- Preparation method of 4, 4, 4-trifluorobutyric acid
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The invention relates to a synthesis method of fluorine-containing alkyl acid, in particular to a preparation method of 4, 4, 4-trifluorobutyric acid, and belongs to the technical field of organic fluorine chemical industry. The preparation method of the 4, 4, 4-trifluorobutyric acid comprises the following steps: reacting a Grignard reagent CF3CH2CH2MgCl with carbon dioxide, and hydrolyzing under an acidic condition to obtain the 4, 4, 4-trifluorobutyric acid. According to the invention, by using a Grignard reaction method, a reaction can be carried out at normal pressure or low pressure and general temperature, the reaction condition is mild, the reaction time is short, and a byproduct is easy to separate; and according to the preparation method of the 4, 4, 4-trifluorobutyric acid, the reaction process is simple and easy to operate, the conversion rate is higher than 83% or above, byproducts are few, the solvent can be recycled, safety and environment friendliness are achieved, continuous feeding can be achieved, and large-scale industrial co-production is easy to achieve.
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Paragraph 0018-0044
(2022/03/18)
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- Direct C(sp3)?H Trifluoromethylation of Unactivated Alkanes Enabled by Multifunctional Trifluoromethyl Copper Complexes
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A mild and operationally simple C(sp3)?H trifluoromethylation method was developed for unactivated alkanes by utilizing a bench-stable CuIII complex, bpyCu(CF3)3, as the initiator of the visible-light photoinduced reaction, the source of a trifluoromethyl radical as a hydrogen atom transfer reagent, and the source of a trifluoromethyl anion for functionalization. The reaction was initiated by the generation of reactive electrophilic carbon-centered CF3 radical through photoinduced homolytic cleavage of bpyCu(CF3)3, followed by hydrogen abstraction from an unactivated C(sp3)?H bond. Comprehensive mechanistic investigations based on a combination of experimental and computational methods suggested that C?CF3 bond formation was enabled by radical–polar crossover and ionic coupling between the resulting carbocation intermediate and the anionic CF3 source. The methylene-selective reaction can be applied to the direct, late-stage trifluoromethylation of natural products and bioactive molecules.
- Choi, Geunho,Lee, Geun Seok,Park, Beomsoon,Kim, Dongwook,Hong, Soon Hyeok
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supporting information
p. 5467 - 5474
(2021/01/20)
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- ACETIC ACID (2,2,2-TRIFLUOROETHYL) AND MANUFACTURING METHOD THEREFOR
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PROBLEM TO BE SOLVED: To provide acetic acid (2,2,2-trifluoroethyl) useful as an electronic material and having higher purity compared to prior art, and a manufacturing method therefor. SOLUTION: There are provided acetic acid (2,2,2-trifluoroethyl) having content of 2,2,2-trifluoroethanol of 0.01 area% or less in analysis by a gas chromatograph equipped with a hydrogen flame ionization detector, content of 2-halo-1,1,1-trifluoroethane represented by the following formula (1) CF3CH2X (1), wherein X represents a chlorine atom or a bromine atom, of 0.01 area% or less, and content of carboxylic acid represented by the following formula (2) R-COOH (2), wherein R represents an unsubstituted or substituted carbon chain having 1 to 10 carbon atoms, of 0.01 area% or less, or a manufacturing method therefor. SELECTED DRAWING: None COPYRIGHT: (C)2019,JPOandINPIT
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Paragraph 0036; 0037; 0038; 0039; 0040; 0041; 0042-0044
(2019/07/31)
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- Process for preparing fluorinated acids
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A process for the preparation a fluorinated acid of the formula RfCOOH, wherein the process includes the step of contacting: (i) a fluorinated alcohol of the formula RfCH2OH; and (ii) periodic acid; wherein each Rf is independently selected from linear, branched or cyclic hydrocarbyl of 1-12 carbon atoms having 1-25 fluorine atoms and any range there between; and wherein the contacting step is carried out in the presence of a catalyst and optionally in a reaction medium, at a temperature and length of time sufficient to produce the fluorinated acid.
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Page/Page column 3
(2008/06/13)
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- Ester compound, agent for controlling noxious organisms containing the same as active ingredient, and production intermediate thereof
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There is provided an ester compound represented by the formula I: STR1 wherein R1 is a methyl group or a hydrogen atom; R2 is a C1-6 haloalkyl group; and R3 is a pyrethroid acid residue, an agent for controlling noxious organisms containing the same as active ingredient and an intermediate for producing the same.
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- Ester compound, active agent for controlling noxious insect pests containing the same as active ingredient, intermediate for production of the ester compound, and process for producing the intermediate
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The present invention provides an ester compound represented by a formula I: STR1 wherein R1 denotes a hydrogen atom or a methyl group; R2 represents a 1-methyl-2-propenyl group, a 1-methyl-2-propynyl group, a 3,3-dihalogeno-1-methyl-2-propenyl group, or a C1 -C1 6 alkyl group which may be substituted with at least one halogen atom; and R3 represents an acid residue of pyrethroids. The invention also relates to an active agent for controlling noxious insect pests containing the ester compound as an active ingredient, an intermediate for production of the ester compound and a process for producing the intermediate. The ester compound represented by the formula I has good activities for controlling noxious insect pests.
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- Synthesis, Structure-Activity Relationships, and Pharmacological Evaluation of a Series of Fluorinated 3-Benzyl-5-indolecarboxamides: Identification of 4--1-methylindol-3-yl>methyl>-3-methoxy-N-benzamide, ...
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The continued exploration of a series of 3-(arylmethyl)-1H-indole-5-carboxamides by the introduction of fluorinated amide substituents has resulted in the discovery of 4--1-methylindol-3-yl>methyl>-3-methoxy-N-benzamide (38p, ZENECA ZD 3523), which has been chosen for clinical evaluation.This compound exhibited a Ki of 0.42 nM for displacement of LTD4 on guinea pig lung membranes, a pKB of 10.13 +/- 0.14 versus LTE4 on guinea pig trachea, and an oral ED50 of 1.14 μmol/kg opposite LTD4-induced bronchoconstriction in guinea pigs.The R enantiomer was found to be modestly more potent than the S enantiomer 38o.Modification of the amide substituent to afford achiral compounds was unsuccessful in achieving comparable levels of activity.Profiling of 38p opposite a variety of functional assays has demonstrated the selectivity of this compound as a leukotriene receptor antagonist.The enantioselective synthesis of 38p, which employed a diastereoselective alkylation of (4R,5S)-3-(1-oxo-4,4,4-trifluorobutyl)-4-methyl-5-phenyl-2-oxazolidinone (27) as the key step to establish the chirality of the amide substituent, provided an efficient route for generating 38p in >99percent enantiomeric purity.
- Jacobs, Robert T.,Bernstein, Peter R.,Cronk, Laura A.,Vacek, Edward P.,Newcomb, Lisa F.,et al.
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p. 1282 - 1297
(2007/10/02)
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- Chemical process for the preparation of 3-alkylated indole
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A process for the preparation of a 3-alkylated indole, which comprises: a) reacting a N-(2-nitrostyryl) enamine with an alkylating agent to afford an imine salt, b) optionally reacting the imine salt with water to afford a (2-nitrophenyl)acetaldehyde, and c) reacting the imine salt or the (2-nitrophenyl)acetaldehyde with a reducing agent capable of selectively reducing the nitro group, to afford the desired 3-alkylated indole.
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- Carbamoyl derivatives
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The present invention concerns novel carbamoyl derivatives of formula I, set out herein, which antagonize the pharmacological actions of one or more of the arachidonic acid metabolites known as leukotrienes, making them useful whenever such antagonism is desired, such as in the treatment of those diseases in which leukotrienes are implicated, for example, in the treatment of allergic or inflammatory diseases, or of endotoxic or traumatic shock conditions. The invention also provides pharmaceutical compositions containing the novel derivatives for use in such treatments, methods for their use and processes and intermediates for the manufacture of the novel derivatives.
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- CARBONYLATION OF 1-PERFLUOROALKYL-SUBSTITUTED 2-IODOALKANES CATALYZED BY TRANSITION-METAL COMPLEXES
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Carboxylic acids and esters with perfluoroalkyl substituent at β position were synthesized in good yields from 1-perfluoroalkyl-substituted 2-iodoalkanes and carbon monoxide with water or alcohols in the presence of base by using group VIII transition-metal complexes as catalysts.
- Urata, Hisao,Kosukegawa, Osamu,Ishii, Yoshimitsu,Yugary, Hideki,Fuchikami, Takamasa
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p. 4403 - 4406
(2007/10/02)
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- Structural Effects on the Transition States of Imine-Forming Eliminations in N-Substituted O-(Arylsulfonyl)hydroxylamines
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A series of amines with various alkyl and aryl substituents at C-1 were converted to the corresponding N-(arylsulfonoxy)amines, which served as precursors for base-promoted, imine-forming elimination.By varying the bases used to promote the elimination and by varying the leaving groups attached to nitrogen, the Broensted parameters β and βlgCH3 were determined.These were used to locate the transition state on the More O'Ferrall-Jencks energy surface for elimination.Substituents were found to influence the structure of the activated complex markedly.Resonance effects were most important, while inductive effects had little influence .
- Hoffman, Robert V.,Shankweiler, Jean M.
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p. 4019 - 4022
(2007/10/02)
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- Process for preparing pyrazolopyridine compounds
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Compounds of the formula (I): STR1 wherein R4 is hydrogen, D is oxygen or NR6, R1, R3, R6, R7 and R8 have defined values, and n is 1 or 2 are produced by internally cyclizing a compound of the formula (XV): STR2 wherein R19 is a value of R1 or hydrogen and, if R19 is hydrogen, reacting the cyclization product with R1 --Br and a weak base such as potassium carbonate.
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- CNS-Depressant pyrazolopyridines
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Compounds of the formula (I): STR1 wherein R1, R3, R4, R7 and R8 are as described herein, D is oxygen or NR6, n is 1 or 2 and the physiologically acceptable salts thereof useful in reducing anxiety in an animal such as man. The compounds are potent anxiolytics having reduced side effects compared to known anxiolytics. Also pharmaceutical compositions, intermediates and methods of treatment and synthesis are described.
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- Pyrazolo[3,4-b]pyridine carboxylic acid esters and their pharmaceutical use
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Compounds of the formula (I): STR1 wherein R1, R3, R4, R5 and R6 have defined values and the N-oxides at the 7-position of the pyrazolo[3,4-b]pyridine ring system and the pharmaceutically-acceptable acid-addition salts thereof, processes for their preparation and use, pharmaceutical compositions, and intermediates for preparing said compounds of the formula (I). The compounds of formula (I) are central nervous system depressants, for example anxiolytic agents.
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- Regioselective Hydroesterification and Hydrocarboxylation of 3,3,3-Trifluoropropene and Pentafluorostyrene Catalyzed by Phosphine-Palladium Complex
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The hydroesterification and hydrocarboxylation of 3,3,3-trifluoropropene (TFP) and pentafluorostyrene (PFS) catalyzed by phosphine-palladium complexes were studied.It was found that the efficiency and the product distribution of the reaction depended markedly on the nature of nucleophile, i. e., water or alcohol, the structures of olefin and phosphine ligand, and other reaction variables such as solvent, temperature, and carbon monoxide pressure.Under optimal conditions either unbranched products or branched products were obtained in high yields with high regioselectivities.For example, 4,4,4-trifluorobutyric acid (5a) was obtained in 93percent yield with 99percent regioselectivity by using PdCl2(dppf)-SnCl2 as the catalyst in the hydrocarboxylation of TFP while ethyl 2-methyl-3,3,3-trifluoropropionate (2a) was obtained in 96percent yield with 79percent regioselectivity in the hydroesterification of TFP by using PdCl2(PPh3)2 as the catalyst.Similarly, 3-(pentafluorophenyl)propionic acid (5b) was obtained in 93percent yield with 99percent regioselectivity in the hydrocarboxylation of PFS catalyzed by PdCl2(dppf), and methyl 2-(pentafluorophenyl)propionate (2b) was obtained in 89percent yield with 95percent regioselectivity in the hydroesterification of PFS catalyzed by PdCl2(PPh3)2.Possible mechanisms of the present reactions are discussed.The hydrocarboxylations of TFP and PFS may involve (hydroxycarbonyl)palladium(II) intermediates while the hydroesterifications of TFP and PFS may proceed via alkylpalladium(II) and acylpalladium(II) intermediates.
- Fuchikami, Takamasa,Ohishi, Katsuyuki,Ojima, Iwao
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p. 3803 - 3807
(2007/10/02)
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