Author: Jessica.F

These common heterocyclic compound, 588-96-5, name is p-Bromophenetole, 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. Quality Control of p-Bromophenetole

A mixture of 4-bromophenetole (1.0 mmol), phenylboronic acid (1.2 mmol), organic solvents (6 mL), bases (2.0 mmol) and 0.5 mol % of catalyst was stirredat 80 C under air. After the reaction, the catalyst was separated by filtration. The filtrate was dried over Na2SO4 and filtered. The products were quantified by GC-MS analysis (Shimadzu GCMS-QP5050A equipped with a 0.25mm × 30 m DB-WAX capillary column). The typical GCMS analysis program was as follows: initial column temperature 100 C, hold 2 min, ramp temperature to 280 C at 15 C/min, and hold for 5 min.

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

Reference:
Article; Feng, Zhi-Qiang; Yang, Xiao-Li; Ye, Yuan-Feng; Hao, Lin-Yun; Bulletin of the Korean Chemical Society; vol. 35; 4; (2014); p. 1121 – 1127;,
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Reference of 41789-95-1, In the chemical reaction process, reaction time, type of solvent, can easily affect the result of the reaction, thereby determining the yield and properties of the reaction product. An updated downstream synthesis route of 41789-95-1 as follows.

General procedure: To a solution of 2,6-bis(chloromethyl)pyridine (1 mmol) in anhydrous acetonitrile (10 mL) was added cesium carbonate (3 mmol) and the corresponding secondary amine (2.2 mmol). The reaction mixture was heated at reflux for 5 h. The resulting mixture was diluted with water (20 mL) and extracted with ethyl acetate (15 mL) three times. The combined organic layers were washed with brine, dried over anhydrous sodium sulfate, and concentrated in vacuo. The crude was purified by column chromatography with methanol/dichloromethane (100:1, v/v) to give the title compound as a colorless liquid or a white solid.

According to the analysis of related databases, 41789-95-1, the application of this compound in the production field has become more and more popular.

Reference:
Article; Bai, Renren; Liang, Zhongxing; Yoon, Younghyoun; Liu, Shuangping; Gaines, Theresa; Oum, Yoonhyeun; Shi, Qi; Mooring, Suazette Reid; Shim, Hyunsuk; European Journal of Medicinal Chemistry; vol. 118; (2016); p. 340 – 350;,
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Related Products of 41789-95-1,Some common heterocyclic compound, 41789-95-1, name is 1-(3-Methoxyphenyl)-N-methylmethanamine, molecular formula is C9H13NO, 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: A mixture of 2.73 mmol appropriate alkyl halide (i.e., 17a-c, or18a-c), 0.6 g K2CO3 (4.34 mmol), and 0.6 g NaI (4.00 mmol) in ACN(12 mL) was mixed for 5 min in a 30 mL microwave reaction vessel.Then, 8.2 mmol appropriate amine derivative (i.e., 1-6, as shown inScheme 3) was added and the resulting content was mixed foradditional 2 min. The reaction vessel was capped, and insertedinside the microwave instrument (i.e., A CEM Model Single ModeMicrowave Instrument) and heated for 32 min at 105 C at thedynamic mode of the instrument automatically calibrating theradiation and temperature balance with respect to the change inpressure. Then, acetonitrile was distilled out under vacuum andthe residue thus obtained was mixed with 20 mL of K2CO3 solution(5.0%) and this mixture was heated at 60 C for 1 h. Then the mixturewas cooled down to room temperature and the aqueous phasewas extracted 3 times with 20 mL of ethylacetate. Combinedorganic extracts were dried over MgSO4 and concentrated underreduced pressure to give the product (i.e., free base). The free basewas dissolved in 10 mL acetone and HCl gas was continuouslypassed until HCl salt precipitation took place.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 1-(3-Methoxyphenyl)-N-methylmethanamine, its application will become more common.

Reference:
Article; Gulcan, Hayrettin Ozan; Unlu, Serdar; Esiringu, Ilker; Ercetin, Tugba; Sahin, Yasemin; Oz, Demet; Sahin, Mustafa Fethi; Bioorganic and Medicinal Chemistry; vol. 22; 19; (2014); p. 5141 – 5154;,
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54149-17-6, name is 1-Bromo-2-(2-methoxyethoxy)ethane, 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. category: ethers-buliding-blocks

l-Bromo-2-(2-methoxyethoxy)ethane (1.83 g, 10 mmol, diluted in 10 mL of dried DMF) was added dropwise to a stirred mixture of tert- butyl 4-hydroxyphenethylcarbamate (2.61 g, 11 mmol) and NaH (0.44 g, 11 mmol, 60% dispersion in mineral oil) in dry DMF (40 mL) under N2 at 0 C. The reaction was stirred at room temperature for 14 h. After this time, the reaction mixture was stirred at 60 C for 8 h. The reaction was quenched with ice-water and extracted with ethyl acetate. The organic layer was washed with water and brine, dried over sodium sulfate and concentrated in vacuo. The crude product was purified by column chromatography to afford the title compound as colorless oil (2.311 g, 68% yield). NMR (500 MHz, CDCb) S: 7.19- 7.01 (m, 2H), 6.93-6.81 (m, 2H), 4.58 (s, 1H), 4.13 (dd, J= 9.8, 4.9 Hz, 2H), 3.86 (dd, J= 9.5, 5.1 Hz, 2H), 3.79-3.67 (m, 2H), 3.65-3.53 (m, 2H), 3.40 (dd, J= 4.0, 1.8 Hz, 3H), 3.34 (s, 2H), 2.73 (s, 2H), 1.44 (s, 9H).

The synthetic route of 54149-17-6 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; ZHEJIANG VIMGREEN PHARMACEUTICALS, LTD; SUN, Sanxing; ZHAO, Long; HU, Chongbo; CHEN, Zhengshu; YE, Jinqi; (0 pag.)WO2020/2969; (2020); 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. 54149-17-6, name is 1-Bromo-2-(2-methoxyethoxy)ethane, This compound has unique chemical properties. The synthetic route is as follows., Product Details of 54149-17-6

Example 1.2.1 4-Bromo-3,5-dimethylphenol (10.05 g, 50.0 mmol) and K2CO3 (9.0 g, 65.2 mmol) were stirred for 10 minutes in DMF (25 mL). 1-Bromo-2-(2-methoxyethoxy)ethane was added, and the reaction mixture was heated at 45 C. overnight under argon. After cooling to room temperature, the reaction mixture was poured into ~300 mL DCM; filtered off white solids. Flash column (silica; 100% hexane) gave 12.95 g (85% yield) of product 5.

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 54149-17-6.

Reference:
Patent; Nitto Denko Corporaton; US2010/308310; (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. 5467-58-3, name is 1-Bromo-4-methoxynaphthalene, A new synthetic method of this compound is introduced below., Formula: C11H9BrO

The reaction route is as follows:250mL three-necked flask was added 2.66g (0.01mol)1,1-bis (4-aminophenyl) cyclohexane,10.65 g (0.045 mol) of 4-methoxy-1-bromonaphthalene,4.80 g (0.05 mol) sodium tert-butoxide,53g toluene.Nitrogen gas protection 0.09 g (4.0 × 10 -4 mol) of palladium acetate,0.462 g (8.0 × 10 -4 mol) Xantphos,The temperature was raised to 100 C to 108 C and refluxed for 10 hours.Completed the reaction,Add 50g water twice,Dried over anhydrous sodium sulfate,The solvent was removed under reduced pressure to give a tan solid.The above crude product was treated with THF,Ethanol (mass ratio of 3: 6) recrystallization,5.4g white powder was obtained,Yield: 60.5%.

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:
Patent; CECEP Wanrun Co., Ltd.; Hu Zhenyu; Ren Huicai; Cao Yuan; Pang Maoyin; Chen Shuai; Tian Shaozhen; Wang Yonglei; Luo Wei; Hu Baohua; Meng Fanmin; (17 pag.)CN106565507; (2017); A;,
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Adding a certain compound to certain chemical reactions, such as: 102-52-3, name is 1,1,3,3-Tetramethoxypropane, 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 102-52-3, Computed Properties of C7H16O4

1. The starting precursor 2-bromomalonaldehydewas prepared using procedure given in literature [S. Trofimenko, J.Org. Chem. 28(11) (1963), 3243-3245.], [W.J. Tomsho, J.J. McGuire, K. Coward, Org. Biomol. Chem. 3(18) (2005)3388-3398.].To a 100 ml of aqueous solution of 1,1,3,3-tetramethoxypropane (1) (100g, 0.12 M) added concentrated HCl (4.3 ml) and stirred untilit forms homogeneous solution, the temperature of the reaction mixturemaintained was below 35 0C,then slowly added bromine (0.15 M) solution drop wise.After the completeaddition of bromine, stirring was continued for another 30 minutes. Then thereaction mixture was concentrated under vacuum, maintaining the temperature below50 0C until thick slurry was obtained. The obtained slurry waswashed with 200 ml cold water and 100 ml of cold dichloromethane and dried invacuum. Yield: 65%, MP: 148 0C (Lit: 146-147 0C [W.J. Tomsho, J.J. McGuire, K. Coward, Org. Biomol. Chem. 3(18) (2005)3388-3398.],148 0C [M.J. Grard, Compt. Rend. Acad. Sciences. 190 (1930)187:Ann.1930, 13, 336.].

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; Yallur, Basappa Chanabasappa; Katrahalli, Umesha; Krishna, Panchangam Murali; Hadagali, Manjunatha Devagondahalli; Spectrochimica Acta Part A: Molecular and Biomolecular Spectroscopy; vol. 222; (2019);,
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Related Products of 1836-62-0, 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. 1836-62-0, name is 2-(2-Methoxyphenoxy)ethylamine belongs to ethers-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below.

General procedure: To a solution of 2-phenoxy-ethylamine (5 eq.) or 2-(2-methoxyphenoxy-)ethylamine (5 eq.) in 2-methoxyethanol(25 mL per mmol of amine) the appropriate aliphatic chloride33-39 (1 eq.) and KI (cat.) was added. The mixturewas refluxed for18-48 h and concentrated. The residue was suspended in CHCl3and washed with 1M NaOH, brine, dried over anhydrous Na2SO4and concentrated. The crude was purified by flash chromatographyto give the titled compound.

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-(2-Methoxyphenoxy)ethylamine, other downstream synthetic routes, hurry up and to see.

Reference:
Article; Franchini, Silvia; Sorbi, Claudia; Linciano, Pasquale; Carnevale, Gianluca; Tait, Annalisa; Ronsisvalle, Simone; Buccioni, Michela; Del Bello, Fabio; Cilia, Antonio; Pirona, Lorenza; Denora, Nunzio; Iacobazzi, Rosa Maria; Brasili, Livio; European Journal of Medicinal Chemistry; vol. 176; (2019); p. 310 – 325;,
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Synthetic Route of 707-07-3, 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. 707-07-3 name is (Trimethoxymethyl)benzene, 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.

Method 2; Methyl-1-(chloroacetyl)-2-oxoindoline-6-carboxylate (12,0 g; 0,045 mol) is suspended in xylene (60 ml) at ambient temperature. Acetic anhydride (16,2 g; 0,157 mol) is added to this suspension. The mixture is heated to reflux, trimethyl orthobenzoate (20,0 g; 0,108 mol) is added within 40 min and heating is maintained for 4 h. The mixture is cooled down to 0 0C and the mother liquor is separated. The solid is subsequently washed with xylene (14 ml) and a mixture of xylene (8 ml) and ethyl acetate (8 ml). After drying 14,3 g (81 ,0 %) of the “chlorenol” compound are isolated as yellow crystals.

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

Reference:
Patent; BOEHRINGER INGELHEIM INTERNATIONAL GMBH; WO2009/71523; (2009); A1;,
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