Ethers-buliding-blocks

1535-73-5,Some common heterocyclic compound, 1535-73-5, name is 3-Trifluoromethoxyaniline, molecular formula is C7H6F3NO, 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.

To an ice-salt bathcooled solution of 3 (7.65 g, 50.0 mmol), hydrochloric acid (150 mL), a solution of sodium nitrite (3.6 g, 50.0mmol, 50 mL/H2O) was added dropwise, the mixture was left to stir for 30 minutes, followed by addition of 3-trifluromethoxyalinine dissolved in 50 mL alcohol, and neutralized with sodium acetate, the mixture was stirredfor 2 hours while the reaction temperature was kept between -5 to 0 ¡ãC, before pouring into 2000 mL cold waterand stirring, the solid was filtered and washed with water until the filtrate was colorless, the crude productobtained was recrystallized with ethyl acetate to give 8.55 g 4 as orange-yellow solid (50percent).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 3-Trifluoromethoxyaniline, its application will become more common.

Reference:
Article; Fan, Yin-Bo; Li, Kun; Huang, Min; Cao, Yu; Li, Ying; Jin, Shu-Yu; Liu, Wen-Bing; Wen, Jia-Chen; Liu, Dan; Zhao, Lin-Xiang; Bioorganic and Medicinal Chemistry Letters; vol. 26; 4; (2016); p. 1224 – 1228;,
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A common heterocyclic compound, 22236-10-8, name is 4-(Difluoromethoxy)aniline, molecular formula is C7H7F2NO, 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. 22236-10-8.

Following General Procedure A, a solution of 4-difluoromethoxyaniline (0.50 g, 3.1 mmol) and (R)-3-(4-oxo-piperidin-1-yl)-butyronitrile (0.44 g, 2.6 mmol) in CH2Cl2 (10 mL), was treated with glacial AcOH (3 drops) and NaBH(OAc)3 (0.83 g, 3.9 mmol), stirring for 16 h at room temperature. Saturated aqueous NaHCO3 solution (15 mL) and 1N NaOH (2 mL) was added and the phases were separated and the aqueous extracted with CH2Cl2 (2¡Á15 mL). The combined organic extracts were dried (Na2SO4), filtered and concentrated under reduced pressure. The crude material was then purified by flash column chromatography on silica gel (1:1 EtOAc/CH2Cl2) to afford (R)-3-[4-(4-difluoromethoxy-phenylamino)-piperidin-1-yl]-butyronitrile as a white solid (0.61 g, 76%). 1H NMR (CDCl3) delta 1.20 (d, 3H, J=6.6 Hz), 1.43 (m, 2H), 2.06 (br d, 2H), 2.36 (m, 3H), 2.52 (m, 1H), 2.82 (m, 2H), 3.07 (sex, 1H, J=7.2 Hz), 3.24 (m, 1H), 6.36 (t, 1H, J=75 Hz), 6.54 (d, 2H, J=9.0 Hz), 6.95 (d, 2H, J=9.0 Hz).

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

Reference:
Patent; AnorMED Inc.; US2005/277668; (2005); A1;,
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1535-75-7, Adding some certain compound to certain chemical reactions, such as: 1535-75-7, name is 2-(Trifluoromethoxy)aniline, 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 1535-75-7.

General procedure: The general procedure for the preparation of (R)-2-amino-3,3,3-trifluoro-2-methyl-N-phenylpropanamide derivatives was as follows. Reactions were carried out according to the literature procedure reported by Zhichkin et al2 with slight modifications. The Vilsmeier reagent was prepared by adding oxalyl chloride (2.52 g, 19.8 mmol) dropwise to a solution of anhyd. DMF (1.50 g, 20.5 mmol) in CH2Cl2 (20 mL) at 0-5 ?C (CAUTION: Foaming.) and stirring at rt for 30 min. Compound 5 (1.93 g, 10.0 mmol) was added at 0 ?C to Vilsmeier reagent (20.0 mmol) in CH2Cl2 (20 mL) prepared as described above, and the mixture was stirred at rt for 2 h. At 0 ?C, a solution of substituted aniline (10.0 mmol) in CH2Cl2 (10 mL) was added, followed by DIPEA (5.30 g, 41.0 mmol), and the mixture was stirred for 1 h at rt. It was then concentrated to dryness, and the residue was heated at reflux in ethanol (25 mL) with ethylenediamine (2.70 g, 45.0 mmol) for 3 h. The resulting mixture was evaporated to dryness, stirred with water (50 mL) and partitioned between CH2Cl2 and water. The organic layer was dried (Na2SO4) and concentrated. The residue was purified by column chromatography (petroleum ether/ethyl acetate) to afford the desired compounds.

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 1535-75-7.

Reference:
Article; Li, Tian-Wen; Shang, Pei-Hua; Cheng, Chang-Mei; Zhao, Yu-Fen; Tetrahedron Letters; vol. 54; 2; (2013); p. 134 – 137;,
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3616-56-6, 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. 3616-56-6, name is 2,2-Diethoxy-N,N-dimethylethanamine, This compound has unique chemical properties. The synthetic route is as follows.

General procedure: Dimethylaminoacetaldehyde diethyl acetal (5 mmol) was added to a solution of 7 (0.5 mmol) in AcOH (5mL) at room temperature, and the mixture was heated at 100 ¡ãC. After 1 h, the mixture was gradually cooled to room temperature. The mixture was diluted with AcOEt (100 mL), washed with saturated NaHCO3 solution and brine, and dried over MgSO4. The solvent was removed, and the residue was separated by silica gel column chromatography with hexane/AcOEt (5:1) to give 3, 4 and 8.

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; Abe, Takumi; Ishikura, Minoru; Heterocycles; vol. 90; 1; (2015); p. 673 – 680;,
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14869-41-1, As we all know, there are many different methods for the synthesis of a compound, and people can choose the synthesis method that suits their own laboratory according to the actual situation. 14869-41-1 name is 2-(2-Chloroethoxy)acetic acid, This compound is widely used in many fields, so it is necessary to find a new synthetic route. The downstream synthesis method of this compound is introduced below.

90 ml toluene, lO.OOg 2-(2-chloroethoxy)acetic acid (X) oily extract obtained from one of the previous examples, 8.3 Ig 4-nitro-aniine and l .84g phenyl -boronic acid are measured into a 125 ml volume sulfonating flask equipped with a Dean-Stark attachment, a condenser and thermometer. The mixture is heated to the reflux temperature (1 10- 1 11 C), the reaction is checked by a TLC method. After the end of the reaction the mixture is cooled back, 1.00 ml ethylene-glycol is added. Then the mixture is heated again to the temperature of reflux, then it is refluxed for another half an hour. Then the mixture is cooled to a temperature of 0-5C. The suspension is filtered and washed with toluene. The filtrate is dried to a constant mass. The mass of the obtained pastel yellow powder: 12.98g, yield: 83%

At the same time, in my other blogs, there are other synthetic methods of this type of compound, 2-(2-Chloroethoxy)acetic acid, and friends who are interested can also refer to it.

Reference:
Patent; RICHTER GEDEON NYRT.; SZABO, Tamas; NEU, Jozsef; GARADNAY, Sandor; (17 pag.)WO2019/138362; (2019); A1;,
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As we all know, there are many different methods for the synthesis of a compound, and people can choose the synthesis method that suits their own laboratory according to the actual situation. 21702-84-1 name is 2,4-Dibromo-1-methoxybenzene, This compound is widely used in many fields, so it is necessary to find a new synthetic route. The downstream synthesis method of this compound is introduced below. 21702-84-1

(ii) 4-Methoxgammaisophthalonitrile 2,4-Dibromo-l -methoxybenzene (25 g, 0.094 mol; see step (i) above) was dissolved in dry DMF (50 mL). CuCN (25.3 g, 0.283 mol) was then added and the resulting mixture was stirred at 120C for 15 h, before being cooled to RT. The crude mixture was diluted with water and extracted with ethyl acetate. The organic layer was washed with water and brine, dried over anhydrous Na2SO4 and concentrated under reduced pressure. The residue was purified by column chromatography over silica gel, using 25% ethyl acetate in petroleum ether as eluent, to yield the sub-title compound (7.1 g, 24%) as pale yellow solid.

At the same time, in my other blogs, there are other synthetic methods of this type of compound, 2,4-Dibromo-1-methoxybenzene, and friends who are interested can also refer to it.

Reference:
Patent; ASTRAZENECA AB; WO2006/135316; (2006); A1;,
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458-52-6, A common compound: 458-52-6, name is 2-Fluoro-4-methoxyaniline, belongs to ethers-buliding-blocks compound, it can change the direction of chemical reaction, and react with certain compounds to generate new functional products. A new synthetic method of this compound is introduced below.

Step A 2-Fluoro-4-methoxyphenylhydrazine With vigorous stirring, 9.15 g (0.065 mole) of 2-fluoro-4-methoxyaniline (Example 3, Step B) was added to 60 mL of concentrated hydrochloric acid that had been cooled to -10¡ã C. A solution of 4.83 g (0.070 mole) of sodium nitrite in 30 mL of water was slowly added dropwise, while the temperature was kept at or below -10¡ã C. Upon completion of addition, the reaction mixture was stirred at -10¡ã C. for one hour, after which 33.85 (0.150 mole) of tin(II) chloride dihydrate in 50 mL of concentrated hydrochloric acid Was added slowly, dropwise, while the temperature was kept below -5¡ã C. After the reaction mixture had stirred for one hour as it warmed to ambient temperature, the crude product was filtered from the mixture and dissolved in 250 mL of water. This solution was made basic with 4N sodium hydroxide and extracted with methylene chloride. The combined extracts were dried over anhydrous sodium sulfate and filtered. The filtrate was placed on a silica gel column and eluted with methylene chloride to remove colored impurities and then with ethyl acetate to obtain the desired product. The solvent was evaporated under reduced pressure to yield 6.30 g of 2-fluoro-4-methoxyphenylhydrazine. The NMR spectrum was consistent with the proposed structure.

In the field of chemistry, the synthetic routes of compounds are constantly being developed and updated. I will also mention this compound in other articles, 2-Fluoro-4-methoxyaniline, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; FMC Corporation; US5262390; (1993); A;,
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Ether | (C2H5)2O – PubChem

1484-26-0, A common heterocyclic compound, 1484-26-0, name is 3-Benzyloxyaniline, molecular formula is C13H13NO, 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.

B. 3-Benzyloxyphenyl isocyante. To a stirred solution of 3-benzyloxyaniline (507 mg, 2.54 mmol) in toluene (5 mL) containing TEA (740 muL, 5.34 mmol) was added 20percent phosgene in toluene (1.5 mL, 2.83 mmol). The reaction was stirred for 20 h at rt. The organic layer was washed with H2O (20 mL), dried (MgSO4) and concentrated to give a clear brown oil (497 mg, 87percent). The material was used in subsequent steps without charaterization.

The synthetic route of 1484-26-0 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Butler, Christopher R.; Edwards, James P.; Fourie, Anne M.; Grice, Cheryl A.; Karlsson, Lars; Savall, Brad M.; Tays, Kevin L.; Wei, Jianmei; US2006/223792; (2006); A1;,
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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. 583-19-7, name is 1-Bromo-2-ethoxybenzene, This compound has unique chemical properties. The synthetic route is as follows., 583-19-7

3-(2-bromoacetyl)-8-chloro-2H-chromen-2-one (150 mg, 0.54 mmol) and l-bromo-2-ethoxybenzene (108 mg, 0.54 mmol) were reacted in a microwave in the presence of CS2CO3 (528 mg, 1.62 mmol), Pd2(dba)3 (40mg, 0.054mmol.), xantphose (60mg, 0.108mmol), and dioxane (2 mL) at 160C for 15 minutes. The resulting product was then purified by pre-HPLC to yield 8-chloro-3-(2-(2-ethoxyphenylamino)thiazol-4-yl)-2H-chromen-2-one (20 mg, 10%) as a yellow solid. ESI-MS (EI+, m/z): 399.1 [M+l]+; 1HNMR (500 MHz, DMSO-<): delta 1.40 (t, J = 7 Hz, 3H), 4.14 (q, J= 7 Hz, 2H), 6.99-7.05 (m, 3H), 7.39 (t, J = 8 Hz, 1H), 7.76-7.79 (m, 2H), 7.93 (t, J= 7 Hz, 1H), 8.48-8.49 (m, 1H), 8.65 (s, 1H), 9.54 (s, 1H). 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; DISCOVERYBIOMED, INC.; SCHWIEBERT, Erik; STREIFF, John; DIXON, John; GAO, Hongwu; WO2014/152213; (2014); A2;,
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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. 41406-00-2, name is 3-Isopropoxyaniline, A new synthetic method of this compound is introduced below., 41406-00-2

General procedure: 3-Hydroxynaphthalene-2-carboxylic acid (5.3 mmol) and the appropriate alkoxyaniline (5.3 mmol) were suspended in dry chlorobenzene (25 mL). Phosphorous trichloride (0.23 mL, 2.7 mmol) was added dropwise, and the reacting mixture was heated in the microwave reactor at maximal allowed power 500 W and 130C, using infrared flask-surface control of temperature, for 15 min. The solvent was evaporated under reduced pressure and the solid residue washed with 50 mL of 2 M HCl. The crude product was recrystallized from aqueous ethanol.

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:
Article; Gonec, Tomas; Zadrazilova, Iveta; Nevin, Eoghan; Kauerova, Tereza; Pesko, Matus; Kos, Jiri; Oravec, Michal; Kollar, Peter; Coffey, Aidan; O’Mahony, Jim; Cizek, Alois; Kralova, Katarina; Jampilek, Josef; Molecules; vol. 20; 6; (2015); p. 9767 – 9787;,
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