Month: November 2020

1462-37-9, name is ((2-Bromoethoxy)methyl)benzene, 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. 1462-37-9

To a stirred solution of 3,5-dimethyl lH-pyrazole-3,5-dicarboxylate (10 g, 54.30 mmol, 1 equiv.) and [(2-bromoethoxy)methyl] benzene (12.8 g, 59.51 mmol, 1.096 equiv.) in MeCN (200 mL) was added K2CO3 (11.3 g, 81.46 mmol, 1.5 equiv.) at room temperature under nitrogen atmosphere. The resulting mixture was stirred for 4 h at 90 ¡ãC. The mixture was allowed to cool down to room temperature and then quenched with water. The resulting mixture was extracted with EtOAc and the combined organic layers were dried over anhydrous Na2S04. After filtration, the filtrate was concentrated under reduced pressure and the residue was purified by silica gel column chromatography, eluting with PE/EtOAc (10: 1) to afford the title compound as a yellow oil in 96.22percent yield.

Statistics shows that 1462-37-9 is playing an increasingly important role. we look forward to future research findings about ((2-Bromoethoxy)methyl)benzene.

Reference:
Patent; IDEAYA BIOSCIENCES, INC.; ALAM, Muzaffar; BECK, Hilary Plake; DILLON, Michael Patrick; GONZALEZ-LOPEZ, Marcos; RICO, Alice Chen; SUTTON, JR., James Clifford; (317 pag.)WO2019/18562; (2019); A1;,
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A common compound: 2752-17-2, name is 2,2′-Oxydiethanamine, belongs to ethers-buliding-blocks compound, it can change the direction of chemical reaction, and react with certain compounds to generate new functional products. A new synthetic method of this compound is introduced below. 2752-17-2

For the synthesis of H2L, salicylic aldehyde (10 mM, 1.22 g) in EtOH (5 mL) was added dropwise to 5mL of an EtOH solution of 3-oxapentane-1,5-diamine (5 mM, 0.52 g). After completion of addition, the solution was stirred for an additional 4 h at 78 C. After cooling to room temperature, the precipitate was filtered. The product was dried in vacuo, giving a yellow crystalline solid. Yield: 1.19 g (68.5%).

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, 2752-17-2, other downstream synthetic routes, hurry up and to see.

Reference:
Article; Wu, Huilu; Pan, Guolong; Bai, Yuchen; Wang, Hua; Kong, Jin; Shi, Furong; Zhang, Yanhui; Wang, Xiaoli; Journal of Coordination Chemistry; vol. 66; 15; (2013); p. 2634 – 2646;,
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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. 1535-75-7, name is 2-(Trifluoromethoxy)aniline, A new synthetic method of this compound is introduced below., 1535-75-7

General procedure: The benzoic acid 1 (1.50 g, 7.46 mmol) was refluxed in neat thionyl chloride (2 mL) for 2 h then allowed to cool to rt. The excess thionyl chloride was removed under reduced pressure to yield the crude acid chloride. A solution of anilines in DCM (10 mL) was added to a solution of the crude acid chloride in DCM (10 mL), followed by triethylamine (2.25 mL). The mixture was stirred at room temperature under argon for 3 h, after which the solvent was removed. The residue was purified by recrystallization (petroleum ether- ethyl acetate) to afford the product.

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; Liu, Fang; Venter, Henrietta; Bi, Fangchao; Semple, Susan J.; Liu, Jingru; Jin, Chaobin; Ma, Shutao; Bioorganic and Medicinal Chemistry Letters; vol. 27; 15; (2017); p. 3399 – 3402;,
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588-96-5, name is p-Bromophenetole, 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. 588-96-5

General procedure: The Teflon-lined sealed tube (20 mL) was charged with a 1,4-dioxane solution of sodium fluoroalkoxide RFONa [freshly prepared from fluoroalkanol RFOH (3.3(n + 1) mmol) and Na (3.0 (n + 1) mmol) in 1,4-dioxane (5 mL)], unactivated arylbromide ArBrn (3.0 mmol), CuBr (0.3n mmol) and DMF (3.0n mmol). The sealed tube was heated to 110 C and stirred for 6 h. After the completion of reaction, the concentration of the mixture in vacuo gave a residue, to which was added methyl tert-butyl ether (MTBE, 20 mL) and diluted hydrochloric acid (10 mL, 1.0 mol/L). The organic phase was separated, and the aqueous phase was extracted with MTBE (10 mL 9 3). The combined organic layer was dried over anhydrous MgSO4, andthen concentrated in vacuo to supply a crude product. Lastly, the purification of the crude product provided the desired product via column chromatography on silica gel (eluents: petroleum ether/ethyl acetate 20:1).

Statistics shows that 588-96-5 is playing an increasingly important role. we look forward to future research findings about p-Bromophenetole.

Reference:
Article; Guo, Ying; Li, Yu-Dao; Chen, Cheng; Zhao, Jian-Hong; Liu, Hong-Wei; Liao, Dao-Hua; Ji, Ya-Fei; Research on Chemical Intermediates; vol. 42; 3; (2016); p. 2525 – 2537;,
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3401-47-6,Some common heterocyclic compound, 3401-47-6, name is 1-Bromo-2-methoxynaphthalene, molecular formula is C11H9BrO, 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.

237 g of 1-bromo-2-methoxynaphthalene (1 mol) and 200 ml of toluene were added to a 2000 ml reaction flask, and water was refluxed at 110 C. After the water was separated, 1000 ml of THF was added to the reaction flask under N 2 protection.Add 344g of triisopropyl borate (liquid, 1.8mol) dropwise (addition time is 30 minutes), cool down to -65 ~ -60 C, and add dropwise (addition time is 60 minutes)450 ml of n-butyllithium (1.125 mol), reacted at -65 to -60 C for 20 minutes; at this time, it was monitored by HPLC.1-Bromo-2-methoxynaphthalene is less than 5%, 2-methoxynaphthalene-1-boronic acid content is greater than 77%,250 ml of 5% hydrochloric acid solution was added to the reaction solution, the reaction was quenched, the layer was static, and the upper layer was an organic layer. The organic layer was washed once with water (500 ml of water), and the layer was statically layered, and the organic layer was taken at 55-65 C. At -0.05 Mpa, the solvent was decompressed under reduced pressure to 10% of the original volume (in a slurry state), and 400 ml of DCM was added thereto, stirred uniformly, and then vacuum filtered at -0.05 Mpa, and the filter cake was dried at a constant pressure of 50 C to a constant weight. White powder2-methoxynaphthalene-1-boronic acid 120 g (0.594 mol), content 99.2%; yield: 58.9%.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 3401-47-6, its application will become more common.

Reference:
Patent; Silver Pounuo New Materials Co., Ltd.; Li Xianyue; Song Wenzhi; Wu Qinglai; Guo Lei; Fu Chunrong; Yu Peng; (8 pag.)CN109305981; (2019); A;,
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2216-69-5, 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. 2216-69-5, name is 1-Methoxynaphthalene, This compound has unique chemical properties. The synthetic route is as follows.

Bromination using NBS has been found to be applicable for use with a wide range of aromatic starting materials or substrates, as is EPO summarized in Table 1 . For example, anisole can be brominated by use of 1 equivalent of NBS in the presence of 5 mol % of ZrCI4 at -78 0C to afford p- bromoanisole in 98% yield as sole product (Table 1 , Entry 1 ). However, in the absence of ZrCI4 the halogenation does not proceed, even at room temperature (Table 1 , Entry 1 ).[00111] All of the substrates shown in Table 1 were brominated to give the corresponding monobromo products in excellent yield and regioselectivity. In most cases, the reaction can proceed at very low temperature and no further purification is necessary. In addition. Table 1 reveals that the halogenation of the present invention is compatible with a variety of substituents.Table 1 ZrCI4 Catalyzed Bromination of Aromatic Compounds EPO (5 mol %), CH2CI2 (4d See spectroscopic data for characterization.

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; UNIVERSITY OF CHICAGO; JAPAN SCIENCE AND TECHNOLOGY AGENCY; WO2007/27917; (2007); A2;,
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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. 2734-70-5, name is 2,6-Dimethoxyaniline, This compound has unique chemical properties. The synthetic route is as follows., 2734-70-5

To a solution of 2,6-dimethoxyaniline (0,5 g, 3 rnrnol) and 4-fluorobenzonitrile (0.5 g, 4 mmol) in toluene (10 ml) at 0 ¡ãC was added dropwise TMS-OTf (0.65 ml, 3.6 rnmol). The resulting mixture was stirred at 0 ¡ãC for 10 mm and heated to 110¡ãC for 15 hrs. Thereaction mixture was cooled to 0 ¡ãC, quenched with 1.5 M Na2T-fPO4 (10 mL) solution anddiluted with EtOAc. The organic layer was washed with 1.5 M Na2HPO4 solution and driedover sodium sulfate, concentrated to give a brown oil. The residue was purified by a silica gel (80 g) column and was eluted with 0-100percent 0.5percent TEA/EtOAc in DCM. Fractions containing compound 37a were combined and the solvent removed to give 37a (0.55 g, 2.0 mrnol, 61 percent yield) an off white solid. 1HNMR (500MHz, CDC13) 7.96 (br s, 2H), 7.10 (br s, 2H), 7.02(t, J 8.0 Hz, 1H), 6.64 (d, J¡ã¡ã 7.7 Hz, 2H), 4.68 (hr s, 2H), 3.80 (s, 6H).

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; BRISTOL-MYERS SQUIBB COMPANY; MENG, Wei; CHAO, Hannguang J.; FINLAY, Heather; LAWRENCE, R., Michael; MYERS, Michael C.; (154 pag.)WO2017/96130; (2017); A1;,
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Some common heterocyclic compound, 64115-88-4, name is 1-Bromo-2-(trifluoromethoxy)benzene, molecular formula is C7H4BrF3O, 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. 64115-88-4

2.0 g of 1-bromo-2-(trifluoro-methoxy)benzene (8.3 mmol) were dissolved in 30 ml of dichloromethane. At 0-50C, 1.06 g of chlorosulfonic acid (9.13 mmol), dis- solved in 3 ml of dichloromethane, were added dropwise. The reaction mixture was stirred for 30 min at room temperature. Additional 5.5 equivalents of chloro? sulfonic in dichloromethane were added to drive the reaction to completion. Standard work-up was followed and silica gel chromatography with n-heptane- dichloromethane (6:4) as eluent gave 2.19 g of the title compound.1H-NMR (CDCI3, 400 MHz): delta [ppm] 8.3 (d, 1 H), 8.05 (dd, 1 H), 7.5 (dd, 1 H).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 64115-88-4, its application will become more common.

Reference:
Patent; ABBOTT GMBH & CO. KG; WO2006/40182; (2006); A1;,
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458-50-4, Name is 4-Bromo-3-fluoroanisole, 458-50-4, 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.

General procedure: Benzimidazole (5 mmol), 1-bromo-2-fluorobenzene derivatives (15 mmol, 2 equiv) and tripottasium phosphate (5.31g, 25 mmol, 5 equiv) were dissolved in DMF (30 mL). The mixture was stirred at 150 C. The reaction time was determined by monitoring with TLC. The reaction mixture was diluted with CH2Cl2 (50 mL) and water (50 mL). The phases were separated, and the aqueous layer was extracted with CH2Cl2 (2 ¡Á 30 mL). The combined organic layerswere washed with water (3 ¡Á 50 mL), dried with MgSO4, and concentrated under reduced pressure. The residue was purified by silica gel chromatography (n-hexane/AcOEt).

Statistics shows that 4-Bromo-3-fluoroanisole is playing an increasingly important role. we look forward to future research findings about 458-50-4.

Reference:
Article; Matsumura, Mio; Kitamura, Yuki; Yamauchi, Arisa; Kanazawa, Yoshitaka; Murata, Yuki; Hyodo, Tadashi; Yamaguchi, Kentaro; Yasuike, Shuji; Beilstein Journal of Organic Chemistry; vol. 15; (2019); p. 2029 – 2035;,
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929-75-9, name is 1,11-Diamino-3,6,9-trioxaundecane, 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. 929-75-9

To 2- [2- [2- [2-AMINOETHOXY] ethoxy] ethoxy] ethylamine (23 (, 0.5 g, 2.6 mmol), dissolved in CH2C12 (50 mL), was added triethylamine (0.36 mL, 100 mol%) and Boc20 (0. 55 g, 100 mol%). The reaction mixture was stirred for 4 hours and concentrated to dryness. The resulting residue was purified by silica gel column chromatography eluting with 9: 1: 0.1 chloroform : methanol: ammonium hydroxyde to give 0.26 g (34% yield) of the title compound 24. H NMR (CDC13, 300 MHz) 8 3.66 (m, 8H), 3.57 (m, 4H), 3.28 (m, 2H), 2.90 (t, 2H), 1.63 (bs, 2H), 1.47 (s, 9H).

Statistics shows that 929-75-9 is playing an increasingly important role. we look forward to future research findings about 1,11-Diamino-3,6,9-trioxaundecane.

Reference:
Patent; DIHEDRON CORPORATION; WO2005/30258; (2005); A2;,
Ether – Wikipedia,
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