Category: ethers-buliding-blocks

19056-40-7, The chemical industry reduces the impact on the environment during synthesis 19056-40-7, name is 4-Bromo-3-methoxyaniline, I believe this compound will play a more active role in future production and life.

To a stirred solution of 4-bromo-3-methoxyaniline (0.5 g, 2.47 mmol) in toluene (5 mL) were added ethylacetoacetate (0.5 mL, 3.71), sodium ethoxide (0.34 g, 4.94 mmol), and heated to110¡ãC for 16 h. After completion of the reaction, the reaction mixture was diluted with EtOAC(100 mL), washed with water (100 mL), brine (100 mL), dried over sodium sulphate andconcentrated. The residue was purified by colunm chromatography by using silica gel (60-120mesh) to afford the title product as yellow solid (0.4 g, 90percent). 1H NMR (400 MHz, DMSO-d6): oe10.21 (s, 1H), 7.48?7.43 (m, 2H), 7.11?7.08 (m, 1H), 3.83 (s, 3H), 3.54 (s, 2H), 2.20 (s, 3H); ES-MS: mlz 286.1 (M-i-1).

The chemical industry reduces the impact on the environment during synthesis 4-Bromo-3-methoxyaniline. I believe this compound will play a more active role in future production and life.

Reference:
Patent; AURIGENE DISCOVERY TECHNOLOGIES LIMITED; SAMAJDAR, Susanta; ABBINENI, Chandrasekhar; SASMAL, Sanjita; HOSAHALLI, Subramanya; WO2015/104653; (2015); A1;,
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588-96-5, A common heterocyclic compound, 588-96-5, name is p-Bromophenetole, molecular formula is C8H9BrO, 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.

General procedure: b.Cyanation of aryl bromides. To a solution of arylbromide (0.5 mmol) in EtOH (5.0 mL) was added NCTS (272 mg, 1.0 mmol), PdCl2 (13.3 mg, 0.075 mmol), and Ag2O (57.75 mg, 0.5 mmol). The mixture was stirred at 70 for 24 hunder air atmosphere. Then the reaction mixture was cooled to room temperature and filtered through a pad of celite (1.0 g) and rinsed with CH2Cl2 (10.0 mL). The resulting organic solution was concentrated under reduced pressure and further purified by flash chromatography (SiO2,petroleum ether/EtOAc gradient), yielding the corresponding aryl nitriles.

The synthetic route of p-Bromophenetole has been constantly updated, and we look forward to future research findings.

Reference:
Article; Li, Jizhen; Xu, Wenbin; Ding, Junshuai; Lee, Kuo-Hsiung; Tetrahedron Letters; vol. 57; 11; (2016); p. 1205 – 1209;,
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366-99-4, 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. 366-99-4, name is 3-Fluoro-4-methoxyaniline belongs to ethers-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below.

Example 55 Synthesis of N2-cycloheptyl-N4-(2-dimethylamino-ethyl)-N6-(3-fluoro-4-methoxy-phenyl)-1,3,5-triazine-2,4,6-triamine (150) Cyanuric chloride (1.84 g, 10 mmol) in CH3CN (20 mL) was cooled to about -10¡ã C. was added 3-fluoro-p-anisidine (1.41 g, 10 mmol) followed by DIEA (1.8 mL, 10 mmol). The reaction was stirred for about 45 min then at room temperature for about 45 min under an N2 atmosphere. Cycloheptylamine (1.26 mL, 10 mmol) was added followed by DIEA (1.8 mL, 10 mmol) and the reaction was stirred at room temperature overnight. N,N-dimethylethylenediamine (1.1 mL, 10 mmol) was added followed by DIEA (1.8 mL, 10 mmol) and the mixture was heated at reflux under N2 overnight. The reaction was diluted with ethyl acetate, washed with brine, and dried over anhydrous K2CO3. The material (1.178 g) was purified by silica gel column chromatography to afford a solid 150 (1.178 g, 28percent), mp 73-76¡ã C.; HPLC: Inertsil ODS-3V C18, 40:30:30 [KH2PO4 (0.01M, pH 3.2): CH3OH: CH3CN], 264 nm, Rt 10.8 min, 95.1percent purity; MS (ESI): m/z 418 (M+H, 100), 373 (11.9), 322 (7.8), 277 (6.8), 162 (3.6).

The synthetic route of 3-Fluoro-4-methoxyaniline has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Timmer, Richard T.; Alexander, Christopher W.; Pillarisetti, Sivaram; Saxena, Uday; Yeleswarapu, Koteswar Rao; Pal, Manojit; Reddy, Jangalgar Tirupathy; Krlshna Reddy, Velagala Venkata Rama Murali; Sridevi, Bhatlapenumarthy Sesha; Kumar, Potlapally Rajender; Reddy, Gaddam Om; US2004/209880; (2004); A1;,
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24332-20-5, The chemical industry reduces the impact on the environment during synthesis 24332-20-5, name is 1,1,2-Trimethoxyethane, I believe this compound will play a more active role in future production and life.

Example 10 A flask was charged with methoxyacetaldehyde dimethylacetal (1.2 equiv.), trifiuoroacetic acid (1.3 equiv.), and water (equal volume to TFA), and the mixture was stirred at 50 C for 10 min. The reaction mixture was then removed from the heating bath and TEA (1.3 equiv.) was added followed by a solution of 3-(N-Boc-aminomethyl)-azetidine (1 equiv.) in EtOH and DCM, and then NaBH(OAc)3 (3 equiv.). The reaction was stirred for 12 hrs at 20 C. The reaction mixture was extracted and distilled to remove some ethanol. To the organic layer was added 5M HC1 in iPrOH (7 equiv.) at 50 C. TBME was added at 48 C over 45 min, and cooled to 20 C over 60 min. The reaction stirred for another 60 min, filtered, and the filter cake was washed with TBME. The organic layer was dried to provide l-(2-methoxyethyl)-3- (methylamino)-azetidine dihydrochloride.

The chemical industry reduces the impact on the environment during synthesis 1,1,2-Trimethoxyethane. I believe this compound will play a more active role in future production and life.

Reference:
Patent; SATORI PHARMACEUTICALS, INC.; BRONK, Brian, Scott; AUSTIN, Wesley, Francis; CREASER, Steffen, Phillip; FULLER, Nathan, Oliver; HUBBS, Jed, Lee; IVES, Jeffrey, Lee; SHEN, Ruichao; WO2013/36669; (2013); A1;,
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Adding a certain compound to certain chemical reactions, such as: 456-49-5, name is 1-Fluoro-3-methoxybenzene, 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 456-49-5, 456-49-5

EXAMPLE 3 A solution of butyllithium in hexanes (2.5 M; 15.9 ml) was added to a stirring solution of 3-fluoroanisole (5.0 g) in dry tetrahydrofuran (100 ml) at -78 C. and the mixture stirred at that temperature for 30 min. Dry dimethylformamide (3.1 ml) was added and the mixture stirred and allowed to warm to ambient temperature during one hour. Water (150 ml) was added and the mixture extracted with ethyl acetate (3*100 ml). The combined extracts were washed with brine (100 ml), dried over magnesium sulphate, and the solvent removed in vacuo. Distillation of the residue under reduced pressure gave 2-fluoro-6-methoxybenzaldehyde (4.6 g) as an oil b.p. 120 C. at 10.66 mbar.

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, 1-Fluoro-3-methoxybenzene, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; Knoll Aktiengesellschaft; US5935973; (1999); A;,
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398-62-9, name is 4-Fluoro-1,2-dimethoxybenzene, 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. 398-62-9

EXAMPLE 138 6-Bromo-1-(2-fluoro-4,5-dimethoxyphenyl)-1-hexanone A solution of 5.3 g (0.034 mol) of 1,2-dimethoxy-4-fluorobenzene in 25 mL of methylene chloride was added to a solution of 5.4 g (0.041 mol) of aluminum chloride and 8.7 g (0.041 mol) of 6-bromohexanoyl chloride in 60 mL of methylene chloride cooled in an ice bath. The resulting solution was kept at 0 for 5 hours and then worked up as in Example 131. The crude product was recrystallized from methylene chloride-ether to give 6.98 g (62% yield), mp 81-83, of 6-bromo-1-(2-fluoro-4,5-dimethoxyphenyl)-1-hexanone. The nmr spectrum was consistent with the structure and the mass spectrum gave a molecular ion at m/z 332 (C14 H18 BrFO3).

Statistics shows that 398-62-9 is playing an increasingly important role. we look forward to future research findings about 4-Fluoro-1,2-dimethoxybenzene.

Reference:
Patent; Hoffmann-La Roche Inc.; US5025036; (1991); A;,
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111-95-5, 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. 111-95-5 name is Bis(2-methoxyethyl)amine, 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.

General procedure: An oven-dried 20 mL pressurevial was charged with monoester No.13a-f (1.0 eq) and dissolved in anhydrous DMF (0.5 mL/0.1mmol of the monoester). The corresponding amine (1.2 eq) was added, followed by HBTU (1.0 eq).The resulting solution was stirred at 0 C for 5 min, then TEA (2.0 eq) was added and stirring at 0 Cwas continued for 0.5 h. The resulting mixture was warmed to room temperature and stirring wascontinued for 2 h. The brownish solution was diluted with water (20 mL) and extracted with EtOAc(3 x 15 mL). Combined organic extracts were washed with water (15 mL), brine (15 mL), dried overanhydrous Na2SO4 and evaporated under reduced pressure. The residue was purified by silica gelcolumn chromatography.

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

Reference:
Article; Zogota, Rimants; Kinena, Linda; Withers-Martinez, Chrislaine; Blackman, Michael J.; Bobrovs, Raitis; Pantelejevs, Teodors; Kanepe-Lapsa, Iveta; Ozola, Vita; Jaudzems, Kristaps; Suna, Edgars; Jirgensons, Aigars; European Journal of Medicinal Chemistry; vol. 163; (2019); p. 344 – 352;,
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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. 1535-75-7, name is 2-(Trifluoromethoxy)aniline, This compound has unique chemical properties. The synthetic route is as follows., 1535-75-7

To a solution of 2-(trifluoromethoxy)aniline (318A) (2.655 mg, 15 mmol) in acetic acid (6 mL) was added NBS (2.94 g, 16.5 mmol) at 0 C and stirred at room temperature overnight. It was concentrated under reduced pressure. The residue was diluted with ethyl acetate (100 mL), washed with water (30 mL) and brine (30 mL), dried over anhydrous sodium sulfate, concentrated, and purified with flash column chromatography on silica gel (ethyl acetate in petroleum ether, 20% v/v) to afford Compound 318B. LC-MS (ESI) m/z: 256 [M +H]+; ‘H-NMR (CDCb, 400 MHz): d (ppm) 3.89 (s, 2H), 6.67 (d, J= 8.8 Hz, 1H), 7.18 (dd, J= 8.8, 2.4 Hz, 1H), 7.28 (d, J= 2.4 Hz, 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; BIOMARIN PHARMACEUTICAL INC.; WANG, Bing; CHAO, Qi; (737 pag.)WO2019/133770; (2019); A2;,
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Adding some certain compound to certain chemical reactions, such as: 2752-17-2, name is 2,2′-Oxydiethanamine, 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 2752-17-2. 2752-17-2

Cyanuric chloride (2.05 g, 11 mmol, 2 eq)Was dissolved in acetonitrile (25 mL)Cooled to 0 C, 2,2′-oxybis (ethylamine) (0.56 mL, 5.4 mmol, 1 eq)And NaHCO3 (1.83 g, 22 mmol, 4 eq)Followed by addition of the above solution,0 reaction 2h,The reaction is completed.Vacuum steaming solvent,Dissolved in CH2Cl2,Filter out insoluble matter,The filtrate was dried over anhydrous magnesium sulfate,The solvent is evaporated,To give the compound 2,2′-oxobis (ethylamine) -4,4 ‘, 6,6′-tetrachloro-1,1’, 3,3 ‘, 5,5′-briquine (ECl2).

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 2,2’-Oxydiethanamine.

Reference:
Patent; University of Science and Technology of China; Ma Mingming; Zhang Ning; Yan Ziqiang; (32 pag.)CN107235925; (2017); A;,
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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. 767-91-9, name is 2′-Methoxyphenyl acetylene belongs to ethers-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below. 767-91-9

General procedure: To a mixture of alpha-azidoamide 16aa (34 mg, 0.20 mmol) and phenylacetylene (9a; 24 L,0.20 mmol) in t-BuOH/H2O (2 mL, 1:1) were added 0.5 M CuSO4 (0.020 mL, 0.010 mmol) and 1.0 M sodium ascorbate (0.020 mL, 0.020 mmol). The reaction mixture was stirred at room temperature for 1 day, and then the resulting reaction mixture was filtered. The separated solid was washed with H2O and hexanes, and triturated with hexane/EtOAc (10:1) to give the 1-morpholino-2-(4-phenyl-1H-1,2,3-triazol-1-yl)ethanone (2aaa; 52 mg, 96%) as a white solid

The synthetic route of 767-91-9 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Lee, Doohyun; Kim, Daehun; Lee, Seungyeon; Kim, Taegeum; Kim, Joobin; Kim, Sohee; Liu, Kwang-Hyeon; Lee, Sangkyu; Bae, Jong-Sup; Song, Kyung-Sik; Cho, Chang-Woo; Son, Youn Kyung; Baek, Dong Jae; Lee, Taeho; Molecules; vol. 20; 11; (2015); p. 19984 – 20013;,
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