Category: ethers-buliding-blocks

Related Products of 352-67-0, A common heterocyclic compound, 352-67-0, name is 1-Fluoro-4-(trifluoromethoxy)benzene, molecular formula is C7H4F4O, 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.

To a stirred solution [OF TRANS-4-AMINOCYCLOHEXANOL (230] mg, [2MMOL)] in DMF (10 mL) at 0 C was added 60% NaH in mineral oil (240 mg, 6 mmol). The reaction mixture was stirred at 0 [C] [FOR’/2 HOUR] and then [1-FLUORO-4- (TRIFLUOROMETHOXY)] benzene (432 mg, 2.4 mmol) was added. It was heated to 60 [C] for 2 hours and stirred for 12 hours at room temperature. The reaction mixture was diluted with ethyl acetate and washed with water (3 times) and brine. The organic layer was dried (sodium sulfate), filtered, and concentrated under reduced pressure to provide the titled compound. MS (DCI) [M/Z] 276 (M+H) [+.]

The synthetic route of 352-67-0 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; ABBOTT LABORATORIES; WO2004/26822; (2004); A2;,
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Some common heterocyclic compound, 111-95-5, name is Bis(2-methoxyethyl)amine, molecular formula is C6H15NO2, 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. Computed Properties of C6H15NO2

A solution of (S)-isopropyl 2-(6-(bromomethyl)-4-(4,4-dimethylpiperidin-1-yl)-5-(4-(4- fluorophenethoxy)phenyl)-2-methylpyridin-3 -yl)-2-(tert-butoxy)acetate (0.015 g, 0.022 mmol) and bis(2-methoxyethyl)amine (0.02 g, 0.150 mmol) in EtOH (1 mL) was stirred for 2 h. Sodium hydroxide(0.04 g, 1.000 mmol) was added and the reaction mixture wasstirred at 80 C for 2 h. Then, cooled and purified by prep HPLC to afford (S)-2-(6- ((bis(2-methoxyethyl)amino)methyl)-4-(4,4-dimethylpiperidin- 1 -yl)-5-(4-(4- fluorophenethoxy)phenyl)-2-methylpyridin-3 -yl)-2-(tert-butoxy)acetic acid (0.0127 g, 0.0 18 mmol, 83 % yield). LCMS (M+H) = 694.2.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 111-95-5, its application will become more common.

Reference:
Patent; VIIV HEALTHCARE UK (NO.5) LIMITED; EASTMAN, Kyle J.; KADOW, John F.; NAIDU, B. Narasimhulu; PARCELLA, Kyle E.; PATEL, Manoj; SIVAPRAKASAM, Prasanna; TU, Yong; (275 pag.)WO2017/25915; (2017); A1;,
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Synthetic Route of 366-99-4,Some common heterocyclic compound, 366-99-4, name is 3-Fluoro-4-methoxyaniline, molecular formula is C7H8FNO, 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.

Example 62; Synthesis of N,N’-dicyclopropyl-N-(3-fluoro-4-methoxy-phenyl)-1,3,5-triazine-2,4,6-triamine (157); To cyanuric chloride (0.368 g, 2 mmol) in CH3CN at about -20° C. was added 3-fluoro-p-anisidine (0.28 g, 2 mmol) in CH3CN followed by the addition of DIEA (0.39 mL, 2.2 mmol) and stirred for about I hour. The reaction mixture was then stirred at room temperature for about 1 hour. Then cyclopropylamine (1.39 mL, 20 mmol) and DIEA (0.39 mL, 2.2 mmol) were added and the reaction mixture was stirred overnight at rt. The reaction mixture was worked up as usual, diluted with ethyl acetate and washed with brine. The organic layer was separated and dried over sodium sulfate, filtered, concentrated under reduced pressure, and compound 157 was purified by silica gel column chromatography (200 mg, 30percent), mp 91-92° C.; HPLC: Inertsil ODS-3V C18, 40:30:30 [KH2PO4 (0.01 M, pH 3.2):CH3OH:CH3CN], 264 nm, Rt 8.6 min, 99.1percent purity; MS (ESI): m/z 331(M+H, 100), 305 (0.8), 151 (0.3).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 3-Fluoro-4-methoxyaniline, its application will become more common.

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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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. 38603-09-7, name is 1,3-dibromo-2-methoxybenzene belongs to ethers-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below. Quality Control of 1,3-dibromo-2-methoxybenzene

To a THF solution of 2,6-dibromoanisole (10 g, 37.6 mmol) was added Mg (0.90 g, 37.6 mmol), and the mixture was heated and stirred at 40C. Under ice-cooling, n-heptanal (47.2 g, 41.3 mmol) was added dropwise. Aqueous hydrochloric acid solution was added to the reaction mixture, this was extracted with ethyl acetate, and the solvent was distilled off to obtain 8.95 g of a compound (1). NMR (CDCl3) delta ppm: 7.45 – 7.48 (m, 1H), 7.35 – 7.38 (m ,1H), 7.01 (t, 1H, 8.1 Hz), 4.96 – 5.00 (m, 1H), 3.88 (s, 3H), 1.70 – 1.80 (m, 2H), 1.25 – 1.63 (m ,8H), 0.85 – 0.90 (m, 3H)

The synthetic route of 38603-09-7 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Shionogi&Co., Ltd.; EP2184279; (2010); A1;,
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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. 456-55-3, name is (Trifluoromethoxy)benzene, A new synthetic method of this compound is introduced below., HPLC of Formula: C7H5F3O

EXAMPLE 2 4-Trifluoromethoxy-alpha,alpha,alpha-trifluoroacetophenone was prepared from 4-bronotrifluoromethoxybenzene by a procedure similar to that described in Example 1. 4-Bromotrifluoromethoxybenzene may be prepared from trifluoromethoxybenzene by the process described in the Journal of Organic Chemistry, 29, 1, (1964). Boiling point: 164-166 C. (atmosphere pressure). 1 H NMR (CDCl3)delta (ppm): 7.35, 8.14 (4H,d), 19 F NMR (CDCl3)delta (ppm relative to CFCl3): -58.1 (s) CF3 O. -72.1 (s) CF3.

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; Imperial Chemical Industries PLC; US4891450; (1990); A;,
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Electric Literature of 887267-47-2, The chemical industry reduces the impact on the environment during synthesis 887267-47-2, name is 2-Bromo-5-(trifluoromethoxy)aniline, I believe this compound will play a more active role in future production and life.

The aryl halide (e.g., 1.00 mmol), triethylamine (e.g., 2.00 mmol) and P(o-tol)3 (e.g., 0.30 mmol) were dissolved in acetonitrile (e.g., 0.5 M) in a glass pressure tube and nitrogen gas was bubbled through the solution via a gas dispersion tube for 10 minutes. Ethyl acrylate (e.g., 1.25 mmol) and palladium acetate (e.g., 0.10 mmol) were added to the reaction mixture and the tube was sealed and placed into an oil bath pre-heated to about 120 0C for about 18 h. The resulting solution was concentrated under vacuum and purified (e.g., silica gel column).The title compound was prepared from 2-bromo-5-(trifluoromethoxy)aniline according to protocol M. Retention time (min) = 2.693, method [1], MS(ESI) 276.1 (M+Eta).

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-Bromo-5-(trifluoromethoxy)aniline, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; ELAN PHARMACEUTICALS, INC.; SHAM, Hing, L.; KONRADI, Andrei, W.; HOM, Roy, K.; PROBST, Gary, D.; BOWERS, Simeon; TRUONG, Anh; NEITZ, R., Jeffrey; SEALY, Jennifer; TOTH, Gergely; WO2010/91310; (2010); A1;,
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Adding a certain compound to certain chemical reactions, such as: 887267-47-2, name is 2-Bromo-5-(trifluoromethoxy)aniline, 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 887267-47-2, Computed Properties of C7H5BrF3NO

To a solution of 2-bromo-5-(trifluoromethoxy)benzenamine (1.0 g, 3.9 mmol) in 20 mL of tetrahydrofuran were added /V,//-dimethylpyridin-4-amine (50 mg, 0.4 mmol), and di-tert-butyl dicarbonate (2.55 g,11.7 mmol). The resulting mixture was stirred at reflux for overnight. After cooled to room temperature, the solvent was removed in vacuo and the residue was purified by silica gel column chromatography (petroleum ether: ethyl acetate = 10: 1) to give 1.4 g (80%) of the product as a white solid. MS (ESIpos): m/z = 456 (M+H)+; LC-MS [Method 2] : R, = 1.07 min.

At the same time, in my other blogs, there are other synthetic methods of this type of compound, 2-Bromo-5-(trifluoromethoxy)aniline, and friends who are interested can also refer to it.

Reference:
Patent; BAYER AKTIENGESELLSCHAFT; BAYER PHARMA AKTIENGESELLSCHAFT; NGUYEN, Duy; WORTMANN, Lars; FARIA ALVARES DE LEMOS, Adelaide, Clara; BOeMER, Ulf; SUeLZLE, Detlev; HOLTON, Simon; LECHNER, Christian; (147 pag.)WO2019/170543; (2019); 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. 121588-79-2, name is trans-4-Methoxycyclohexanamine, This compound has unique chemical properties. The synthetic route is as follows., Recommanded Product: trans-4-Methoxycyclohexanamine

4.71 g (10 mmol) of compound VII was dissolved in 20 ml of 1,4-dioxane.Add to the solution1.937 g (15 mmol) of trans-4-methoxycyclohexylamine and 0.12 ml of glacial acetic acid,The mixture was heated to reflux for 15 hours, and the reaction mixture was concentrated under reduced pressure, and then evaporated,The solid was dispersed, suction filtered, and the filter cake was washed with 10 ml of ethanol and dried.Crude4.62g,The yield was 78.4%.

According to the analysis of related databases, 121588-79-2, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Beijing Concorde Pharmaceutical Er Factory; Chinese Academy Of Medical Sciences Pharmaceutical Institute; Zhang Dongfeng; Huang Haihong; Li Chun; Yin Dali; Lin Ziyun; Ma Chen; Wang Mijuan; Zhang Meng; Lan Pei; Zhao Limin; (11 pag.)CN109748903; (2019); A;,
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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. 17600-72-5, name is 1-Ethoxy-2-methoxybenzene, This compound has unique chemical properties. The synthetic route is as follows., Application In Synthesis of 1-Ethoxy-2-methoxybenzene

A 2-way cock with a septum at the tip was attached to a recovery flask containing o-ethoxymethoxybenzene (150 mg, 0.98 mmol) and dried by allowing to stand overnight under reduced pressure in the presence of diphosphorus pentoxide, It was returned to atmospheric pressure with nitrogen. After reducing the pressure with a diaphragm pump again, hydrogen iodide gas (127 mg, 0.99 mmol) was introduced from the septum using a 50 mL syringe and returned to atmospheric pressure by filling with nitrogen and then allowed to stand at 25 C. for 48 hours I put it. After the reaction, the mixture was reduced in pressure by a diaphragm pump to obtain a mixture (139.0 mg) of o-ethoxyphenol, o-methoxyphenol and o-ethoxymethoxybenzene. The yield was determined to be 77%: 9%: 14% o-ethoxyphenol: o-methoxyphenol: o-ethoxymethoxybenzene from the integration ratio of 1 H-NMR using phenanthrene as an internal standard.

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 17600-72-5.

Reference:
Patent; Chiba University; Godo Shigen Co., Ltd; Matsumoto, Shoji; Akazome, Motohiro; Otani, Yasuhiko; (14 pag.)JP5725506; (2015); B2;,
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Adding a certain compound to certain chemical reactions, such as: 15799-79-8, name is 3-Methoxy-N,N-dimethylaniline, 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 15799-79-8, Formula: C9H13NO

[0086] (R)-3-(4-Dimethylamino-2-methoxy-phenyl)-butyraldehyde (Table 1, entry 1). To a 2-dram vial equipped with a magnetic stir bar was added (2S,5S)-5-benzyl-2-tert-butyl-3-methylimidazolidin-4-one (12.3 mg, 0.050 mmol, 0.100 equiv), CH2Cl2 (0.50 ml), HCl (as a 4N solution in 1,4-dioxane, 12.5 uL, 0.050 mmol, 0.100 equiv), and N,N-dimethyl-m-anisidine (73.3 uL, 0.500 mmol, 1.00 equiv). The solution was cooled to -40o C. before crotonaldehyde (124 uL, 1.50 mmol, 3.00 equiv) was added. After 36 h, the reaction mixture was subjected directly to silica gel chromatography. Elution with 20% EtOAc in hexanes followed by concentration and removal of residual crotonaldehyde under vacuum afforded the product as a colorless oil in 86% yield (94.9 mg, 0.429 mmol); 89% ee. IR (film) 2958, 2874, 2834, 2719, 1721, 1615, 1568, 1516, 1462, 1441, 1352, 1238, 1133, 1034, 979.6, 814.0 cm-1; 1H NMR (300 MHz, CDCl3) ?9.67 (t, J=2.7 Hz, 1H, CHO), 7.03 (d, J=8.2 Hz, 1H, ArH), 6.31 (dd, J=2.5, 8.2 Hz, 1H, ArH), 6.27 (d, J=2.5 Hz, 1H, ArH), 3.83 (s, 3H, OCH3), 3.63 (dq, J=7.1, 7.1 Hz, 1H, ArCH), 2.94 (s, 6H, N(CH3)2), 2.68 (ddd, J=2.5, 6.9, 15.9 Hz, 1H, CH2CO), 2.55 (ddd, J=2.8, 7.7, 15.9 Hz, 1H, CH2CO), 1.27 (d, 3H, CHCH3); 13C NMR (75 MHz, CDCl3) ?203.7, 157.8, 150.9, 127.5, 121.7, 15.1, 96.6, 55.4, 51.2, 41.0, 27.6, 20.9. HRMS (CI) exact mass calcd for (C13H19NO2) requires m/z 222.1494 for [M+H]+, found m/z 222.1497. [?]D=-9.5 (c=1.0, CHCl3). The enantiomeric ratio of the product was determined by HPLC analysis of the corresponding alcohol (obtained by NaBH4 reduction) using a Chiracel AD and AD guard column (3.0% ethanol/hexanes, 1 mL/min); S isomer tr=21.6 min, R isomer tr=23.1 min.

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; MacMillan, David W.C.; Paras, Nick A.; US2003/236438; (2003); A1;,
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