Ethers-buliding-blocks

22236-08-4, 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 22236-08-4 as follows.

Reference Example 353-{[3-(Difluoromethoxy)phenyl]hydrazono}pentane-2,4-dione To a solution of 3-(difluoromethoxy)aniline (1000 mg, 6.25 mmol) in 10 mL of acetic acid and 2 mL of concentrated hydrochloride solution, sodium nitrite (518 mg, 7.50 mmol) in 4 mL of water was added dropwise at 0 C., and the mixture was stirred at 0 C. for 1 h. Then to the reaction mixture was added dropwise a solution of sodium acetate (1538 mg, 18.75 mmol) and acetylacetone (812 mg, 8.12 mmol) in 10 mL of ethanol and 6 mL of water. The mixture was stirred at room temperature overnight, filtered, washed with water, EtOH/H2O (1:1) and hexane, and dried to give 3-{[3-(difluoromethoxy)phenyl]hydrazono}pentane-2,4-dione (1500 mg, 89%).LCMS: m/z=271 [M++H].

According to the analysis of related databases, 3-(Difluoromethoxy)aniline, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Taniguchi, Takahiko; Kawada, Akira; Kondo, Mitsuyo; Quinn, John F.; Kunitomo, Jun; Yoshikawa, Masato; Fushimi, Makoto; US2010/197651; (2010); A1;,
Ether – Wikipedia,
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5473-01-8, Name is 2-Bromo-6-methoxyaniline, 5473-01-8, belongs to ethers-buliding-blocks compound, is considered to be a conventional heterocyclic compound, which is widely used in drug synthesis. The chemical synthesis route is as follows.

To a solution of 2-bromo-6-methoxyaniline (AK-90829) (1.000 mL, 7.55 mmol) in tetrahydrofuran (10 mL) was added Pd-PEPPSI-IPent-Cl (dichloro[1,3-bis(2,6-di-3-pentylphenyl)imidazol-2-ylidene](3-chloropyridyl)palladium(II), 0.208 g, 0.242 mmol). Nitrogen was bubbled through the solution for about 3 minutes, then a 0.4 M in tetrahydrofuran solution of isopropylzinc(II) bromide (52 mL, 20.80 mmol) was added dropwise over 5 minutes, with nitrogen flushing through the system and the internal temperature rising slowly from 21¡ã C. to 32¡ã C. The reaction mixture was stirred for 15 hours at ambient temperature, at which point it was quenched with saturated aqueous ammonium chloride (50 mL), diluted with methyl tert-butyl ether (400 mL), and the layers were separated. The organic layer was filtered through a pad of silica gel and concentrated in vacuo. The crude material was purified via flash chromatography, eluting on a 40 g silica gel cartridge with 1-40percent ethyl acetate/heptanes over 40 minutes to provide the title compound. 1H NMR (400 MHz, chloroform-d) delta ppm 6.89-6.66 (m, 3H), 3.87 (s, 3H), 3.86 (s, 2H), 2.96 (hept, J=6.8 Hz, 1H), 1.28 (d, J=6.9 Hz, 6H)+

Statistics shows that 2-Bromo-6-methoxyaniline is playing an increasingly important role. we look forward to future research findings about 5473-01-8.

Reference:
Patent; AbbVie S.a.r.l.; Galapagos NV; Altenbach, Robert J.; Bogdan, Andrew; Couty, Sylvain; Desroy, Nicolas; Gfesser, Gregory A.; Housseman, Christopher Gaetan; Kym, Philip R.; Liu, Bo; Mai, Thi Thu Trang; Malagu, Karine Fabienne; Merayo Merayo, Nuria; Picolet, Olivier Laurent; Pizzonero, Mathieu Rafael; Searle, Xenia B.; Van der Plas, Steven Emiel; Wang, Xueqing; Yeung, Ming C.; (189 pag.)US2019/77784; (2019); A1;,
Ether – Wikipedia,
Ether | (C2H5)2O – PubChem

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. 6876-00-2 name is 1-Bromo-3-phenoxybenzene, 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. 6876-00-2

EXAMPLE 20 2-Fluoro-4-methyl-1-(3-phenoxyphenyl)-4-(4-trifluoromethoxyphenyl)pent-2-ene The method of Example 16 was repeated using a Grignard reagent, prepared from 3-phenoxyphenyl bromide (0.3 g), tetrahydrofuran (2 ml) and magnesium (22 mg), and 2-fluoro4-methyl-4-(4-trifluoromethoxyphenyl)pent-2-enyl acetate (Example 15) (0.1 g). The residue after evaporation was purified by preparative thin layer chromatography (solvent: diethyl ether/hexane; 1:9) to give the title compound (56 mg, 42%).

At the same time, in my other blogs, there are other synthetic methods of this type of compound, 1-Bromo-3-phenoxybenzene, and friends who are interested can also refer to it.

Reference:
Patent; British Technology Group, Ltd.; US5880162; (1999); A;,
Ether – Wikipedia,
Ether | (C2H5)2O – PubChem

Adding a certain compound to certain chemical reactions, such as: 458-50-4, name is 4-Bromo-3-fluoroanisole, belongs to ethers-buliding-blocks compound, 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 458-50-4, 458-50-4

l-bromo-2-fluoro-4-methoxybenzene (750 mg, 3.658 mmol), potassium acetate (718 mg, 7.32 mmol), l,l’-bis(diphenylphosphino) ferrocene-palladium dichloride dichloromethane adduct (300 mg, 0.367 mmol), bis(pinacolato)diboron (984 mg, 4.39 mmol) and 1,4-dioxane (10 ml) were sealed and subject to microwave irradiation at 140 ¡ãC for a total of 50 minutes (40 min + 10 min). LCMS of aliquot indicated complete consumption of starting material. The reaction crude was filtered through a pad of Celite (521). The filtrate was worked up with brine, extracted with ethyl acetate, dried over Na2SO4, filtered and evaporated to afford a dark oil as the crude mixture of the title compound. To be used as it was for next step. LCMS (ESI) calc. = 252.13; found = 253.09 (M+l)+.

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, 4-Bromo-3-fluoroanisole, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; MERCK & CO., INC.; WO2007/79186; (2007); A2;,
Ether – Wikipedia,
Ether | (C2H5)2O – PubChem

60792-79-2, 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 60792-79-2 as follows.

In a typical run, sodium hydroxide (400 mg, 10 mmol) is dissolved in MeOH (70 mL) and 2-(2-aminoethoxy)ethanamine dihydrochloride (1.0 g, 5.65 mmol) is added. The resulting reaction mixture is stirred at room temperature for 30 min. A solution containing Boc2O (740 mg, 3.40 mmol) in THF (15 mL) is then added dropwise, at room temperature, over a period of 15 min. The resulting reaction mixture is stirred at room temperature for 18 h. It is then concentrated under reduced pressure. The resulting residue is taken up in CH2Cl2 (200 mL) and stirred vigorously at room temperature for 4 h. The mixture is filtered and the filtrate is concentrated under reduced pressure to afford tert-butyl 2-(2-aminoethoxy)ethylcarbamate.

According to the analysis of related databases, 2,2′-Oxybis(ethylamine) dihydrochloride, the application of this compound in the production field has become more and more popular.

Reference:
Patent; CATABASIS PHARMACEUTICALS, INC.; US2012/252810; (2012); A1;,
Ether – Wikipedia,
Ether | (C2H5)2O – PubChem

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. 22236-10-8, name is 4-(Difluoromethoxy)aniline belongs to ethers-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below. 22236-10-8

General procedure: Commercially available substituted aniline (63.4mmol) was portionwise added to a solution of concentrated HCl (13mL), ethanol (20mL) and water (7mL). To the above mixture was added dropwise a solution of NaNO2 (4.69g, 69.7mmol) in water (15mL) at 0-5C. After the completion of addition, the reaction mixture was stirred at this temperature for 30min, and then added into a mixture of ethyl 2-chloroacetoacetate (10.88g, 63.4mmol), anhydrous sodium acetate (15.60g, 190.10mmol), and water (90mL) at 0C. The reaction mixture was stirred at 0C for 10min and then at room temperature for 4h. The solid which precipitated was collected by filtration and recrystallized from ethanol to afford light yellow solids (21a-21m) in 75.2-90% yields. 6.3.3 Ethyl 2-chloro-2-(2-(4-(difluoromethoxy)phenyl)hydrazono)acetate (21c) Yellow solid; Yield: 78.9%; M.p.: 120.8-121.6 C; MS (ESI) m/z(%): 315.1 [M+Na]+.

The synthetic route of 22236-10-8 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Liu, Ju; Nie, Minhua; Wang, Yanjing; Hu, Jinxing; Zhang, Feng; Gao, Yanlin; Liu, Yajing; Gong, Ping; European Journal of Medicinal Chemistry; vol. 123; (2016); p. 431 – 446;,
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2752-17-2, 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. 2752-17-2, name is 2,2′-Oxydiethanamine, A new synthetic method of this compound is introduced below.

Example 189Preparation of rac-(2R,3R,4R,5S)-3-(3-chloro-phenyl)-4-(4-chloro-phenyl)-4-cyano-5-(2,2-dimethyl-propyl)-pyrrolidine-2-carboxylic acid [2-(2-amino-ethoxy)-ethyl]-amide; A mixture of rac-(2R,3R,4R,5S)-3-(3-chloro-phenyl)-4-(4-chloro-phenyl)-4-cyano-5-(2,2-dimethyl-propyl)-pyrrolidine-2-carboxylic acid (86.2 mg, 0.20 mmol), 2,2′-oxybis(ethylamine) (31.3 mg, 0.3 mmol), 2-(7-azabenzotriazol-1-yl)-n,n,n’,n’-tetramethyluronium hexafluorophosphate (HATU, 76 mg, 0.2 mmol) and iPr2NEt (0.1 mL, 0.55 mmol) in CH2Cl2 (2 mL) was stirred at rt overnight. The mixture was then diluted with CH2Cl2 and washed with water, brine. The organic phase was separated, filtered and dried over Na2SO4. The mixture was then concentrated and purified by reverse phase chromatography (20-95% of ACN/water) to give rac-(2R,3R,4R,5S)-3-(3-chloro-phenyl)-4-(4-chloro-phenyl)-4-cyano-5-(2,2-dimethyl-propyl)-pyrrolidine-2-carboxylic acid [2-(2-amino-ethoxy)-ethyl]-amide (20.3 mg, 19.6%) as an off-white powder. HRMS (ES+) m/z Calcd for C27H34Cl2N4O2+H [(M+H)+]: 517.2132, found: 517.2133

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; Ding, Qingjie; Jiang, Nan; Liu, Jin-Jun; Ross, Tina Morgan; Zhang, Jing; Zhang, Zhuming; US2010/75948; (2010); A1;,
Ether – Wikipedia,
Ether | (C2H5)2O – PubChem

Adding some certain compound to certain chemical reactions, such as: 437-82-1, name is 2,6-Difluoroanisole, 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 437-82-1. 437-82-1

To a solution of l,3-difluoro-2-methoxy-benzene (3.0 g, 20.8 mmol) in tetrahydrofuran (30 mL) at -70 C was added dropwise n-butyl lithium (1.6 g, 25.0 mmol). The reaction was stirred for 30 mins. Then N,N-dimethylformamide (4.6 g, 63 mmol) was added, and stirring was continued for another 30 minute. The cold bath was removed, and the reaction mixture was stirred at 15 C for 1 hour. On completion, the mixture was extracted with ethyl acetate (2 x 15 mL). The aqueous phase was acidified with 4 M hydrochloric acid and extracted with ethyl acetate (3 x 10 mL). The organic phases were combined, dried over sodium sulfate and evaporated in vacuo to give compound B-256 (3.0 g, 84% yield) as a light yellow liquid. LCMS (B): tR=0.624 min., 173.1 m/z (M+l).

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 2,6-Difluoroanisole.

Reference:
Patent; FORUM PHARMACEUTICALS, INC.; ACHARYA, Raksha; BURNETT, Duane, A.; BURSAVICH, Matthew, Gregory; COOK, Andrew, Simon; HARRISON, Bryce, Alden; KOENIG, Gerhard; MCRINER, Andrew, J.; (400 pag.)WO2016/100184; (2016); A1;,
Ether – Wikipedia,
Ether | (C2H5)2O – PubChem

A common compound: 19056-40-7, name is 4-Bromo-3-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. 19056-40-7

POCl3 (5.07 mL, 54.4 mmol) was added to a mixture of 4-bromo-3- methoxyaniline (10 g, 49.5 mmol) and malonic acid (5.15 g, 49.5 mmol) with thorough mixing, and the mixture was then heated to 105¡ãC. After 5 minutes, the reaction began to bubble vigorously, and eventually formed a hard foam; heating was continued for 1 hour. After cooling, water (200 mL) was added, and the mixture was stirred for 30 minutes. The solid was filtered off and washed with water. 2N NaOH (300 mL) was added to the solid, and stirring was continued overnight. The remaining solid was filtered off; EtOH (5 mL) was then added to the filtrate; and the basic layer was then acidified with concentrated HCl to pH 2. The resulting solid was then filtered off, washed with water. The solid was then transferred to a flask, and the remaining water was removed by stripping off EtOH (200 mL x 2). The solid was then further dried under high vacuum for 15 hours to yield 8.75 g (66percent) of the title compound as an off- white solid. LRMS ESI+ (M+H)+ 270.2/272.2.

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, 19056-40-7, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; MERCK & CO., INC.; WO2008/51514; (2008); A2;,
Ether – Wikipedia,
Ether | (C2H5)2O – PubChem

111-95-5, Adding a certain compound to certain chemical reactions, such as: 111-95-5, name is Bis(2-methoxyethyl)amine, belongs to ethers-buliding-blocks compound, 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 111-95-5.

To the product from step 2 (1.00 g, 5.29 mmol) in ACN (20 mL) was added bis(2- methoxyethyl)amine (3.0 mL, 2.71 g, 20.3 mmol) and the reaction mixture was heated to 70 0C for 16 hours thereafter. The reaction was cooled and concentrated. The residue was partitioned with EtOAc and water. The organic layer was separated and the aqueous was extracted again with EtOAc. The combined organic extracts were washed with brine, dried (Na2SO4), filtered and concentrated. Purification by flash column chromatography (SiO2, 10/1 hexanes-EtOAc to 1/1) afforded 950 mg (63% yield) of the desired adduct as a yellow solid: 1NMR (300 MHz, CDCI3) .delta 7.47 (bs, 2 H), 3.77 (t, J = 5.7 Hz, 4 H)1 3.52 (t, J = 5.4 Hz, 4 H), 3.25 (s, 6 H). 13C NMR (75 MHz, CDCI3) delta 154.7 (s), 152.0 (s), 120.9 (s), 1 19.5 (s), 95.8 (s), 71.0 (t), 59.1 (q), 50.0 (t). LCMS (50-95% gradient acetonitrile in 0.1 % TFA over 10 min), single peak retention time = 4.91 min on 250 mm column, (M+H)+ = 286, (M+Na)+ = 308, (M+Na+ACN)+ = 349.

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, Bis(2-methoxyethyl)amine, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; MALLINCKRODT INC.; WO2007/149479; (2007); A1;,
Ether – Wikipedia,
Ether | (C2H5)2O – PubChem