Category: ethers-buliding-blocks

29578-83-4, Researchers who often do experiments know that organic synthesis is a process of preparing more complex target molecules from simple raw materials through one or more chemical reactions. Generally, it requires fewer steps, and cheap raw materials. 29578-83-4, name is 1-Bromo-3-methoxy-5-methylbenzene, A new synthetic method of this compound is introduced below.

A mixture of 5-bromo-3-methoxytoluene (20 g, 0.1 m), N-bromosuccinimide (17.8 g, 0.1 m) and dibenzoyl peroxide in carbon tetrachloride (200 ml) is heated to reflux and irradiated with a sunlamp. The mixture is cooled, filtered and concentrated in vacuo to give 5-bromo-3-methoxybenzyl bromide.

The basis of chemical reaction formula synthesis, the synthesis route is composed of some specific reactions and combined according to certain logical thinking. We look forward to the emergence of more reaction modes in the future.

Reference:
Patent; SmithKline Beckman Corporation; US4824839; (1989); A;,
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51388-20-6, In the next few decades, the world population will flourish. As the population grows rapidly and people all over the world use more and more resources, all industries must consider their environmental impact. 51388-20-6, name is 4-(Benzyloxy)aniline hydrochloride belongs to ethers-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below.

Intermediate 29: 6-(at) f 2-((at)2- f (2-aminoethyl)oxyl ethyl(at) oxy)ethyll oxy)-1-ethyl-4-oxo-1,4-dihydro-3- quinolinecarboxylic acid formate a) Ethyl 4-oxo-6-[(phenylmethyl)oxy]-1,4-dihydro-3-quinolinecarboxylate p-Benzyloxy aniline hydrochloride (25 g) was shaken with 1M NaOH (120 mL) and diethyl ether (200 mL). The organic layer was washed with brine, dried (MgS04) and evaporated to a solid (21.3 g). This material was heated with ethoxymethylene malonate (27.9 g) at 130C for 1.5 h using a Dean and Stark condenser. Dowtherm (100 mL) was added and the mixture heated to 250C using a Dean and Stark condenser for 70 min. The mixture was cooled and treated with petroleum ether (bp 60-80C) to precipitate a brown solid. This was slurried in dichloromethane, the pale yellow solid was filtered and dried to give the title compound (11.06 g). (at)H-NMR(400 MHz, DMSO-d6) No.: 1.28 (3H, t, J = 7.2 Hz), 4.21 (2H, q, J = 7.2 Hz), 5.21 (2H, s), 7.3 (1H, m), 7.4 (3H, m), 7.4 (2H, m), 7.59 (1H, d, J=8.8 Hz), 7.66 (1H, d, J= 2.8 Hz) , 8.49 (1H, s) and 12.3 (lH, br).

The synthetic route of 4-(Benzyloxy)aniline hydrochloride has been constantly updated, and we look forward to future research findings.

Reference:
Patent; PLIVA-ISTRAZIVACKI INSTITUT D.O.O.; WO2005/108413; (2005); A1;,
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1535-73-5, A common heterocyclic compound, 1535-73-5, name is 3-Trifluoromethoxyaniline, molecular formula is C7H6F3NO, its traditional synthetic route has been very mature, but the traditional synthetic route has various shortcomings, such as complicated route, low yield, poor purity, etc, below Introduce a new synthetic route.

A mixture of a-7 (0.001 mol), meta- (OCF3)-aniline (0.0015 mol), supported cyano-borohydride (0.0021 mol) and acetic acid (6 drops) in methanol was stirred at room temperature for 48 hours, and then filtered. The filtrate was evaporated. The residue was taken up in CH2Cl2/methanol. The organic layer was washed with a solution of K2C03 10percent, dried over magnesium sulfate, filtered and the solvent was evaporated. The residue (0.42g) was purified by column chromatography over silica gel (eluent: CH2Ck/CH30H/NH4OH 93/7/0. 5 ; 15-35 pm). The pure fractions were collected and the solvent was evaporated. The residue (0. 15g, 32percent) was crystallized from CH3CN/methanol. The precipitate was filtered off and dried, yielding 0.085g (18percent, compound 4, melting point: 156¡ãC) of 2-{2-Amino-6-[(3-trifluoromethoxy- phenylamino)-methyl]-benzoimidazol-1-ylmethyl}-6-methyl-pyridin-3-ol.

The synthetic route of 1535-73-5 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; TIBOTEC PHARMACEUTICALS LTD.; WO2005/58869; (2005); A1;,
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767-91-9, In the chemical reaction process, reaction time, type of solvent, can easily affect the result of the reaction, thereby determining the yield and properties of the reaction product. An updated downstream synthesis route of 767-91-9 as follows.

General procedure: A mixture of aldehyde (1.97 mmol), amine (1.97 mmol), acetylene (2.95 mmol), and thecorresponding supported Au catalyst (1% wt, 60 mg, 0.002 mmol) was heated at 60 C for 8 h,after which time the solution was cooled and the catalyst was removed by filtration. The filtrate wasevaporated under reduced pressure to afford propargylamine 5. Yields were determined by integration of the 1H-NMR spectra of the crude reaction mixtures. After separation and washing with n-pentane,the catalyst was reused intact for the next reaction without any further pre-treatment.

According to the analysis of related databases, 2′-Methoxyphenyl acetylene, the application of this compound in the production field has become more and more popular.

Reference:
Article; Soengas, Raquel; Navarro, Yolanda; Iglesias, Maria Jose; Lopez-Ortiz, Fernando; Molecules; vol. 23; 11; (2018);,
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5961-59-1, Each compound has different characteristics, and only by selecting the characteristics of the compound suitable for a specific situation can the compound be applied on a large scale. 5961-59-1, name is 4-Methoxy-N-methylaniline, This compound has unique chemical properties. The synthetic route is as follows.

General procedure: A round-bottomed flask was charged with the aryl halide (1 mmol),the indoline or (het)aryl amine (1 mmol), and Pd2(dba)3 (0.005mmol, 5 mg). At this point, CH2Cl2 (10 mL) was used to dissolve the reactants and to suspend K2CO3 (4 mmol, 552 mg) and Al2O3 (2g). The CH2Cl2 was then removed under reduced pressure and subsequently recovered. The residual powder was ground with a mortar and pestle for 5 min. A microwave oven reactor was charged with the reactant powder which was compacted as much as possible. The powder was heated at 140 ¡ãC for 20 min at medium power (350 W) ,then charged into a flash silica gel column which was eluted with hexane?EtOAc (4:1) to give the purified product. The solid products were further purified by crystallization from hexane?Et2O.

If you are interested in these compounds, you can also browse my other articles.Thank you for taking the time to read this article. I hope you enjoyed it.

Reference:
Article; Basolo, Luca; Bernasconi, Alice; Broggini, Gianluigi; Gazzola, Silvia; Beccalli, Egle M.; Synthesis; vol. 45; 22; (2013); p. 3151 – 3156;,
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Some common heterocyclic compound, 64115-88-4, name is 1-Bromo-2-(trifluoromethoxy)benzene, molecular formula is C7H4BrF3O, traditional synthetic route has been very mature, but the traditional synthetic route has various shortcomings, such as complicated route, low yield, poor purity, etc, below Introduce a new synthetic route. 64115-88-4

Preparation of (2-[trifluoromethoxylphenyl)fphenyl)phosphine chloride To a flame dried Schlenk tube containing magnesium turnings (0.15 g, 6.22 mmo) in anhydrous THF (7 mi) was added 1-bromo-2- [trifluoromethoxy] benzene (1.0 g, 4.14 mmo). An exothermic reaction ensued. Stirring was continued at room temperature. Once the reaction exotherm had dissipated, the reaction mixture was used in the next step as described beiow: The Grignard reagent (separated from excess Mg) was incrementally added to a solution of PhPCI2 (0.74 g, 4.14 mmol) in anhydrous THF (10 ml) at -78C. Once addition was complete, the reaction was stirred at room temperature for a further 20 min after which the reaction was complete as judged by 3 P NMR ( 1P NMR (CDCIs): delta 72.27 (m); 61.81 (m)). The product was used in the next step without further purification.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 64115-88-4, its application will become more common.

Reference:
Patent; SASOL TECHNOLOGY (PROPRIETARY) LIMITED; MOGOROSI, Moses Mokgolela; MAUMELA, Munaka Christopher; OVERETT, Matthew James; WO2014/181248; (2014); A1;,
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A common heterocyclic compound, 437-83-2, name is 3-Fluoro-2-methoxyaniline, molecular formula is C7H8FNO, its traditional synthetic route has been very mature, but the traditional synthetic route has various shortcomings, such as complicated route, low yield, poor purity, etc, below Introduce a new synthetic route. 437-83-2.

Step D: 1-bromo-3-fluoro-2-methoxybenzene: NaN02 (12.0 g, 173 mmol, in 40 mL of water)solution was added dropwise to the mixture of 3-fluoro-2-methoxyaniline (20.0 g, 158 mmol) in 200 mL of hydrobromic acid ( 4 7 %) and 100 mL of water at -5 ~ 0 C and stirred for 1 hour.This solution was then added slowly to the suspension ofCuBr (45.2 g, 315 mmol) in 50 mL ofhydrobromic acid (47 %) at 0 C. The resulting mixture was stirred at 0 C for 1 hour thenwarmed to 50 C and stirred for 1 hour. The reaction mixture was poured into ice water and extracted with ether (2 X 500 mL). The combined organic layer was washed with brine, driedover anhydrous Na2S04 and concentrated to give 1-bromo-3-fluoro-2-methoxybenzene.

The synthetic route of 3-Fluoro-2-methoxyaniline has been constantly updated, and we look forward to future research findings.

Reference:
Patent; MERCK SHARP & DOHME CORP.; PASTERNAK, Alexander; BLIZZARD, Timothy; CHOBANIAN, Harry; DE JESUS, Reynalda; DING, Fa-Xiang; DONG, Shuzhi; GUDE, Candido; KIM, Dooseop; TANG, Haifeng; WALSH, Shawn; PIO, Barbara; JIANG, Jinlong; WO2013/28474; (2013); A1;,
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710-18-9, The chemical industry reduces the impact on the environment during synthesis 710-18-9, name is 1-Methoxy-4-(trifluoromethoxy)benzene, I believe this compound will play a more active role in future production and life.

PREPARATION 18 2-Methoxy-5-trifluoromethoxybenzoyl chloride Combine 2-methoxy-5-trifluoromethoxybenzene (1.0 g, 5.2 mmol) and trifluoroacetic acid (200 mL). Add slowly portionwise hexamethylenetetraamine (26 g, 185.7 mmol). Heat at 60 C. After 24 hours, cool to ambient temperature and pour the reaction mixture into a 2M aqueous solution of sulfuric acid (500mL). Cool and extract ten times with diethyl ether. Dry the combined organic layers over Na2 SO4, filter, and evaporate in vacuo to give a residue. Chromatograph the residue on silica gel eluding with 1/4 ethyl acetate/hexane to give 2-methoxy-5-trifluoromethoxybenzaldehyde.

The chemical industry reduces the impact on the environment during synthesis 1-Methoxy-4-(trifluoromethoxy)benzene. I believe this compound will play a more active role in future production and life.

Reference:
Patent; Hoechst Marion Roussel, Inc.; US5922737; (1999); A;,
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Adding some certain compound to certain chemical reactions, such as: 6346-09-4, name is 4,4-Diethoxybutan-1-amine, can increase the reaction rate and produce products with better performance than those obtained under traditional synthetic methods. Here is a downstream synthesis route of the compound 6346-09-4. 6346-09-4

To a solution of [4,4-bis(ethyloxy)butyl]amine (5.0 g, 30.0 mmol) and Et3N (4.61 ml, 33.0 mmol) in 40 ml_ of THF was added ethyl 1 ,3-dioxo-1 ,3-dihydro-2/-/-isoindole-2- carboxylate (6.9 g, 32.0 mmol). The mixture was stirred overnight at room temperature. The reaction mixture was concentrated in vacuo and the residue was extracted with hexane. The hexane solution was concentrated in vacuo and heated at 100 0C under reduced pressure to remove ethylcarbamate by sublimation. The mixed solution of diethyl acetal (2.0 g, 6.95 mmol) thus obtained and 1 Lambda/aq. HCI (14 ml_) in acetone (20 ml_) was heated under reflux for 15 min. Acetone was evaporated and aqueous layer was extracted with ether, dried over MgSO4, and filtered. The solvent was evaporated and the residue was moved to next step.

Chemical properties determine the actual use. Each compound has specific chemical properties and uses. We look forward to more synthetic routes in the future to expand reaction routes of 4,4-Diethoxybutan-1-amine.

Reference:
Patent; SMITHKLINE BEECHAM CORPORATION; WO2007/30761; (2007); A2;,
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366-99-4, Each compound has different characteristics, and only by selecting the characteristics of the compound suitable for a specific situation can the compound be applied on a large scale. 366-99-4, name is 3-Fluoro-4-methoxyaniline, This compound has unique chemical properties. The synthetic route is as follows.

28.a. 1-(2-amino-4-fluoro-5-methoxyphenyl)-1-propanone (This product is obtained according to Sugasawa T; Toyoda T; Adachi M; Sasakura K, J Am. Chem. Soc., 100 (1978), p.4842-4852). Boron trichloride (1M in heptane, 156 ml, 156 mmol) is added dropwise, under an argon atmosphere at 0¡ã C. to a solution of 3-fluoro-4-methoxy-aniline (20 g, 142 mmol) in anhydrous dichloromethane (200 ml). The pink suspension thus obtained is maintained under agitation for 5 minutes, then propionitrile (33 ml, 420 mmol) is added dropwise followed by aluminium trichloride (20.8 g, 156 mmol) in small portions. The reaction medium is heated under reflux for 3 hours, cooled down to 0¡ã C., hydrolyzed by cautiously adding 2N hydrochloric acid (100 ml), then heated at reflux for 45 minutes. After cooling down to 0¡ã C. a precipitate is obtained which is filtered out, washed with dichloromethane, then taken up in water (300 ml). The aqueous phase is basified to an alkaline pH, extracted with dichloromethane then ethyl acetate. The organic phase is dried (MgSO4) then evaporated to produce a crude product which is purified by column chromatography (SiO2, AcOEt/Hpt: 1/99 to 20/80). 15.3 g of a yellow solid is obtained. NMR-1H (CDCl3): 1.20 (t, 3H); 2.92 (q, 2H); 3.83 (s, 3H); 6.2 (s, 2H); 6.40 (d, 2H); 7.32 (d, 2H). IR(KBr): 857; 1148; 1240; 1561; 1583; 1662.

If you are interested in these compounds, you can also browse my other articles.Thank you for taking the time to read this article. I hope you enjoyed it.

Reference:
Patent; Bigg, Dennis; Lavergne, Olivier; Pla Rodas, Francesc; Pommier, Jacques; Ulibarri, Gerard; Harnett, Jerry; Rolland, Alain; Liberatore, Anne-Marie; Lanco, Christophe; Cazaux, Jean-Bernard; Le Breton, Christine; Manginot, Eric; US2003/4150; (2003); A1;,
Ether – Wikipedia,
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