenzene and NH 3 to obtain 5-fluoro-2-nitroaniline; and b) carrying out a reaction on the 5-fluoro-2-nitroaniline under the actions of sulfuric acid and sodium nitrite to obtain the 5-fluoro-2-nitrophenol. According to the present invention, the 5-fluoro-2-nitrophenol preparation method has advantages of good selectivity, almost no side reaction, high yield, short reaction time, simple operation and easy industrialization.
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Paragraph 0023; 0042-0045
(2018/06/15)
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- Method for synthetizing 2-(5-fluorine-2-nitryl-phenoxyl) methyl acetate
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The invention discloses a method for synthetizing 2-(5-fluorine-2-nitryl-phenoxyl) methyl acetate. According to the method, 2,4-difluoronitrobenzene is used as raw materials; the 2-(5-fluorine-2-nitryl-phenoxyl) methyl acetate (a flumioxazin intermediate) is obtained through hydroxy substitution and etherification reaction. The synthesis method provided by the invention has the advantages that the 2,4-difluoronitrobenzene is used as raw materials; the price is low; the obtaining is easy, so that the production cost is reduced to a certain degree; the intermediate 1 directly reacts with methyl chloroacetate; the operation is simple; the raw materials can be repeatedly used, so that the production cost is reduced; through etherification reaction, byproducts of hydrochloric acid are recovered; no byproducts of sylvite are generated; environment-friendly and green effects are achieved; the aftertreatment operation is simple and convenient; in addition, the raw materials are cheap and can be easily obtained; the reaction condition are mild; the operation is simple and convenient; the popularization to scale production is favorably realized.
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Paragraph 0024-0025; 0030-0033
(2018/04/01)
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- Preparation method of Anacetrapib key intermediate
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The invention relates to a preparation method of an Anacetrapib key intermediate 1-bromo-4-fluoro-5-isopropyl-2-methoxybenzene. The preparation method comprises the following steps: hydrolyzing an initial raw material 2,4-difluoronitrobenzene to obtain 4-fluoro-2-hydroxynitrobenzene, methylating 4-fluoro-2-hydroxynitrobenzene to obtain 4-fluoro-2-methoxynitrobenzene, carrying out nitro group reduction to form 4-fluoro-2-methoxyaniline, carrying out diazo bromination to obtain 4-fluoro-2-methoxybromobenzene, carrying out Friedel-Crafts acylation to obtain 2-fluoro-4-methoxy-5-bromoacetophenone, carrying out a condensation reaction to obtain 2-(2-fluoro-4-methoxy-5-bromophenyl)-propane-2-ol, carrying out an elimination reaction to obtain 1-bromo-4-fluoro-2-methoxy-5-(1-methylvinyl)benzene, and hydrogenating the 1-bromo-4-fluoro-2-methoxy-5-(1-methylvinyl)benzene to obtain 1-bromo-4-fluoro-5-isopropyl-2-methoxybenzene. The preparation method has the advantages of realization of low cost, good quality and high yield of the above final product, mild reaction conditions, simplicity in operation, and easiness in industrialization.
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Paragraph 0033; 0034
(2017/04/25)
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- Spiro aryl phosphorus oxide or sulfide
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The invention discloses a spiro aryl phosphorus oxide or sulfide as ALK inhibitor, and in particular discloses a compound shown in a formula (I) as an ALK inhibitor or a pharmaceutically acceptable salt thereof.
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Paragraph 0367; 0368; 0369; 0370
(2016/10/08)
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- ONE POT PROCESS FOR THE CONVERSION OF AROYL CHLORIDES TO ACYL THIOUREAS
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The present invention disclose an improved one pot process for synthesis of acyl thioureas of formula (I), with yield greater than 80%, from aroyl chlorides of formula (I) wherein, R' is an aryl or a heteroarylene group substituted with one or more groups selected from hydrogen, alkyl, alkylene, alkynyl, alkoxy, alkenyloxy, halo, hydroxyl, nitro, amino, carboxyl, ester, halogenated hydrocarbon or an aryl or heteroaryl; R" and R"' are selected independently from hydrogen, alkyl, alkylene, alkynyl, alkoxy, alkenyloxy, halo, hydroxyl, nitro, amino or halogenated hydrocarbon.
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Page/Page column 8; 13
(2014/06/24)
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- Non-steroidal dissociated glucocorticoid agonists: Indoles as A-ring mimetics and function-regulating pharmacophores
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We report a SAR of non-steroidal glucocorticoid mimetics that utilize indoles as A-ring mimetics. Detailed SAR is discussed with a focus on improving PR and MR selectivity, GR agonism, and in vitro dissociation profile. SAR analysis led to compound (R)-33 which showed high PR and MR selectivity, potent agonist activity, and reduced transactivation activity in the MMTV and aromatase assays. The compound is equipotent to prednisolone in the LPS-TNF model of inflammation. In mouse CIA, at 30 mg/kg compound (R)-33 inhibited disease progression with an efficacy similar to the 3 mg/kg dose of prednisolone.
- Betageri, Raj,Gilmore, Thomas,Kuzmich, Daniel,Kirrane, Thomas M.,Bentzien, J?rg,Wiedenmayer, Dieter,Bekkali, Younes,Regan, John,Berry, Angela,Latli, Bachir,Kukulka, Alison J.,Fadra, Tazmeen N.,Nelson, Richard M.,Goldrick, Susan,Zuvela-Jelaska, Ljiljana,Souza, Don,Pelletier, Josephine,Dinallo, Roger,Panzenbeck, Mark,Torcellini, Carol,Lee, Heewon,Pack, Edward,Harcken, Christian,Nabozny, Gerald,Thomson, David S.
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scheme or table
p. 6842 - 6851
(2011/12/22)
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- USE OF INTERMEDIATES ((R ) -2,2, 4-TRIMETHYL-L, 3-DIOXOLANE-4-YL) METHANOL (A), 3-F LUORO-4-NITRO-PHENOL (B) AND 1- (4-CHLORO- BENZYL) -PIPERIDIN-4-YLAMINE (C)
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The present invention relates to novel processes for the preparation of intermediate compounds which can be used to prepare therapeutic agents. The present invention also relates to novel intermediate compounds which can be used to prepare therapeutic agents. More specifically, the invention relates to the use of intermediates ((R) -2,2,4-trimethyl-l, 3- dioxolane-4 -yl) methanol (A), 3-f luoro-4-nitro-phenol (B) and 1- (4-chloro-benZyl) -piperidin-4-ylamine (C).
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Page/Page column 8; 19-20
(2009/04/25)
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- Mild cleavage of aryl mesylates: Methanesulfonate as potent protecting group for phenols
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A mild protocol for the chemoselective deprotection of aryl methanesulfonates is described. The transformation can be conducted on highly functionalized substrates and renders the methanesulfonate a useful, previously underutilized protecting group for phenols.
- Ritter, Tobias,Stanek, Kyrill,Larrosa, Igor,Carreira, Erick M.
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p. 1513 - 1514
(2007/10/03)
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- Leaving group effect in the cleavage of picolinate esters catalyzed by hydroxy-functionalized metallomicelles
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Micellar aggregates of complexes of transition metal ions with the hydroxy-functionalized surfactant 1a are very effective catalysts of the cleavage of activated esters of α-amino acids. To ascertain their effectiveness toward unactivated esters, a systematic kinetic study was undertaken employing as substrates the picolinic acid esters 3a-1, the pK(a) of their alcoholic portion spanning more than 12 units from 3.6 to 16. The leaving group effect was investigated in water, pH = 6.3, in the absence and presence of Cu2+ ions, in the presence of the nonmicellar complex 2·Cu2+, and in the presence of micellar aggregates made of 1a·Cu2+ or of its O-methylated analog 1b·Cu2+. In the presence of free metal ions the leaving group effect is negligible in the case of esters with good leaving groups (pK(a) 2+ complexes, either micellar 1a or nonmicellar 2, the leaving group effect is relatively small in the case of activated substrates (pK(a) 2+ ions at pH = 7.5. The largest rate enhancements were observed in the case of the most activated substrates in micellar solutions of the 1a·Cu2+ complex (1.6 x 106 folds for 3b over the rate in pure buffer), considerably larger than those in the presence of its nonmicellar analog (4.2 x 104 folds) or of the free metal ion (1.5 x 103 folds). However, in the case of unactivated esters, such kinetic benefits vanish out and the metal ion alone is even more effective (2 x 104 folds acceleration for 31 in presence of Cu2+) than its complexes, either in the monomeric (7.3 x 103 folds) or in the micellar form (4.6 x 103 folds). On the basis of the possible changes in the mechanistic pathway depending on the nature of the leaving group, a rationale is offered.
- Scrimin,Tecilla,Tonellato
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- Process for the preparation of 2-nitro-5-fluoro- or -5-chlorophenol
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The present invention relates to a process for the preparation of isomerically pure 2-nitro-5-fluoro- or -5-chlorophenol, by reacting 2,4-difluoronitrobenzene or 2,4-dichloronitrobenzene with aqueous alkali metal or alkaline earth metal hydroxide solution or suspension in the absence of organic solvents or other solubility promoting substances at temperatures from about 20° C. to about 190° C., adjusting the pH of the reaction mixture to about 1 to about 6 by the addition of acid, steam distilling the resultant product and isolating it from the distillate after cooling.
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