Month: February 2021

Adding a certain compound to certain chemical reactions, such as: 5961-59-1, name is 4-Methoxy-N-methylaniline, 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 5961-59-1, Recommanded Product: 5961-59-1

[[00146]] To a mixture of N-methyl-p-anisidine (2.8 g, 20 mmol) and malonic acid (4.3 g, 40 mmol) was added POC13 (17 mL). After heating at [90¡ã] C for 1.5 hr, the reaction mixture was poured over ice and basified with 6N [NAOH] to a pH of 14. The solution was then filtered and the filtrate was acidified with, 6N HC1 to pH 3. The precipitate was filtered and dried to afford a brown solid (1.8 g, [50percent). H] NMR (300 MHz, [MEOD-] d4) [8] 3.65 (3H, s), 3.86 (3H, s), 5.97 [(1H,] s), 7.28 [(1H,] dd, J [=] 2.8, 9.3 Hz), 7.49 (2H, d, J = 9.3 Hz).

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

Reference:
Patent; MILLENNIUM PHARMACEUTICALS, INC.; WO2003/106452; (2003); A2;,
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Application of 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.

3-(trifluoromethoxy)aniline (50.0 mg, 0.28 mmol), intermediate E (80.0 mg, 0.24 mmol), DMAP (1.5 mg, 0.01 mmol) and DIEA (62.0 mg, 0.48 mmol) in DMF (5 mL) was heated at 85¡ãC for 10h under N2. Water (10 mL) was added and the mixture was extracted with ethyl acetate (2 x 10 mL). The combined organics were dried over Na2SO4 , filtered and concentrated under reduced pressure. The residue was purified by silica gel column chromatography (eluent: DCM:MeOH = 15:1) to afford the titled compound (40.0 mg, 30percent) as a yellow solid. (0622) LCMS (method B): 2.66 min [MH]+=566.0. 1H NMR (400 MHz, DMSO-d6) delta 9.53 (s, 2H), 9.44-9.41 (m, 2H), 8.10 – 8.09 (m, 1 H),7.80 – 7.78 (m, 2H), 7.64 (dd, J = 8.4, 2.0 Hz, 1 H), 7.32 (br s, 1 H), 7.20 (br s, 1 H), 7.12-7.07 (m, 2H), 6.96 (d, J = 8.4 Hz, 2H), 6.65 (d, J = 8.4 Hz, 2H), 5.70 (d, J= 6.0 Hz, 1 H), 3.43 (s, 3H, covered), 2.74 (d, J = 3.9 Hz, 3H), 2.25 (s, 3H).

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:
Patent; CATALYST THERAPEUTICS PTY LTD; LESSENE, Guillaume Laurent; GARNIER, Jean-Marc; CUZZUPE, Anthony Nicholas; FEUTRILL, John Thomas; CZABOTAR, Peter Edward; SHARMA, Pooja; (142 pag.)WO2016/127213; (2016); A1;,
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Reference of 109-85-3, The chemical industry reduces the impact on the environment during synthesis 109-85-3, name is 2-Methoxyethylamine, I believe this compound will play a more active role in future production and life.

Step 1 2-Chloro-5-nitropyridine (4.0 g) was stirred with 2-methoxyethylamine (20 mL) at room temperature for 1 h. The reaction mixture was diluted with water (30 mL) and extracted with ethyl acetate (2*50 mL), washed with brine (20 mL), dried over sodium sulfate and evaporated under vacuum. The residue was washed with n-pentane (25 mL) to get N-(2-methoxyethyl)-5-nitropyridin-2-amine (4.8 g, 87%) as yellow solid.

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-Methoxyethylamine, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; Gruenenthal GmbH; FRANK, Robert; BAHRENBERG, Gregor; CHRISTOPH, Thomas; LESCH, Bernhard; LEE, Jeewoo; US2013/29962; (2013); A1;,
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Application of 6876-00-2, 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. 6876-00-2, name is 1-Bromo-3-phenoxybenzene, This compound has unique chemical properties. The synthetic route is as follows.

EXAMPLE 18 4-(4-Chlorophenyl)-2-fluoro-4-methyl-1-(3-phenoxyphenyl)pent-2-ene The method of Example 16 was repeated using a Grignard reagent, prepared from 3-phenoxyphenyl bromide (0.19 g), tetrahydrofuran (2 ml) and magnesium (22 g), and 4-(4-chlorophenyl)-2-fluoro-4-methylpent-2-enyl acetate (Example 13) (0.12 g). The residue after evaporation was purified by preparative thin layer chromatography (solvent: diethyl ether/hexane; 1:9) and then preparative high performance liquid chromatography (column: C18; solvent: methanol; flow rate: 3 ml/min; to give the title compound (38 mg, 22%).

The chemical industry reduces the impact on the environment during synthesis 1-Bromo-3-phenoxybenzene. I believe this compound will play a more active role in future production and life.

Reference:
Patent; British Technology Group, Ltd.; US5880162; (1999); A;,
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Adding a certain compound to certain chemical reactions, such as: 67191-35-9, name is 1-Isopropoxy-2-vinylbenzene, 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 67191-35-9, Recommanded Product: 1-Isopropoxy-2-vinylbenzene

Under anhydrous and anaerobic conditions,Grubbs first generation catalyst 1a (1.22mmol)Add to a 100mL Schlenk bottle,Compound IIIaa (2858 mg, 2.43 mmol) andPotassium tert-butoxide (286 mg, 2.55 mmol)Add to the reaction bottle,Add 50 mL of n-hexane.After reacting at 60 C for 5 hours with stirring,TLC monitored the reaction completely.After the reaction was completed, n-hexane was removed under reduced pressure.The intermediate obtained in the previous step was dissolved in 40 mL of dichloromethane.Add cuprous chloride (300 mg, 1.42 mmol) and stir for 5 min.Compound 2a1 (296 mg, 1.82 mmol) was added to the reaction flask and the temperature was raised to 40 C.TLC monitored the reaction completely.After completion of the reaction, column chromatography gave 574 mg of light green solid powder IIaa1, yield: 32.3%.

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

Reference:
Patent; Chengdu Kaimeisi Business Wu Information Advisory Center (Limited Partner); Chen Jianxin; (28 pag.)CN110041262; (2019); A;,
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Related Products of 450-88-4, These common heterocyclic compound, 450-88-4, name is 1-Bromo-4-fluoro-2-methoxybenzene, 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 1 -bromo-4-fluoro-2-methoxybenzene (CAS No. [450-88-4]; 10.0 g, 48.8 mmol) in concentrated sulfuric acid (50 mL) was cooled to 0 C and treated dropwise with a freshly prepared mixture of fuming nitric acid (1.05 eq., 2.1 mL, 51 mmol) and concentrated sulfuric acid (1.85 eq., 4.8 mL, 90 mmol). The reaction mixture was stirred at 0 C for 30 minutes and poured in small portions on ice water. The formed precipitate was filtered off, washed with cold water and kept. The filtrate was extracted with ethyl acetate and the organic layer combined with the isolated precipitate. The organic layer was dried with sodium sulfate and concentrated in vacuo. The obtained material was purified by flash chromatography (Si02-hexane/ ethyl acetate) to give the title compound (5.88 g, 44%).1H-NMR (400MHz, DMSO-de): delta [ppm] = 4.00 (s, 3H), 7.44 (d, 1 H), 8.40 (d, 1 H).UPLC- MS (ESI-): [M – H] = 248/250; R, = 1.17 min (Br isotope pattern; Method E).

The synthetic route of 450-88-4 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; BAYER PHARMA AKTIENGESELLSCHAFT; PANKNIN, Olaf; RING, Sven; ZIMMERMANN, Katja; NEUHAUS, Roland; (153 pag.)WO2017/9325; (2017); 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. 33170-72-8, name is 2-Bromo-1,1-dimethoxypropane belongs to ethers-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below. Product Details of 33170-72-8

Step 1: (1,1-Dimethoxypropan-2-yl)hydrazine 6.25 g (34.1 mmol) of 2-bromo-1,1-dimethoxypropane and 6.65 ml (137 mmol) of hydrazine hydrate were stirred under reflux in an oil bath at 140 C. for 6 h. After cooling, the two-phase reaction mixture was extracted with 50 ml of tert-butyl methyl ether. The organic phase was filtered, the filtrate was concentrated on a rotary evaporator and the residue was dried under high vacuum. This gave 1.89 g (21% of theory) of a pale yellow oil which was reacted directly, without further purification, in the subsequent reaction.

The synthetic route of 33170-72-8 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; BAYER INTELLECTUAL PROPERTY GMBH; SUessMEIER, Frank; LOBELL, Mario; GRUeNEWALD, Sylvia; HAeRTER, Michael; BUCHMANN, Bernd; TELSER, Joachim; JOeRIssEN, Hannah; HEROULT, Melanie; KAHNERT, Antje; LUSTIG, Klemens; LINDNER, Niels; US2013/190290; (2013); A1;,
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Synthetic Route of 74137-36-3, 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. 74137-36-3 name is 1,3-Dibromo-5-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.

A solution of 1,3-dibromo-5-methoxybenzene (24.5 g, 92.13 mmol, 1 equiv) in Et2O (400 mL) under nitrogen, cooled to -78 oC and stirred for 20 min was added n-BuLi (2.5mol/L in THF, 44 mL, 1.20 equiv) dropwised at -78 oC. The reaction mixture was continued to stir for 1h at -78 oC followed by addition of DMF (8.1 g, 110.55 mmol, 1.2 equiv) dropwise. After stirring for 45 min at -78oC, the reaction was quenched with water (200 ml) carefully and extracted with EtOAc (500 mL) twice. The combined organic layers were concentrated under reduced pressure to give a mixture, which was further triturated with hexane (200mL) to afford 3-bromo-5-methoxybenzaldehyde (45-2) (14.5 g, 73.2%) as a white solid.

At the same time, in my other blogs, there are other synthetic methods of this type of compound, 1,3-Dibromo-5-methoxybenzene, and friends who are interested can also refer to it.

Reference:
Patent; CYTOKINETICS, INC.; CHUANG, Chihyuan; MORGAN, Bradley P.; VANDERWAL, Mark; WANG, Wenyue; ASHCRAFT, Luke W.; (362 pag.)WO2019/144041; (2019); A1;,
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Related Products of 33311-29-4, 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. 33311-29-4 name is 4-(2-Methoxyethoxy)aniline, 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.

Example No. 104Preparation of [4- (2-Methoxy-ethoxy) -phenyl] – (8-methoxy-3H- pyrazolo [3 , 4-c] quinolin-4 -yl) -amine4-chloro-8-methoxy-2- (4 -methoxybenzyl) -2H-pyrazolo [3,4- c] quinoline (0.16 mmol) and 4- (2-methoxyethoxy) aniline (2 eq.,0.3 mmol) were suspended in MeOH (dry, 3mL) in a microwave vial (2-5mL) , HCl in dioxane (4M, 3 drops) was added. The reaction mixture was irradiated in a microwave reactor for 5 min at 140C. The reaction mixture was evaporated and used without further purification. The residue was dissolved in TFA (3mL) . The reaction mixture was irradiated in a microwave reactor for 5 min at 140 C. The reaction mixture was concentrated and purified by semi-preparative HPLC-MS and freeze dried from water/t-BuOH 4/1. exact mass: 364.1833 g/molHPLC-MS: analytical method Brt: 1.90 min – found mass: 365.2 (m/z+H)

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

Reference:
Patent; ORIGENIS GMBH; ALMSTETTER, Michael; THORMANN, Michael; TREML, Andreas; KOESTLER, Roland; YEHIA, Nasser; WO2012/143143; (2012); 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. 75148-49-1, name is 3-Bromobenzaldehyde Diethyl Acetal, A new synthetic method of this compound is introduced below., HPLC of Formula: C11H15BrO2

As shown in FIG. 2, 3.3 mmol of 3-bromobenzaldehyde diethanol and 3.8 mmol of nitrile ethyl acetate were mixed and diluted with ethyl acetate to 10 mL, and then the resulting solution was reacted by continuous flow at a flow rate of 1 mL / min. The device was pumped into the first HPLC column (containing 1 g PS-perazine) and the second HPLC column (containing 1 g PS-N-SO3) in sequence, and the first and second HPLC columns were immersed in an oil bath at 50 C. and reacted for 3 hours. After the reaction was completed, the HPLC column was rinsed with ethyl acetate, the product was collected, ethyl acetate was evaporated, and recrystallized from ethanol to obtain a solid product with a yield of 91%.

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; Huaqiao University; Xiong Xingquan; Liao Xu; (11 pag.)CN110818592; (2020); A;,
Ether – Wikipedia,
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