Month: May 2021

Electric Literature of 38603-09-7, These common heterocyclic compound, 38603-09-7, name is 1,3-dibromo-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.

2-(3,5-Dibromo-4-methoxyphenyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane (B) A mixture of 1,3-dibromo-2-methoxybenzene (0.6586 g, 2.48 mmol), bis(pinacolato)diboron (0.4402, 1.73 mmol) and 4,4′-di-tert-butyl-2,2′-dipyridyl (1.3 mg, 0.0048 mmol) in degassed anhydrous THF (2.5 mL) in a reaction tube was purged by bubbling nitrogen through for 5 min. Di-mu-methoxybis(1,5-cyclooctadiene)diiridium(I) (1.6 mg, 0.0024 mmol) was added and the mixture was purged with nitrogen for a few more minutes. The tube was then capped and heated at 80 C. for 19 h. More di-mu-methoxybis(1,5-cyclooctadiene)diiridium(I) (3.4 mg, 0.0051 mmol) and 4,4′-di-tert-butyl-2,2′-dipyridyl (2.9 mg, 0.0108 mmol) was added and the mixture was purged with nitrogen again. The tube was then capped and heated at 80 C. for a further 18 h. The solvent was evaporated and the residue was purified by flash chromatography (silica gel, 5% EtOAc/pet. ether) to afford 0.8575 g (88%) of the title compound as a white solid. 1H NMR delta (ppm)(CDCl3): 1.33 (12H, s), 3.90 (3H, s), 7.92 (2H, s).

Statistics shows that 1,3-dibromo-2-methoxybenzene is playing an increasingly important role. we look forward to future research findings about 38603-09-7.

Reference:
Patent; Institute for OneWorld Health; US2009/270398; (2009); A1;,
Ether – Wikipedia,
Ether | (C2H5)2O – PubChem

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. 50868-72-9, name is 5-Methoxy-2-methylaniline, This compound has unique chemical properties. The synthetic route is as follows., HPLC of Formula: C8H11NO

A solution of 5-methoxy-2-methylbenzenamine (1.3 g, 9.48 mmol) in 48% HBr (13 mL) and EtOH (10 mL) was cooled to 0 C. and NaNO2 (0.78 g, 11.30 mmol) in water (5 mL) was added dropwise over 15 minutes while keeping the temperature of the reaction between 0-5 C. After the clear pale brown solution was kept at 0 C. with stirring for 1 h, this solution was transferred into the boiling solution of CuBr (6.8 g, 47.4 mmol) in 48% HBr (25 mL). The solution was refluxed for overnight. The reaction mixture was cooled to room temperature and the reaction was diluted with water (50 mL). The acidic solution was extracted with ethyl acetate (2*50 mL). The combined ethyl acetate was washed by saturated NaCl (1*50 mL) and was dried over sodium sulfate. The sodium sulfate was removed by filtration and the solvent was removed by vacuum. The crude product was purified by silica gel column (3.5*16 cm) chromatography with hexanes as an eluent to yield colorless oil (750 mg, 39%).

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 50868-72-9.

Reference:
Patent; TargeGen, Inc.; US2005/245524; (2005); A1;,
Ether – Wikipedia,
Ether | (C2H5)2O – PubChem

Synthetic Route of 887267-47-2, These common heterocyclic compound, 887267-47-2, name is 2-Bromo-5-(trifluoromethoxy)aniline, 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: 1,1-Cyclopropanedicarboxylic acid (5) (12.0 g, 15.4 mmol) was dissolved in anhydrous THF (50 mL). Then triethanolamine (2.0 mL,13.9 mmol) was added to the mixture and the mixture was stirred on the ice-bath for 30 min. SOCl2 (1.2 mL, 16.66 mmol) was then added. Stirring was continued for 2h, a solution of 3,5-dimethylaniline 6 (3.6 g, 15.4 mmol) in anhydrous THF (10 mL) was added and continued stirring for 2h, after that, the ice bath was removed, and the mixture was stirred at room temperature overnight. After the completion of the reaction, the mixture was filtered and concentrated in vacuo. The residues was purified by silica gel flash chromatography (PE/AcOEt = 5:1) to yield 7 as white solid (0.8 g, 30.7%).

Statistics shows that 2-Bromo-5-(trifluoromethoxy)aniline is playing an increasingly important role. we look forward to future research findings about 887267-47-2.

Reference:
Article; Li, Chuansheng; Shan, Yuanyuan; Sun, Ying; Si, Ru; Liang, Liyuan; Pan, Xiaoyan; Wang, Binghe; Zhang, Jie; European Journal of Medicinal Chemistry; vol. 141; (2017); p. 506 – 518;,
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Reference of 2186-92-7, 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. 2186-92-7, name is P-anisaldehyde dimethyl acetal belongs to ethers-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below.

General procedure: To a stirred benzaldehyde dimethyl acetal 1a solution of (15 mmol) was added a freshly prepared MgI2 etherate (1.5 mmol, 1.0M in Et2O/PhMe) at room temperature, followed by addition of trimethylsilyl cyanide (18 mmol). The resulting reaction mixture was stirred at room temperature for 3.0 h. chromatographic purification of the crude producton silica gel gave the 2-phenyl-2-methoxyacetonitrile 2a in 95% yield.

The synthetic route of P-anisaldehyde dimethyl acetal has been constantly updated, and we look forward to future research findings.

Reference:
Article; Li, Hua; Pan, Haokun; Meng, Xiangwei; Zhang, Xingxian; Synthetic Communications; vol. 50; 5; (2020); p. 684 – 691;,
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Electric Literature of 4457-67-4, These common heterocyclic compound, 4457-67-4, name is 1-Bromo-4-methoxybutane, 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.

(2) Production of 4′-methoxybutyloxybiphenyl-4-carboxylic acid 7.2 Grams of 1-bromo-4-methoxybutane and 4.5 g of 4′-hydroxybiphenyl-4-carboxylic acid were refluxed in 100 ml of water and 400 ml of ethanol for 4 hours. Concentrated hydrochloric acid was added to the reaction mixture so that the mixture showed pH 1, then 150 ml of water was added, and the resultant mixture was refluxed for 1 hour. The reaction mixture was cooled to precipitate a crystal, and the crystal was recovered by filtration. The so-obtained crystal was recrystallized from acetone. Yield 61percent.

Statistics shows that 1-Bromo-4-methoxybutane is playing an increasingly important role. we look forward to future research findings about 4457-67-4.

Reference:
Patent; Mitsubishi Gas Chemical Company, Inc.; US5340498; (1994); 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. 2050-47-7, name is 4,4′-Oxybis(bromobenzene), A new synthetic method of this compound is introduced below., Application In Synthesis of 4,4′-Oxybis(bromobenzene)

Bis- (4-bromophenyl) ether (30 g, 0.092 mol), a, a, a-trichlorotoluene (22 ml, 0. 15 mol), aluminum chloride (20 g, 0.15 mol) in dichloromethane (75 ml) were stirred at room temperature for 1 hour. The reaction mixture was poured into water (100 ml) and hexane (300 ml and the suspension was stirred overnight. The mixture was then filtered, washed with water (230 ml) and hexane 400 ml) and dried to give the title compound as a crystalline solid (34.94 g, yield: 88%).

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; ISIS PHARMACEUTICALS, INC.; WO2005/77966; (2005); A1;,
Ether – Wikipedia,
Ether | (C2H5)2O – PubChem

Electric Literature of 40515-89-7, 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. 40515-89-7, name is Phenethoxybenzene, This compound has unique chemical properties. The synthetic route is as follows.

General procedure: Lignin model molecule (2-phenoxy-1-phenylethanol) wassynthesized according to the method reported by Rothenberg[9]. Catalytic hydrotreating of 2-phenoxy-1-phenylethanolwas carried out in a 100ml autoclave with Tefon liner.The catalyst (50mg) was added to a solution of 2-phenoxy-1-phenylethanol (150mg) in ethanol (2ml) and H2O(8ml).The autoclave was sealed and purged with H2several times.The reaction was performed at 170C with 2MPa hydrogenpressure for 6h. Then, the reactors were cooled down toroom temperature using an ice bath, and the organic productswere extracted with ethyl acetate (5ml × 2). The organic products mixtures were analyzed by GC and chlorobenzenewas used as an external standard. Identification of mainproducts was based on GC-MS as well as by comparisonwith authentic samples. The product distribution was shownon the mole basis. In consecutive batch tests, the catalystwas recovered by magnets and washed with EtOH for threetimes. The catalyst was recycled into the autoclave with thefeedstream.

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

Reference:
Article; Chen, Bingfeng; Li, Fengbo; Yuan, Guoqing; Catalysis Letters; vol. 147; 11; (2017); p. 2877 – 2885;,
Ether – Wikipedia,
Ether | (C2H5)2O – PubChem

Some common heterocyclic compound, 92028-21-2, name is 6-Methoxy-[1,1′-biphenyl]-3-amine hydrochloride, molecular formula is C13H14ClNO, 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. HPLC of Formula: C13H14ClNO

To a flask containing 3.91 g (10 mmol) of compound B (Example 13, part b), 3.06 g (13 mmol) of 4-methoxy-3-phenylaniline hydrochloride (from TCI), 0.46 g (0.5 mmol) of tris(dibenzylidineacetone)dipalladium(0), 0.93 g (1.5 mmol) of racemic-2,2′-bis(diphenylphosphino)-1,1′-binaphthyl, and 2.21 g (23 mmol) of sodium tert-butoxide was added 50 mL of toluene, and the mixture was heated at 95 C. for 5.5 hours under an nitrogen atmosphere. The mixture was partitioned between 1.0 M aqueous NaHSO4 and diethyl ether, and the phases were separated. The diethyl ether phase was diluted with one volume of hexanes, and was washed once each with 1.0 M aqueous NaHSO4 and brine, dried over Na2SO4, filtered, and concentrated to a dark oil. The oil was purified by silica gel chromatography, using 12% EtOAc/88% hexanes as eluent, to give compound D as a yellow foam. 1H NMR (300 MHz, DMSO-d6) delta 7.76 (s, 1H), 7.38-7.13 (m, 10H), 6.95-6.81 (m, 7H), 4.28 (s, 2H), 3.61 (s, 3H), 3.16 (m, 2H), 2.53 (m, 2H), 1.29 (s, 9H).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 92028-21-2, its application will become more common.

Reference:
Patent; Moran, Edmund J.; Jacobsen, John R.; Leadbetter, Michael R.; Nodwell, Matthew B.; Trapp, Sean G.; Aggen, James; Church, Timothy J.; US2003/229058; (2003); A1;,
Ether – Wikipedia,
Ether | (C2H5)2O – PubChem

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

General procedure: Triphosgene (0.14 g, 0.48 mmol) was dissolved in anhydrous CH2Cl2 (15 mL) and the mixture was stirred on the ice-bath for 15 min. 3-Bromo-5-(trifluoromethyl)aniline (0.3 g, 1.2 mmol) in anhydrous CH2Cl2 (10 mL) was added dropwise to the above mixture and stirring continued for 20 min. Et3N (0.2 mL, 1.44 mmol) diluted with CH2Cl2 (5 mL) was then added into the mixture. Stirring was continued for 20 min and a solution of Et3N (0.2 mL, 1.44 mmol), 4-pyridin-3-ylaniline (5) (0.2 g, 1.2 mmol) in anhydrous CH2Cl2 (20 mL) was added. After completion of the action, the reaction was quenched with dilute Na2CO3. The organic layer was washed with water and brine, and dried over Na2SO4. After filtration and concentration in vacuo, the residues was purified by silica gel flash chromatography (PE/AcOEt = 6:1) yielding (L1). yield 73%

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; Su, Ping; Wang, Jinfeng; Shi, Yaling; Pan, Xiaoyan; Shao, Ruili; Zhang, Jie; Bioorganic and Medicinal Chemistry; vol. 23; 13; (2015); p. 3228 – 3236;,
Ether – Wikipedia,
Ether | (C2H5)2O – PubChem

Electric Literature of 4457-67-4, A common heterocyclic compound, 4457-67-4, name is 1-Bromo-4-methoxybutane, molecular formula is C5H11BrO, 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.

(4-Methoxybutyl)(4-trifluoromethylphenyl)methanone (II) A dry three neck glass assembly, under dry nitrogen atmosphere, is charged with 150 g (6.17 moles) of magnesium and 2 L of anhydrous tetrahydrofuiran (THF). A small amount of iodine crystals or 1,2-dibromoethane is added to facilitate the initiation of Grignard reaction. The contents of the flask are heated to 75° C. and 975 g (5.84 moles) of 1-bromo-4-methoxybutane is added slowly at such a rate that the reaction maintains a spontaneous gentle reflux until the end of its addition. The Grignard reagent thus formed is cooled to 10 to 20° C. and a solution of 500 g (2.92 moles) of 4-trifluoromethylbenzonitrile in 2 L of tetrahydrofuran is introduced during a period of 1 hour to 2 hours while maintaining the reaction temperature at 16+-2° C. by external cooling, if necessary. Thereafter the temperature is raised gradually to 60 to 70° C. over a period of 1 hour and further continued at that temperature until the reaction has gone to completion. The reaction mass is cooled, then quenched into ice cold hydrochloric acid and the THF layer is separated and concentrated. The aqueous layer is further extracted with dichloromethane which is added to the concentrate of the THF layer. The resulting dichloromethane solution washed with brine, dried over anhydrous sodium sulfate, and the solvent evaporated under reduced pressure to obtain a crude product, which is further purified by high vacuum distillation. The compound (4-methoxybutyl)(4-trifluoromethylphenyl)methanone (II) is obtained in 71.84percent yield (546 g). Analytical data: m.p 40-42° C.(purified by distillation). 1H NMR: (CDCl3, 200 MHz); (delta) 1.66-1.87 (m, -(CH2)2-,4H); 3.04 (t, J=7.26 Hz, -(CH2)-, 2H); 3.33 (s, -OCH3, 3H); 3.43 (t, J=7.26 Hz, -(CH2)-, 2H); 7.72 (d, J=8.30 Hz, 2H); 8.06 (d, J=8.30 Hz, 2H).

The synthetic route of 4457-67-4 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Sun Pharmaceutical Industries Ltd.; US6380436; (2002); B1;,
Ether – Wikipedia,
Ether | (C2H5)2O – PubChem