- Industrialized synthetic method for halogen benzoic acid derivative
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The invention discloses an industrialized synthetic method for a halogen benzoic acid derivative. The formula (I) of the halogen benzoic acid derivative is shown in the description, wherein a plurality of Rs are alkyls of C1-C20, and a plurality of Xs are halogens; the industrialized synthetic method comprises the following steps that alkyl substituted benzoic acid and water are added into a reaction container, halogen simple substances are added, a heating reaction is performed, the reaction is complete, and post processing is performed to obtain the target product halogen benzoic acid derivative. According to the industrialized synthetic method for the halogen benzoic acid derivative, no solvent needs to be recycled, little consumption is consumed, little waste gas, water and industrialresidues are caused, and by-product haloid acid can be directly sold or used for producing other products; accordingly, the industrialized synthetic method for the halogen benzoic acid derivative is safe, environmentally friendly and low in cost, and therefore the wide industrial application prospect is achieved.
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Paragraph 0050; 0051; 0052; 0053; 0054; 0055; 0056; 0057
(2019/04/26)
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- Benzimidazol-2-yl or benzimidazol-2-ylthiomethyl benzoylguanidines as novel Na+/H+ exchanger inhibitors, synthesis and protection against ischemic-reperfusion injury
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A novel series of benzimidazol-2-yl or benzimidazol-2-ylthiomethyl benzoylguanidines were designed and synthesized as Na+/H+exchanger inhibitors. Most of them were found to inhibit NHE1-mediated platelet swelling in a concentration-dependent manner, and to have significant cardioprotective effect against myocardial ischemic-reperfusion injury, among which compounds 10a and 34 were more potent than cariporide in both in vivo and in vitro tests.
- Zhang, Rui,Lei, Lin,Xu, Yun-Gen,Hua, Wei-Yi,Gong, Guo-Qing
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p. 2430 - 2433
(2008/04/18)
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- Bromodecarbonylation and bromodecarboxylation of electron-rich benzaldehydes and benzoic acids with oxone and sodium bromide
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Benzaldehydes and benzoic acids bearing ortho- and paraelectron donating substituents having unshared electron-pair have undergone bromodecarbonylation or bromodecarboxylation on treatment with sodium bromide in the presence of Oxone in aqueous methanol.
- Koo, Bon-Suk,Kim, Eun-Hoo,Lee, Kee-Jung
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p. 2275 - 2286
(2007/10/03)
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- SYNTHESIS AND POLYMERIZATION OF 2,5-DISUBSTITUTED PHENYLACETYLENES CONTAINING TRIFLUOROMETHYL GROUPS
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Four phenylacetylenes (2-R2-5-R5-C6H3CCH : 1a R2=R5=CF3; 1b R2=CF3, R5=CH3; 1c R2=CH3, R5=CF3; 1d R2=R5=CH3) were synthesized via lithio compounds or Grignard reagent.Bromo(methyl)benzotrifluorides, the precursors for the lithio compounds, were prepared by the fluorination of the corresponding benzoic acids with sulfur tetrafluoride.Polymerization using transition metal catalysts provided polyacetylenes in high yields for all the monomers, while the yields of γ-ray induced polymerization depended on the monomers.The molecular weights of polyacetylenes have a positive correlation with the yields for all the polymerizations.The substituent effects on the molecular weights and tehrmal stabilities of polymers obtained were discussed.
- Nishida, Masakazu,Hosokawa, Kenzo,Ueda, Teruo,Aoki, Toshiki,Muramatsu, Hiroshige
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- CATALYTIC AND STOICHIOMETRIC BROMINATION OF AROMATIC COMPOUNDS IN AQUEOUS TRIFLUOROACETIC ACID IN THE PRESENCE OF NITROGEN-CONTAINING OXIDIZING AGENTS
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The mono- and polybromination of benzene, halogenobenzenes, toluene, p-xylene, anisole, biphenyl, benzotrifluoride, benzoic acid, p-nitro- and p-carboxytoluene, p-methoxybenzonitrile, tetralin, and naphtalene were studied in trifluoroacetic acid and its aqueous solutions in systems containing stoichiometric amounts of bromine or alkali-metal bromide and stoichiometric or catalytic (in the presence of oxygen or air) amounts of nitrogen-containing oxidizing agent (nitrogen(IV) oxide, alkali-metal nitrate or nitrite).It is suggested that the brominating agent under the investigated conditions is nitryl bromide NO2Br.Under the conditions of catalytic bromination anthracene is oxidized to anthraquinone with a preparative yield.
- Cheprakov, A. V.,Makhon'kov, D. I.,Rodkin, M. A.,Beletskaya, I. P.
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p. 217 - 223
(2007/10/02)
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- Preparation of dibenzo[b,f]thiepin compounds
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The preparation of dibenzo[b,f]thiepin compounds by a process comprising the direct carboxylation of an ortho-toluyl-aryl sulfide to introduce a phenylacetic acid side chain is disclosed.
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- CARBOXYLATION OF ARENES
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A two-step procedure for the carboxylation of aromatic rings is described, involving the intermediate preparation of 1-aryl-2,2,2-trichloroethanols (1), which form the corresponding benzoic acids by treatment with NaOH/H2O2.
- Menegheli, Paulo,Rezende, Marcos Caroli,Zucco, Cezar
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p. 457 - 464
(2007/10/02)
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- OXIDATION BY THE SALTS OF METALS. IV. OXIDATIVE HALOGENATION OF TOLUENE AND PARA-SUBSTITUTED TOLUENES WITH ELECTRON-WITHDRAWING GROUPS PROMOTED BY CERIUM(IV) SALTS IN AQEOUS SOLUTIONS OF TRIFLUOROACETIC ACID
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The oxidation of toluene and para-substituted toluenes with electron-withdrawing groups (para-toluic acid, methyl para-toluate, and para-nitrotoluene) by ammonium cerium(IV) nitrate and ammonium cerium(IV) sulfate was investigated in aqueous solutions of trifluoroacetic acid in the presence of alkali-metal chlorides and bromides.The rate and selectivity of oxidative halogenation in the side chain and/or aromatic ring under the investigated conditions depends strongly both on the nature of the substrate and the halide ion and on the reaction conditions and the ligand environment of the cerium(IV) atom.The oxidation of nitrotoluene takes place only in the presence of the bromide-containing systems and leads to the production of 4-nitrobenzyl bromide.For the other substrates halogenation in the aromatic ring can be realized with yields close to quantitative with ammonium cerium(IV) nitrate as oxidizing agent in concentrated aqueous solutions of trifluoroacetic acid (10 vol.percent of water).It was shown that the halogenating agents in this case are mainly the products from oxidation of the halide ions by the nitronium ions formed in the strongly acidic medium from the nitrate ions contained in the ammonium cerium(IV) nitrate.Bromination of the substituted toluenes in the presence of ammonium cerium(IV) sulfate and in the ammonium cerium(IV) nitrate-alkali-metal bromide systems with more than 10 vol.percent of water takes mainly in the side chain and can be used as a method for the production of 4-substituted benzyl halides with preparative yields.The effect of the composition of the solvent and the ratio of the oxidizing agent and alkali-metal halide on the rate and selectivity of oxidative bromination was studied.Possible reaction mechanisms are discussed.
- Makhon'kov, D.I.,Cheprakov, A.V.,Rodkin, M.A.,Mil'chenko, A.Yu.,Beletskaya, I.P.
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- Regioselective Diels-Alder Reactions. A Synthesis of the Left-Hand Portion of CC-1065
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Diene 2b reacted regioselectively with dienophiles.Adduct 6 was converted into the left-hand portion of CC-1065 in 10percent overall yield.
- Kraus, George A.,Yue, Stephen,Sy, James
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p. 283 - 284
(2007/10/02)
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- Oxidation by the salts of metals. I. Anaerobic oxidation of p-toluic acid by the salts of transition metals in trifluoroacetic acid in the presence of alkali-metal halides
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The oxidation of p-toluic acid by the salts of metals with variable valence was investigated in trifluoroacetic acid and its aqueous solutions in the presence of alkali-metal halides (chlorides or bromides).The reaction leads to the formation of the products from oxidative halogenation in the aromatic ring and/or the side chain.The rate and direction of the reaction depend both on the nature of the oxidizing agent and the halide ion and on the ratio of the components in the p-toluic acid-Hlg--CF3CO2H-H2O system.Preferential halogenation in the ring is observed for Ce(IV) and Pb(IV) in the presence of sodium bromide and for all the oxidizing agents in the presence of potassium chloride.In the case of Co(III) and Mn(III) bromination in the presence of Br- takes place mainly in the side chain and is greatly accelerated by additions of water.Conditions were found for the production of 3-chloro- and 3-bromo-p-toluic acid and 4-carboxybenzyl bromide with preparative yields.
- Beletskaya, I. P.,Dem'yanov, P. I.,Makhon'kov, D. I.,Zel'dis, I. M.,Burenko, S. N.
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p. 583 - 591
(2007/10/02)
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- Oxidation by the salts of metals. II. Anaerobic oxidation of 4-methylbenzoic acid by Co(III) acetate in the presence of sodium bromide in aqueous trifluoroacetic acid. Production of 4-hydroxymethylbenzoic acid
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The oxidation of 4-methylbenzoic acid by Co(III) acetate was investigated in aqueous solutions of trifluoroacetic acid in the presence of sodium bromide.The conditions were found for the production of 4-bromomethylbenzoic acid for the purpose of further h
- Beletskaya, I. P.,Dem'yanov, P. I.,Makhon'kov, D. I.,Zel'dis, I. M.
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p. 591 - 594
(2007/10/02)
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- ACCES AUX DINITRO-2,4 DIARYLAMINES PAR SUBSTITUTION NUCLEOPHILE SNAr-LIMITES DE LA REACTION ET APPLICATION A LA SYNTHESE DE CYANOCARBAZOLES
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3-Cyanocarbazoles, key-intermediates in the total synthesis of pyrido carbazoles, have been obtained starting from easily available materials and involving the cyclization of diarylamines.The first step of the preparation consists in a SNAr reaction between a para substituted aniline and a chloro- (or bromo)-dinitrobenzene.This nucleophilic substitution has been found to be hindered by the steric effect of a methyl group, explained in terms of inhibition of resonance and confirmed by X-ray determination.
- Henichart, J. P.,Bernier J. L.,Vaccher, C.,Houssin, R.,Warin, V.,Baert, F.
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p. 3535 - 3542
(2007/10/02)
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