- Br?nsted acid-catalyzed chlorination of aromatic carboxylic acids
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The chlorination of aromatic carboxylic acids with SOCl2 has been effectively performed by reacting with a Br?nsted acid as the catalyst. Based on this discovery, an efficient catalytic method that is cheaper than traditional catalytic methods was developed. 20 substrates were chlorinated offering excellent yields in a short reaction time. And the SOCl2/Br?nsted acid system has been used in a larger scale preparative reaction. A dual activation mechanism was proposed to prove the irreplaceable system of SOCl2/Br?nsted acid.
- Yu, Zhiqun,Yao, Hongmiao,Xu, Qilin,Liu, Jiming,Le, Xingmao,Ren, Minna
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supporting information
p. 685 - 689
(2021/04/09)
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- Environment-friendly production process of 2, 4-dichloro-5-fluorobenzoyl chloride
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The present invention relates to the field of chemistry, and particularly provides a preparation method of 2, 4-dichloro-5-fluorobenzoyl chloride. According to the invention, dimerization by-productsof the 2, 4-dichloro-5-fluorobenzoyl chloride produced by a carbon tetrachloride method are subjected to alkaline hydrolysis under the action of a catalyst, then after acidification, the processed product reacts with trichloride generated by condensation of a main reaction to be converted into 2, 4-dichloro-5-fluorobenzoyl chloride, and the yield reaches over 99.8%.
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- Quinolone derivatives and preparation method and application thereof
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The invention relates to quinolone derivatives and a preparation method and application thereof. According to the invention, the structure of quinolone is modified, a substituent group on a nitrogenatom at the position 1 is derived, a diphenyl ether structural unit with biological activity is introduced, and meanwhile, the position 3, the position 6 and the position 7 of a main ring are properlychanged to form the novel quinolone derivatives. A quinolone compound structure is innovated, a bioactive molecule splicing method is adopted, and the diphenyl ether structural unit is introduced into quinolone molecules through C-N bonds to prepare a series of the novel quinolone derivatives are prepared, so the range of the structure is expanded; in addition, the quinolone derivatives preparedby the invention have antibacterial activity and antitumor activity, and are expected to be expanded in application range; an efficient acid-binding agent and an efficient catalyst are introduced, anda one-pot technology is adopted, so preparation of the series of derivatives is successfully achieved, separation and purification of intermediate products are avoided, reaction procedures are reduced, reaction time is greatly shortened, and the production efficiency is improved.
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Paragraph 0054-0056
(2020/05/01)
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- Preparation method for fluoroquinolones intermediate 2,4-dichloro-5-fluorobenzoyl chloride
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The invention discloses a preparation method for fluoroquinolones intermediate 2,4-dichloro-5-fluorobenzoyl chloride, and belongs to the technical field of the pharmaceutical synthesis. Through changing a compound IV into a compound V* and raw material 2,4-dichlor fluorbenzene, easy explosive materials of hydrogen peroxide and the like are avoided from being used. The compound V*, through a one-step reaction, is changed into the compound 2,4-dichloro-5-fluorobenzoyl chloride. A synthesized product is higher in purity, a total yield of a two-step reaction is higher, the generated starting raw material 2,4-dichlor fluorbenzene can be recycled, and carboxylate (V*) is changed into acyl chloride (II), and hydrochloric acid is not generated, pollution can be reduced. The method is more superiorto an existing technology, capable of increasing a resource utilization rate, reducing a production risk, reducing production cost, and more suitable for industrial production.
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Paragraph 0054; 0056; 0057; 0059; 0060; 0062
(2019/05/20)
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- Synthesis method of 2,4-dichloro-5-fluorobenzoyl chloride
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The invention relates to a synthesis method of a quinolone drug intermediate 2,4-dichloro-5-fluorobenzoyl chloride. The synthesis method comprises: preparing 2,4-dichloro-5-fluorobenzoyl chloride from2,4-dichlorofluorobenzene, carbon dioxide and carbon tetrachloride under the action of a cationic resin catalyst. According to the present invention, with the synthesis method, the problems of too long process route, complex post-treatment, high requirement on equipment, use of highly toxic chemicals, low yield, poor product quality and the like unsuitable for industrial production are solved; and the synthesis method of the present invention has advantages of inexpensive and easily-available raw materials, short process route, good production safety, easy separation of the catalyst, less emission of waste acid, simple post-treatment, high yield and good product quality, and is suitable for industrial continuous production.
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Paragraph 0065; 0066; 0067; 0068; 0069; 0070; 0071-0083
(2019/04/18)
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- A benzoyl - O - (4 - trifluoromethyl) salicylic amide compound and use thereof
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The invention discloses an O-benzoyl-(4-trifluoromethyl) salicylamide compound represented by formula (I), and applications of the O-benzoyl-(4-trifluoromethyl) salicylamide compound in preparing antitumor drugs, and especially in preparing drugs used for treating cervical cancer, human placental trophoblast cancer, leukemia, cervical squamous cell carcinoma, endometrial cancer, and breast cancer.
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Paragraph 0047-0050
(2018/01/20)
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- Preparation method of 2,4-dichloro-5-fluorobenzoyl chloride
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The invention discloses a preparation method of 2,4-dichloro-5-fluorobenzoyl chloride and belongs to the field of organic synthesis. The preparation method comprises the following steps: with 2,4-dichlorofluorbenzene as a raw material, performing friedel-crafts reaction and hydrolyzation to generate an intermediate, 2,4-dichloro-5-fluorobenzoyl chloride; and hydrolyzing, oxidizing and acylating a byproduct, biopolymer (III), generated by the reaction to obtain a final compound (II), wherein the total yield is 88% or above. According to the invention, the raw material conversation ratio is 80% or above, the defects that existing raw materials are hardly available, and the utilization ratio is low are overcome, resources are saved, the production cost is lowered, and the preparation method is simple to operate and easy for amplified production.
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- Tubular continuous production method of 2, 4-dichloro-5-fluorobenzoyl chloride
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The invention provides a tubular continuous production method of 2, 4-dichloro-5-fluorobenzoyl chloride. The method includes: taking 2, 4-dichloro-5-fluoroacetophenone as the starting raw material, performing oxidation on the raw material with oxygen under the catalysis of a mixed acid system of nitric acid and sulfuric acid into 2, 4-dichloro-5-fluorobenzoic acid, then carrying out acylation by bis(trichloromethyl)carbonate (BTC) so as to obtain the final product 2, 4-dichloro-5-fluorobenzoyl chloride. The method provided by the invention adopts a continuous tubular reactor, involves few online reaction materials, and is conducive to DCS control, as a catalyst, nitric acid has a small dosage and can be recycled, oxygen participates in the reaction as an oxidizing agent, and bis(trichloromethyl)carbonate (BTC) substitutes thionyl chloride to serve as an acylation reagent, thus saving cost, and avoiding emission of nitrogen oxides, sulfur dioxide and other harmful gas.
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Paragraph 0024-0026
(2017/08/31)
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- A 2,4-dichloro-5-fluoro-benzoyl chloride method for the preparation of
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The invention relates to a method for synthesizing 2,4-dichloro-5-fluorobenzoyl chloride suitable for industrialized production. According to the method, the yield of the product can be further increased, a process route can be simplified, and the method is suitable for industrialized production.
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Paragraph 0111; 0112
(2017/03/08)
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- A 2,4-dichloro-5-fluoro-benzoyl chloride method for the synthesis of
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The invention discloses a method for synthesizing 2,4-dichloro-5-fluorobenzoyl. The method comprises the following steps: reacting 2,4-dichlor fluorbenzene and CCl4 serving as initial raw materials under actions of solid acid catalyst S2O82-/Sm2O3-ZrO2-Al2O3 and AlCl3 to generate 2,4-dichloro-5-fluoro-(trichloromethyl) benzene, and catalyzing and hydrolyzing by FeCl3. The method has the advantages that: the solid acid catalyst S2O82-/Sm2O3-ZrO2-Al2O3 can be conveniently recycled, the yield is high, so that the proportion of biopolymer byproducts can be reduced; use of high-pollution high-risk raw materials can be avoided, the operation safety is high, and pollutant emission is little; and the method can be used for breaking through the technical bottleneck of the reaction of aryl halide and CCl4, and massively consuming CCl4 which destroys the ozone layer by introducing acyl chloride functional group on an aromatic ring by adopting the CCl4 as a raw material.
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Paragraph 0037-0038
(2017/02/24)
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- Synthesis and bioactivity of 6-phenyl-4,5-dihydro-3(2H)-pyridazinone derivatives
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A series of 6-phenyl-4,5-dihydro-3(2H)-pyridazinone derivatives was prepared and examined for cardiotonic activity. The structures of these new pyridazinone derivatives were confirmed by IR, 1H-NMR and mass spectrum. The cardiotonic activities of these compounds were studied on isolated perfused toad heart and compared with the activity of levosimendan (CAS 141505-33-1). Compound 5a emerged as the most interesting compound in this series with potential cardiotonic activity. ECV Editio Cantor Verlag.
- Wang, Teng,Dong, Ying,Wang, Li-Chen,Chen, Zhen
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p. 641 - 646
(2008/03/11)
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- Syntheses and insecticidal activities of novel 2,5-disubstituted 1,3,4-oxadiazoles
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Nine novel symmetrical and asymmetrical 2,5-disubstituted 1,3,4-oxadiazoles have been synthesized by a facile and mild method with high yield. Meantime, it was found that the fluorine was easy substituted by hydrazine in polyhalogen-substituted aroyl hydrazine. The preliminary bioassay tests show that two of the compounds (D5> and D6) exhibited a significant insecticidal activity (LC50=116.02 and 70.93 mg l-1) on armyworm, Leucania separata Walker. Using the Drug Discovery Workbench (DDW) (Cerius2), structure-activities relationship was studied.
- Zheng, Xiumian,Li, Zhong,Wang, Yanli,Chen, Weidong,Huang, Qingchun,Liu, Chuanxiang,Song, Gonghua
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p. 163 - 169
(2007/10/03)
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- Syntheses and insecticidal activities of novel 2-fluorophenyl-5-aryl/cyclopropyl-1,3,4-oxadiazoles
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Two 2-fluorophenyl-5-substitued cyclopropyl-1,3,4-oxadiazoles (IIIa-b) with cis/trans isomers were synthesized from the corresponding hydrazide (Ia) and aroyl chlorides by two-step reactions. Six asymmetrical 2-(2,4-dichloro-5-fluorophenyl)-5-aryl-1,3,4-oxadiazoles (IIIc-h) were obtained by one step reaction of 2,4-dichloro-5-fluorobenzoic acid hydrazide (Ic) with the corresponding aromatic carboxylic acid in the presence of phosphorus oxychloride under reflux. However, the similar reaction of 4-fluorophenoxyacetic acid hydrazide (Ib) with 2,4-dichloro-5-fluorobenzoic acid failed to yield the desired asymmetrical 2-(2,4-dichloro-5-fluorophenyl)-5-(fluorophenoxymethyl)-1,3,4-oxadiazole, and the resulting product was characterized as symmetrical 2,5-bis(2,4-dichloro-5-fluorophenyl)-1,3,4-oxadiazole (DCFPO). A possible reaction mechanism is suggested. Insecticidal activities of these nine new compounds against armyworms (Pseudaletia separata Walker) were determined.
- Shi, Wei,Qian, Xuhong,Song, Gonghua,Zhang, Rong,Li, Rongpo
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p. 173 - 179
(2007/10/03)
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