Month: November 2020

22236-10-8, 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. 22236-10-8, name is 4-(Difluoromethoxy)aniline, This compound has unique chemical properties. The synthetic route is as follows.

General procedure: Method 2: In order to increase the reaction ratio ofexo isomer a solution of methyl 4-formyl-3-methylbenzoate6 (5.61 mmol, 1 g) in anhydrous ACN(60 mL), p-toluidine (5.1 mmol, 547 mg), 3,4-dihydro-2H-pyran (10.2 mmol, 0.93 mL) and TFA(1.12 mmol, 0.087mL) were added. The reactionmixture was stirred 16 h at RT. Solvent was evaporatedand purification of the crude material (60:40 mixtureof exo/endo diastereomers) by flash chromatographyover silica gel using an elution of 15% ethyl acetate inhexanes afforded 1 g (Yield 50%) of the title exoisomer(exo-1c) and 290 mg (Yield 14%) of the titleendo-isomer (endo-1c).

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; Nino, Patricia; Caba, Marta; Aguilar, Nuria; Terricabras, Emma; Albericio, Fernando; Fernandez, Joan-Carles; Indian Journal of Chemistry – Section B Organic and Medicinal Chemistry; vol. 55B; 11; (2016); p. 1384 – 1399;,
Ether – Wikipedia,
Ether | (C2H5)2O – PubChem

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. 5961-59-1, name is 4-Methoxy-N-methylaniline, A new synthetic method of this compound is introduced below., 5961-59-1

General procedure: A 25 mL oven-dried Schlenk tube was sequentially added N-methylaniline 1 or aniline 4 (0.2 mmol), Ethyl Bromodifluoroacetate 2a (81.2 mg, 0.4 mmol), DMF (1ml) and H2O (1 mL) was added under air. The reaction mixture was stirred for 6 h at 110. The solution was then diluted with ethyl acetate (20 mL), washed with brine (10 mL), extracted with ethyl acetate (3*5 mL), dried over anhydrous Na2SO4, filtered and evaporated under vacuum. The crude reaction mixture was purified by column chromatography (silica gel, ethyl acetate/petroleum ether) yielded the desired product 3 or 5.

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; Xu, Zhuo-Wei; Xu, Wen-Yi; Pei, Xiao-Jun; Tang, Fei; Feng, Yi-Si; Tetrahedron Letters; (2019);,
Ether – Wikipedia,
Ether | (C2H5)2O – PubChem

A common heterocyclic compound, 583-19-7, name is 1-Bromo-2-ethoxybenzene, 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. 583-19-7.

Reference Example 160 In THF (120 ml) was dissolved 1-bromo-2-ethoxybenzene (12.0 g). To the mixture was added dropwise at -78 C. 1.6M n-butyllithium/hexane (41.1 ml), and the mixture was stirred for 1 hour. To the mixture was added dropwise a solution of trimethylborate (12.4 g) in THF (12.4 ml), and the mixture was stirred for 30 minutes and warmed to room temperature. To the mixture was added 2N hydrochloric acid (48 ml), and the mixture was stirred for 15 minutes. The reaction mixture was extracted with ethyl acetate, washed with saturated brine and dried with magnesium sulfate. Under reduced pressure, the solvent was evaporated, and the residue was washed with hexane/isopropylether to give 2-ethoxyphenyl borate (7.1 g). 1H-NMR (200 MHz, DMSO-d6) delta 1.37 (3H, t, J=7.0 Hz), 4.09 (2H, q, J=7.0 Hz), 6.89-6.99 (1H, m), 7.33-7.42 (1H, dd, J=7.2, 1.6 Hz), 7.66 (2H, s).

The synthetic route of 1-Bromo-2-ethoxybenzene has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Takeda Chemical Industries, Ltd.; US6235771; (2001); B1;,
Ether – Wikipedia,
Ether | (C2H5)2O – PubChem

Adding some certain compound to certain chemical reactions, such as: 321-28-8, name is 1-Fluoro-2-methoxybenzene, 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 321-28-8. 321-28-8

Step 1. Preparation of 3′-fluoro-4′-methoxyacetophenone Aluminum chloride (80.0 g, 0.6 mol) and chloroform (750 mL) were placed in a 2 L three-necked round bottom flask fitted with a mechanical stirrer and cooled by means of an ice bath. To the stirred solution was added acetyl chloride (51.0 g, 0.65 mol) dropwise, maintaining the temperature between 5-10 C. The mixture was allowed to stir for 10 minutes. at 5 C. before the dropwise addition at 5-10 C. of 2-fluoroanisole (63.06 g, 0.5 mol). The mixture was stirred at 0-10 C. for 1 hour and poured into ice (1 L). The resultant layers were separated and the aqueous layer was extracted with methylene chloride (2*250 mL). The combined organic layers were washed with water (2*150 mL), dried over magnesium sulfate, and concentrated to 300 mL. Hexanes were added and a white solid (77.2 g, 92%) was crystallized from the mixture: mp 92-94 C.; 1 H NMR (d6 -DMSO) 7.8 (m, 2H), 7.3 (t, J=8.7 Hz, 1H), 3.9 (s, 3H), 2.5 (s, 3H).

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 1-Fluoro-2-methoxybenzene.

Reference:
Patent; G.D. Searle & Co.; US5756529; (1998); A;,
Ether – Wikipedia,
Ether | (C2H5)2O – PubChem

104197-14-0, Adding some certain compound to certain chemical reactions, such as: 104197-14-0, name is 4-Bromo-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 104197-14-0.

A mixture of 4-bromo-2,6-difluorophenyl methyl ether (5.Og), 1 ,1-dimethylethyl 1- piperazinecarboxylate (5.Og), 2-biphenylyl[bis(1 ,1-dimethylethyl)]phosphane (0.666g), palladium acetate (0.246g), sodium tert-butoxide (3.01 g) in toluene(30ml) was heated at 9O0C for 16 hours. After cooling ,The reaction mixture was diluted with diethyl ether, filtered through a pad of celite. Then concentrated in vacuo to give a black oil. The desired product was isolated by column chromatography on silica eluting with a gradient of 5 to 100% ethyl acetate in pentane. The title compound was obtained as a solid, (90% yield), LC/MS (ESI) Found 229 (M-BOC+1 ).

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 104197-14-0.

Reference:
Patent; GLAXO GROUP LIMITED; WO2006/94842; (2006); A1;,
Ether – Wikipedia,
Ether | (C2H5)2O – PubChem

52189-63-6, These common heterocyclic compound, 52189-63-6, name is 1-Fluoro-3,5-dimethoxybenzene, 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 suspension of aluminum chloride (8.6 g, 64.04 mmol) in toluene (30 mL) was added 1-fluoro-3,5-dimethoxybenzene (301-3) (10.0 g, 64.04 mmol) at 0 C. The reaction mixture was stirred for 2 hours. To the above mixture was added acetyl chloride (5.0 g, 64.04 mmol). The resulting mixture was stirred for an additional 0.5 hours. The reaction mixture was quenched with water and extracted with ethyl acetate. The organic layer was washed with water and brine, dried over anhydrous sodium sulfate and evaporated in vacuo. The crude product was purified by column chromatography (hexanes/ethyl acetate: 25/1) to afford the title compound 302-3 as a white solid (2.78 g, 22 % yield). ?H NIVIR (400 1VIHz, CDC13): 2.46 (s, 3H), 3.79 (s, 6H), 6.29 (d, J 10.8 Hz, 2H).

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 52189-63-6.

Reference:
Patent; PHARMAENGINE, INC.; CAI, Xiong; QIAN, Changgeng; WANG, Yanong Daniel; (98 pag.)WO2017/132928; (2017); A1;,
Ether – Wikipedia,
Ether | (C2H5)2O – PubChem

Some common heterocyclic compound, 402-52-8, name is 1-Methoxy-4-(trifluoromethyl)benzene, molecular formula is C8H7F3O, 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. 402-52-8

Example 11 B: 2′-methoxy-5′-trifluoromethyl-acetophenone was prepared as follow {US2003/0109574): in a water bath at room temperature, to a solution of trifluoromethane sulfonic acid (5 ml, 56.7 mmol) under argon was slowly added a solution of 4-trifiuoromethyl-anisol (2.0 g, 1 1.35 mmol) in acetic anhydride (2.15 ml, 22.7 mmol). The resulting dark mixture was stirred for 3 hours at room temperature then poured onto ice water (26 ml). The product was extracted several times with ether. The ethereal layer was washed with a 10% solution of sodium hydrogenocarbonate, water, dried over sodium sulfate and concentrated to dryness. The residue was purified by flash chromatography ove . silica gel (gradient cydohexane/dichloromethane: 0-50%) to yield 2′-methoxy-5′-trifluoromethyi- acetophenone (1.7 g, 67%) as a white solid.1 H NMR : CDCI3 delta (ppm): 8.00 (d, J = 2.3 Hz, 1 H), 7.71 (dd, J = 8.8 Hz, J = 2.3 Hz, 1 H), 7.05 (d, J = 8.7 Hz, 1 H), 3.98 (s, 3H), 2.63 (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 402-52-8, its application will become more common.

Reference:
Patent; DOMAIN THERAPEUTICS; PRESTWICK CHEMICAL, INC.; SCHANN, Stephan; MAYER, Stanislas; MORICE, Christophe; GIETHLEN, Bruno; WO2011/51478; (2011); A1;,
Ether – Wikipedia,
Ether | (C2H5)2O – PubChem

54149-17-6, 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. 54149-17-6, name is 1-Bromo-2-(2-methoxyethoxy)ethane belongs to ethers-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below.

To a dimethylsalenium suspension (130 mL) of 2,7-dibromo (6.48 g, 20 mmol) (manufactured by Tokyo Chemical Industry Co., Ltd.), potassium hydroxide (5.61 g, 100 mmol) (0.33 g, 2 mmol) and 1-bromo-2- (2-methoxyethoxy) ethane (8.05 g, 44 mmol) and stirred at room temperature for 24 hours. After completion of the reaction, the mixture was cooled to 0 C, and water (120 mL) was added thereto, followed by neutralization with hydrochloric acid. The organic layer was extracted with ethyl acetate and dried over magnesium sulfate. The crude product was concentrated and purified by silica gel column chromatography (eluent: eluent / ethyl acetate (4/1 – & gt; 3/1)) to give Compound 1 (yield 8.47 g, yield: yellow liquid)80%).

The synthetic route of 1-Bromo-2-(2-methoxyethoxy)ethane has been constantly updated, and we look forward to future research findings.

Reference:
Patent; NISSAN CHEMICAL INDUSTRIES, LTD.; OTA, HIROFUMI; ENDO, TOSHIYUKI; (63 pag.)TW2016/2059; (2016); A;,
Ether – Wikipedia,
Ether | (C2H5)2O – PubChem

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. 494-99-5, name is 1,2-Dimethoxy-4-methylbenzene, A new synthetic method of this compound is introduced below., 494-99-5

Then, 0.6 mol of the thus-obtained compound (VI-2) was dissolved in a 3.5-fold amount by weight, based on (VI-2), of carbon tetrachloride, and 0.66 mol of bromine gas was blown thereinto under reflux condition while irradiating with a mercury vapor lamp. The blowing was completed in 16 hours. After completion of the reaction, the solvent was distilled off to obtain 3,4-dimethoxybenzyl bromide (VII-2) in 92% yield.

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; Sumitomo Chemical Company, Limited; US4335263; (1982); A;,
Ether – Wikipedia,
Ether | (C2H5)2O – PubChem

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 total of 1.64 ml of diisopropylamine was dissolved in 27 ml of tetrahydrofuran, 6.8 ml of a 1.57 M solution of n-butyllithium in hexane was added at -50C under stirring, and the mixture was stirred at -30C for 30 minutes. After cooling to -60C, 2 g of 1-bromo-4-fluoro-2-methoxy-benzene obtained in Production Example II-1-a was added and the mixture was stirred at -60C for 1 hour. Then, 1.55 ml of 3-fluoro-benzaldehyde was added, followed by stirring for 1 hour. Saturated aqueous ammonium chloride solution was added to the reaction mixture, and the mixture was extracted with diethyl ether. The resulting organic layer was washed with brine, dried over magnesium sulfate and the solvent was evaporated, to give 2.4 g of the title compound as a yellow-brown oil.1H-NMR ( 400 MHz, CDCl3 ) d 3.52 ( 3H, s ), 3.56 ( 1H, d, J = 10.4 Hz ), 6.16 ( 1H, d, J=11.6Hz ), 6.86 ( 1H, t, J = 8.8 Hz ), 6.92 – 6.99 ( 1H, m ), 7.07 – 7.16 ( 2H, m ), 7.30 ( 1H, td, J = 8.0, 6.0 Hz ), 7.51 ( 1H, dd, J = 8.8, 6.0 Hz )

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 450-88-4.

Reference:
Patent; Eisai Co., Ltd.; EP1380576; (2004); A1;,
Ether – Wikipedia,
Ether | (C2H5)2O – PubChem