Category: ethers-buliding-blocks

588-96-5, Adding a certain compound to certain chemical reactions, such as: 588-96-5, name is p-Bromophenetole, 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 588-96-5.

General procedure: A mixture of aryl halide (0.25 mmol), phenylboronicacid (0.3 mmol), Na2CO3 (0.25 mmol), PPh3 (0.025 mmol)and Pd(at)PAAs-CD (0.5 mg, 0.2 mol% Pd per mol of arylhalide) were placed into a 10 mL Schlenck tube with1 mL H2O. The reaction mixture was reacted at 80 C for18 h, and the reaction progress was monitored via gaschromatography mass spectrometry (GC-MS). The reactionmixture was allowed to cool to room temperature, andthen 3 mL water was added, and the product was extractedwith ethyl acetate (3 mL ¡Á 3). The organic layers werecombined and dried over anhydrous Na2SO4 and solventswere evaporated via rotary evaporator. The crude productwas purified by column chromatography (200-300 meshsilica) using a mixture of petroleum ether/ethyl acetate(10:1, v:v) as eluent. The structures of the products wereconfirmed by 1H NMR and 13C NMR spectroscopies.

According to the analysis of related databases, 588-96-5, the application of this compound in the production field has become more and more popular.

Reference:
Article; Zhang, Wei; Yao, Zi-Jian; Deng, Wei; Journal of the Brazilian Chemical Society; vol. 30; 8; (2019); p. 1667 – 1677;,
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A common compound: 20781-20-8, name is (2,4-Dimethoxyphenyl)methanamine, 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. 20781-20-8

b) 3-[2-(2,4-dimethoxybenzylamino)pyridin-4-yl]-/V-(1-methylpiperidin-4- yl)imidazo[1,2-b]pyridazin-6-amineTo a solution of 3-(2-chloropyridin-4-yl)-//-(1-methylpiperidin-4-yl)imidazo[1 ,2-b]pyridazin-6- amine (100 mg, 0.29 mmol) and NaO’Bu (39 mg, 0.41 mmol) in DME (2 mL) was added a pre-mixed solution of Pd(OAc)2 (3 mg, 0.015 mmol) and CyPF-‘Bu (8 mg, 0.015 mmol) in DME (1 mL). The reaction mixture was stirred for 5 min before 2,4-dimethoxybenzylamine (68 mg, 0.41 mmol) was added and the mixture heated at 100C for 18 h. The reaction mixture was concentrated in vacuo and purification by column chromatography (EtOAc-2M NH3 in MeOH gradient) gave an off-white solid (77 mg, 56%); 1H NMR (400 MHz, CD3OD) delta ppm 7.94 (d, J=6.0 Hz, 1H), 7.85 (s, 1 H), 7.62 (d, =9.6 Hz, 1 H), 7.51 (s, 1 H), 7.24 (dd, J=5.7, 1.6 Hz, 1H), 7.21 (d, J=8.2 Hz, 1 H), 6.72 (d, J=9.6 Hz, 1 H), 6.54 (d, J=2.3 Hz, 1 H), 6.46 (dd, J=8.2, 2.3 Hz, 1H), 4.43 (s, 2H), 3.83 (s, 3H), 3.82-3.76 (m, 1H), 3.75 (s, 3H), 2.88-2.77 (m, 2H), 2.23-2.09 (m, 7H), 1.68-1.53 (m, 2H); m/z (ES+APCI)+: 474 [M+H]+.

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, 20781-20-8, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; MEDICAL RESEARCH COUNCIL TECHNOLOGY; OSBORNE, Simon; CHAPMAN, Timothy; LARGE, Jonathan; BOULOC, Nathalie; WALLACE, Claire; WO2011/101640; (2011); A1;,
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1462-37-9, The chemical industry reduces the impact on the environment during synthesis 1462-37-9, name is ((2-Bromoethoxy)methyl)benzene, I believe this compound will play a more active role in future production and life.

step Bl – Ethyl phenylcyanoacetate (22, 18.3 mL, 0.1054 mol, Ar1 = Ph) was added dropwise to a suspension of NaH (4.85 g, 0.1213 mol, 60percent dispersion in oil) in DMF (200 mL) cooled to 0 C. The resulting mixture was stirred at 0 C for 30 min then benzyl 2-bromoethyl ether (20 mL, 0.1265 mmol) was added. The reaction mixture was then stirred at 60 C overnight, cooled to RT and partitioned between EtOAc and a saturated aqueous NH4Cl. The aqueous layer was thrice back- extracted with EtOAc. The combined organic extracts were dried (Na2SO4), filtered and evaporated. The residue was purified by Si?2 chromatography eluting with a EtOAc/hexane gradient (5 to 95percent EtOAc) to afford 20 g (60percent) of 24a.

The chemical industry reduces the impact on the environment during synthesis ((2-Bromoethoxy)methyl)benzene. I believe this compound will play a more active role in future production and life.

Reference:
Patent; F. HOFFMANN-LA ROCHE AG; LEMOINE, Remy; MELVILLE, Chris Richard; ROTSTEIN, David Mark; WANNER, Jutta; WO2008/34731; (2008); A1;,
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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;,
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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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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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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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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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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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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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