- Novel preparation method of 3, 3, 3-trifluoropropionic acid
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The invention discloses a novel preparation method of 3, 3, 3-trifluoropropionic acid, and relates to the field of medical pesticides. 1, 1-dichloroethylene is used as a raw material to be subjected to an addition reaction with chloroformate or ester under the catalysis of iron powder to obtain trichloropropionate or salt thereof, the trichloropropionate or salt thereof is smoothly subjected to afluorination reaction under proper conditions to efficiently obtain trifluoropropionate or fluorine trifluoropropionate, and the trifluoropropionate or fluorine trifluoropropionate is hydrolyzed to obtain 3, 3, 3-trifluoropropionic acid. In conclusion, the method for preparing trifluoropropionic acid has the advantages of cheap and easily available initial raw materials, simple reaction operation,mild reaction conditions, few steps and high conversion rate, and the conversion rate of the raw material 1, 1-dichloroethylene exceeds 78%.
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Paragraph 0024; 0026; 0028; 0030; 0032; 0034-0036; 0038-0040
(2020/04/02)
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- Synthetic method of methyl 3,3,3-trifluoropropionate
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The invention discloses a preparation method of methyl 3,3,3-trifluoropropionate. The method is characterized in that methyl 3,3,3-trifluoropropionate is prepared from 3,3,3-trifluoropropionic acid and anhydrous methanol through carrying out a one step reaction at 60-100DEG C under magnetic stirring for 2-12h with a slightly soluble compound as a catalyst, The method has the characteristics of few steps, simple operation, environmental protection and high yield, and is suitable for industrial production.
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Paragraph 0011; 0024; 0025
(2016/11/17)
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- Method for producing 3, 3, 3 - [...] (by machine translation)
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PROBLEM TO BE SOLVED: To provide a simple, efficient and inexpensive method capable of manufacturing a 3,3,3-trifluoro propionyl compound useful as a pharmaceutical and agricultural synthetic intermediate in an industrial scale.SOLUTION: There is provided a method of manufacturing a compound represented by the formula [1] by reacting a compound represented by the formula [2] with a polar compound after hydrolysis with using sulfuric acid. In the formula [1], X is Cl, OH, ORor NRR, Ris a Cto Calkyl group, a Cto Chalogenated alkyl group or phenyl group, Rand Rmay be same or different and are each independently a hydrogen, a Cto Calkyl group, a Cto Chalogenated alkyl group or phenyl group and each may together form a ring structure.
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Paragraph 0059; 0060
(2019/10/19)
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- A 3, 3, 3-three fluorine third method of synthesizing acid methyl ester
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The invention discloses a method for synthesizing 3,3,3-trifluoro methyl propionate. The method comprises the following steps of: putting 3,3,3-trifluoropropene serving as a raw material, methyl alcohol, a Pd/C catalyst and a pro-oxidant in a reaction kettle, after introducing 3,3,3-trifluoropropene and oxygen gas, heating up to the temperature of 70-120 DEG C, reacting for 8-12 hours, cooling and filtering reacted liquid; and adding obtained filtrate, protonic acid and the pro-oxidant into a three-neck flask, heating up to the temperature of 60-80 DEG C, dropwise adding hydrogen peroxide, and reacting for 4-8 hours, thereby obtaining 3,3,3-trifluoro methyl propionate. The method has the advantages that the few synthesizing steps (only two steps) are carried out, the yield is high, and the after-treatment is simple.
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Paragraph 0031; 0033
(2017/04/04)
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- Bis-exo-2-norbornylboron triflate for stereospecific enolization of 3,3,3-trifluoropropionates
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The first boron-mediated enolization - aldolization of 3,3,3- trifluoropropionates has been reported. The preparation and application of bis-exo-bicyclo[2.2.1]heptan-2-ylboron triflate as a superior reagent for diastereospecific enolization has also been described.
- Ramachandran, P. Veeraraghavan,Parthasarathy, Gowrisankar,Gagare, Pravin D.
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supporting information; experimental part
p. 4474 - 4477
(2010/12/24)
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- Convenient synthesis of 3,3,3-trifluoropropanoic acid by hydrolytic oxidation of 3,3,3-trifluoropropanal dimethyl acetal
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A convenient and efficient method for preparing 3,3,3-trifluoropropanoic acid (1) is reported. The starting material is 1-chloro-3,3,3-trifluoropropene (2) that can be easily transformed into 3,3,3-trifluoropropanal dimethyl acetal (4) on treatment with methanol and KOH followed by acid-catalyzed addition of methanol. Direct transformation of 4 into 1 was efficiently achieved with 30% aqueous hydrogen peroxide (4.0 equiv.) in the presence of FeCl3 (0.025 equiv.) and hydrochloric acid (0.5 equiv.).
- Komata, Takeo,Akiba, Shinya,Hosoi, Kenji,Ogura, Katsuyuki
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- SELECTIVELY REACTING OLEFINS HAVING A TERMINAL CF2 GROUP IN A MIXTURE
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A process is disclosed for reducing the mole ratio of (1) compounds of the formula Y1Y2C=CF2 wherein Y1 and Y2 are each independently H, F, CI, Br, C1-C6 alkyl or C1-C6 haloalkyl containing no more than 3 chlorine substituents, 2 bromine substituents and 1 iodo substituent to (2) saturated compounds of the formula CdHeFfCIgBrhIk wherein d is an integer from 1 to 10, and e+f+g+h+k is equal to 2d+2, provided that g is 0, 1, 2 or 3, h is 0, 1 or 2 and k is 0 or 1 and/or unsaturated compounds of the formula Y3Y4C=CY5Y6, wherein Y3, Y5 and Y6 are each independently H, F, CI Br, C1-C6 alkyl or C1-C6 haloalkyl containing no more than 3 chlorine substituents, 2 bromine substituents and 1 iodo substituent, provided that Y5 and Y6 are not both F, and Y4 is C1-C6 alkyl or C1-C6 haloalkyl containing no more than 3 chlorine substituents, 2 bromine substituents and 1 iodo substituent, in a mixture. The process involves contacting the mixture with at least one selective removal agent selected from the group consisting of SO3 and RSO3H, wherein R is selected from the group consisting of F, CI, OH, C1-C8 alkyl, C1-C8 fluoroalkyl, and C1-C8 fluoroalkoxyalkyl containing no more than two ether oxygens to selectively react the formula Y1Y2C=CF2 compounds.
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- CHEMICAL COMPOUNDS
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The invention relates to chemical compounds of formula (I) and (II) or pharmaceutically acceptable salts thereof, which possess Edg-1 antagonistic activity and are accordingly useful for their anti cancer activity and thus in methods of treatment of the human or animal body. The invention also relates to processes for the manufacture of said chemical compounds, to pharmaceutical compositions containing them and to their use in the manufacture of medicaments of use in the production of an anti-cancer effect in a warm blooded animal such as man.
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Page/Page column 65
(2010/11/28)
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- Intramolecular 1,2-alkyl shifts in unsymmetric dialkoxycarbenes studied by very low vapour pressure (VLVP) pyrolysis - mass spectrometry
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Methoxy-(2,2,2-trifluoroethoxy)carbene radical cations, CH3O-C-OCH2CF3·+, 1·+, are cleanly generated by the dissociative electron ionization (EI) of 2-methoxy-5,5-dimethyl-2-(2, 2,2-trifluoroethoxy)-Δ3-1,3,4-oxadiazoline I. Neutralization-reionization (NR) mass spectrometry of the neutral carbene 1, generated by one-electron reduction of 1·+, shows no recovery ion signal and thus 1 is not a viable species within the μs time scale of the experiment. Very low vapour pressure (VLVP) pyrolysis - mass spectrometry of I in conjunction with (multiple) collision experiments shows that 1 completely isomerizes, via a 1,2-trifluoroethyl shift, into methyl 3,3,3-trifluoropropionate, CF3CH2C(=O)OCH3, 1a. This technique was also used to study the related dialkoxycarbenes C2H5O-C-OCH2CF3, 2, CH3O-C-OC2H5, 3, and CH3O-C-OCH(CH3)2, 4, generated from the corresponding 2,2-dialkoxy-5,5-dimethyl-Δ3-1,3,4-oxadiazolines. The pyrolytically generated carbene 2 behaves analogously to 1 and completely isomerizes to ethyl 3,3,3-trifluoropropionate, 2a. The neutral carbenes 3 and 4 undergo only a partial isomerization via 1,2-alkyl shifts in which the ethyl and isopropyl groups show a slightly greater migratory aptitude, respectively, than the methyl group. The differences in migratory aptitude are explained in terms of a transition state model similar to that of a 1,2-H shift in carbenes, with development of negative charge in the migrating group. The greater migratory aptitude of CF3CH2, as compared to CH3 and CH3CH2, is attributed to the stabilization of negative charge in the transition state by strongly electron-withdrawing β-fluorines whereas the differences in migratory aptitude between the alkyl groups in 3 and 4 are largely due to the greater polarizability of isopropyl and ethyl groups, as compared to the methyl group.
- Suh,Pole,Warkentin,Terlouw
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p. 544 - 548
(2007/10/03)
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- REACTION OF HYDROXY- AND CARBONYL COMPOUNDS WITH SULFUR TETRAFLUORIDE. XIV. REACTION OF ALIPHATIC OXOCARBOXYLIC ACIDS WITH SF4
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The reaction of mono- and dibasic 2-oxocarboxylic acids with sulfur tetrafluoride leads to loss of carbon monoxide.The resulting polyfluoroalkane products contain one less carbon atom than the starting oxoacid. 3-Oxopentanedioic and 4-oxopentanoic acids react with SF4 without cleavage of carbon-carbon bonds.Depending on the reaction conditions, the reaction products consist either of polyfluoroalkanes or acyl fluoride derivatives of fluorinated carboxylic acids.
- Bloshchitsa, F.A.,Burmakov, A.I.,Kunshenko, B.V.,Alekseeva, L.A.,Yagupol'skii, L.M.
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p. 1286 - 1291
(2007/10/02)
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- (TRIFLUOROMETHYL)KETENE SILYL ACETAL AS AN EQUIVALENT TO THE TRIFLUOROPROPIONIC ESTER ENOLATE: PREPARATION AND ALDOL-TYPE REACTIONS WITH ACETALS
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The title reagent, readily prepared from methyl β,β,β-trifluoropropionate with trimethylsilyl triflate, is shown to react with a broad variety of acetals to provide the corresponding α-CF3 β-alkoxy esters in good yields.
- Yokozawa, Tsutomu,Nakai, Takeshi,Ishikawa, Nobuo
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p. 3987 - 3990
(2007/10/02)
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