Ethers-buliding-blocks

36449-75-9, name is 1-(2-Bromoethyl)-2-methoxybenzene, 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. Product Details of 36449-75-9

Compound 12. l ,4-bis(2-methoxyphenethyl)piperidine A 250 mL round bottom flask was equipped with a magnetic stir bar, and then charged with 5 grams (0.0537 mol) of 4-picoline, 8.77 grams (0.0644 mol) of 2- methoxybenzaldehyde, and 50 mL of acetic anhydride. The reaction mass was heated to reflux and maintained at that temperature for 72 hours. The reaction mixture was then cooled to room temperature, and subjected to silica chromatography. Yield of (E)-4-(2- methoxystyryl)pyridine was 7.15 grams (63%). The 7.15 grams of (E)-4-(2- methoxystyryl)pyridine was then charged into a 500 ml hydrogenation flask, to which was added 100 mL of acetic acid as well as 50 mg of Pt02. The reaction mass was subjected to 45 psi of hydrogen gas, and allowed to react at room temperature for 16 hours. The reaction mixture was then basified, and extracted with dichloromethane, and excess extraction solvent was removed under reduced pressure via rotovap. The residue was then subjected to silica chi matography, yielding 6.1 grams (82.1% yield) of 4-(2-methoxyphenethyl)piperidine. A 100 mL round bottom flask equipped with a magnetic stir bar was then charged with 1.0 grams of 4-(2-methoxyphenethyl)piperidine (0.0046 mol), 1.25 grams of 2- methoxyphenethylbromide (0.0064 mol), 1.87 grams of K2CO3 (0.0135 mol), and 20 mL of DMF as solvent. The reaction mass was then heated to 70 C for 24 hours. The excess DMF was removed via reduced pressure, extracted with water and dichloromethane, the organic layer separated; excess solvent removed under reduced pressure and the residue was subjected to silica chromatography. Yield of l,4-bis(2-methoxyphenethyl)piperidine was 1.04 grams (64.0% yield). 1H NMR (300 MHz, CDC13) delta 1.33-1.59 (m, 7H), 2.35-2.80 (m, 10H), 3.82 (s, 6H), 6.83-7.21 (m, 8H) ppm.

The synthetic route of 36449-75-9 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; UNIVERSITY OF KENTUCKY RESEARCH FOUNDATION; CROOKS, Peter, A.; DWOSKIN, Linda, P.; CULVER, John; NICKELL, Justin, R.; ZHENG, Guangrong; WO2014/144064; (2014); A2;,
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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. 7025-06-1, name is 1-Bromo-2-phenoxybenzene, A new synthetic method of this compound is introduced below., Recommanded Product: 1-Bromo-2-phenoxybenzene

31.7 g (127 mmol) of1-Bromo-2-diphenyl ether,Dissolve in 400 ml of anhydrous THF in a flask which has been dried by heating. Cool the reaction mixture to -78 ¡ã C. At this temperature 55 ml of a 2.5 M solution of n-BuLi in hexane (127 mmol) is slowly added dropwise.The batch was further heated at -70 ¡ã C.Stir for 1 hour.30 g of 2-bromofluorenone (116 mmol)Is dissolved in 100 ml of THF and added dropwise at -70 ¡ã C.Upon completion of the addition, the reaction mixture is warmed slowly to room temperature, warmed up using NH 4 Cl, then evaporated in a rotary evaporator.

The synthetic route of 7025-06-1 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; MERCK PATENT GMBH; MUJICA-FERNAUD, TERESA; MONTENEGRO, ELVIRA; VOGES, FRANK; KROEBER, JONAS VALENTIN; STOESSEL, PHILIPP; (98 pag.)JP2016/505518; (2016); A;,
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Adding a certain compound to certain chemical reactions, such as: 393-15-7, name is 4-Methoxy-3-(trifluoromethyl)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 393-15-7, Recommanded Product: 393-15-7

A. & B. 4-Methoxy-3-trifluoromethylaniline (46.54 g, 0.243 mole), concentrated HCl (87 ml) and water (122 ml) were stirred together and cooled to 0. A solution of sodium nitrite (17.07 g, 0.247 mole) in water (98 ml) was added dropwise, keeping the temperature at 0-5. After the addition was complete, the reaction was stirred at 0-5 for 0.5 hours. Then, all at once, 2-furaldehyde (23.42 g, 0.244 mole) and a solution of copper (II) chloride hydrate (5.60 g) in water (37 ml) were added. The ice bath was allowed to melt gradually as the reaction stirred for 2 days. An oil which had separated was extracted into ethyl acetate (400 ml). The ethyl acetate was washed with water (2*300 ml), dried over MgSO4, treated with Darco and filtered. The solvent was evaporated in vacuo leaving behind a dark oil (55.17 g). The sample required purification by liquid chromatography (solvent: hexane:ethyl acetate 3:1). The yield of purified sample was 16.56 g (25% yield) of 5-(4-methoxy-3-trifluoromethylphenyl)-2-furancarboxaldehyde (B). The IR and NMR confirmed the structure of B.

At the same time, in my other blogs, there are other synthetic methods of this type of compound, 4-Methoxy-3-(trifluoromethyl)aniline, and friends who are interested can also refer to it.

Reference:
Patent; Norwich Eaton Pharmaceuticals, Inc.; US4882354; (1989); A;,
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These common heterocyclic compound, 25245-34-5, name is 2-Bromo-1,4-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. Formula: C8H9BrO2

EXAMPLE 214 1,2-Dihydro-9-methoxy-2,2,4-trimethyl-5-coumarino[3,4-f]quinoline (Compound 314, structure 41 of Scheme XI, where R1 =H, R2 =methoxy) 2,5-Dimethoxyphenylboronic acid (structure 37 of Scheme XI, where R1 =H, R2 =methoxy) This compound was prepared in a manner similar to that of 5-fluoro-2-methoxyphenylboronic acid (EXAMPLE 107) from 1-bromo-2,5-dimethoxybenzene (2.00 mL, 13.3 mmol), n-BuLi (2.5 M in hexanes; 5.34 mL, 13.3 mmol), and trimethylborate (4.5 mL, 40 mmol) to afford 2.43 g (99%) of 2,5-dimethoxyphenylboronic acid which was used without further purification.

The synthetic route of 2-Bromo-1,4-dimethoxybenzene has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Ligand Pharmaceuticals Incorporated; US5688808; (1997); A;,
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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. 102-52-3, name is 1,1,3,3-Tetramethoxypropane, A new synthetic method of this compound is introduced below., SDS of cas: 102-52-3

Concentrated hydrochloric acid (14.5 ml, 87 mmol) was added dropwise to the stirred mixture of 2-iodophenylhydrazine (14 g, 60 mmol) and malondialdehyde bis(dimethyl acetal) (12 g, 72 mmol) at 0 C. After the addition completed, the reaction mixture was stirred for 2 h at room temperature, and water (20 ml) was added. Then, the reaction mixture was neutralized with NaOH solution (1 M). The solution was extracted with ethyl acetate (3 * 30 ml). The organic phases were combined, and dried over anhydrous MgSO4. After the solvent was removed under reduced pressure, red oil was obtained. Yield: 11.8 g (73%). 1H NMR: delta 6.49 (t, J = 2.1 Hz, 1H, H4 of pyrazole), 7.16 (dt, J = 2.0 Hz, J = 7.9 Hz, 1H), 7.41-7.48 (m, 2H), 7.98 (dd, J = 0.9 Hz, J = 8.0 Hz, 1H) (C6H4), 7.73 (d, J = 2.3 Hz, 1H), 7.77 (d, J = 1.4 Hz, 1H) (H3 and H5 of pyrazole) ppm. 13C NMR: delta 94.4, 106.6, 128.2, 129.0, 130.2, 131.1, 140.1, 140.8, 143.4 (C6H4 and carbons of pyrazole) ppm. HRMS-ESI (m/z): 292.9547 (Calc. for C9H7IN2Na: 292.9552, [M + Na]+, 100%).

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; Cheng, Cai-Hong; Chen, Dan-Feng; Song, Hai-Bin; Tang, Liang-Fu; Journal of Organometallic Chemistry; vol. 726; (2013); p. 1 – 8;,
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Related Products of 89521-55-1, A common heterocyclic compound, 89521-55-1, name is 3-(Benzyloxy)benzene-1,2-diamine, molecular formula is C13H14N2O, 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 solution of Compound (6) (1.0 g), 3-(benzyloxy)-1,2-benzenediamine (817 mg) and 1-hydroxybenzotriazole (567 mg) in N,N-dimethylformamide (19 mL) was added 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride (804 mg). After stirring for 6 hrs, saturated aqueous NaHCO3 (20 mL) and water (80 mL) were added to the reaction mixture. The resulting precipitate was collected by filtration and washed with water. To a mixture of this product in acetic acid (7 mL) was added a solution of hydrogen chloride in acetic acid (13 mL). After stirring at 100 C. for 1 hour, the resulting mixture was cooled to 4 C. and diluted with ethyl acetate (40 mL). The resulting precipitate was collected by filtration and washed with ethyl acetate. To a solution of this product, O-tetrahydro-2H-pyran-2-ylhydroxylamine (1.5 eq.) and 1-hydroxybenzotriazole (1.5 eq.) in N,N-dimethylformamide (11 mL) was added 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide (1.5 eq.) at 4 C. The mixture was warmed to ambient temperature and stirred for 8 hrs. The reaction mixture was added saturated NaHCO3 (11 mL) and water (44 mL). A resulting precipitate was filtered and the filtrate was extracted with ethyl acetate. The organic layer was washed with H2O and brine, dried over MgSO4, filtered and evaporated in vacuo. The crude product was treated with trifluoroacetic acid to give Compound E120 (52 mg). 1H-NMR (300 MHz, DMSO-d6, delta): 4.43 (2H, s), 6.46 (1H, d, J=16 Hz) 6.86 (1H, d, J=8 Hz), 7.12(1H, d, J=8 Hz), 7.23-7.30 (1H, m), 7.39-7.62 (5H, m);

The synthetic route of 89521-55-1 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; FUJISAWA PHARMACEUTICAL CO., LTD.; US2004/229889; (2004); A1;,
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Reference of 5414-19-7, These common heterocyclic compound, 5414-19-7, name is 1-Bromo-2-(2-bromoethoxy)ethane, 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.

Intermediate 8 (1.70 g, 8.015 mmol) was dissolved in N, N-dimethylformamide (20 mL)Placed in a sealed tube,2,2′-dibromodiethyl ether (1.4 mL, 8.816 mmol) and N, N-diisopropylethylamine (2.7 mL, 16.03 mmol) were added.The reaction was heated to 100 C,Stir for 16 hours.Cooled to room temperature,Ethyl acetate was added,Washed,The organic phase is dried,Filtered and concentrated under reduced pressure,The crude product was purified by column chromatography,To give intermediate 9 (2.23 g) in 42% yield.

Statistics shows that 1-Bromo-2-(2-bromoethoxy)ethane is playing an increasingly important role. we look forward to future research findings about 5414-19-7.

Reference:
Patent; Shanghai Hansoh BioMedical Co., Ltd.; Jiangsu Hansoh Pharmaceutical Group Co., Ltd.; Zhao, Zhiming; Wu, Chenchen; Yu, Hongping; Xu, Yaochang; Pan, Zhongzong; Bao, Rudi; (26 pag.)CN106349180; (2017); A;,
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Synthetic Route of 41406-00-2, 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. 41406-00-2, name is 3-Isopropoxyaniline, This compound has unique chemical properties. The synthetic route is as follows.

EXAMPLE 86; N-[(2-Cyclohexyl-4-hydroxy-1-{3-[(1-methylethyl)oxy]phenyl}-6-oxo-1,6-dihydro-5-pyrimidinyl)carbonyl]glycine; 86a) 2-Cyclohexyl-6-hydroxy-3-{3-[(1-methylethyl)oxy]phenyl}-4(3H)-pyrimidinone; 1M Dimethylaluminium chloride in hexane (2.75 mL, 2.75 mmol) was added to a stirred solution of 3-isopropoxyaniline (0.378 g, 2.50 mmol) and cyclohexanecarbonitrile (0.328 g, 3.00 mmol) in toluene (2 mL) and the mixture stirred for 15 min at room temperature under nitrogen, then microwaved at 150 C. for 30 min. After cooling, the solvent was removed under reduced pressure and diethyl malonate (1.52 mL, 10.0 mmol) added, followed by 2-methoxyethanol (5 mL) and methanolic sodium methoxide (2.30 mL, 10.0 mmol) and the mixture refluxed under nitrogen for 18 h, then cooled and poured into water (70 mL). The mixture was washed with ether, then acidified to pH 1 with 6M aqueous hydrochloric acid and extracted again with ethyl acetate. The extracts were washed with water, brine, dried (MgSO4) and evaporated under reduced pressure. The residue was chromatographed (silica gel, 1-9% methanol/dichloromethane) and the product triturated with ether. The solid was collected, washed with ether and dried to give the title compound (0.117 g, 14%) as a white solid. 1H NMR (400 MHz, DMSO-d6) delta ppm 0.78-0.94 (m, 2 H) 1.04-1.17 (m, 1 H) 1.24 (d, J=6.06 Hz, 3 H) 1.28 (d, J=6.06 Hz, 3 H) 1.41-1.59 (m, 3 H) 1.59-1.84 (m, 4 H) 2.16 (tt, J=11.53, 3.16 Hz, 1 H) 4.66 (sept, J=5.98 Hz, 1 H) 5.30 (s, 1 H) 6.78-6.86 (m, 1 H) 6.91-6.96 (m, 1 H) 6.98-7.05 (m, 1 H) 7.40 (t, J=8.08 Hz, 1 H) 11.31 (br. s., 1 H).

The chemical industry reduces the impact on the environment during synthesis 3-Isopropoxyaniline. I believe this compound will play a more active role in future production and life.

Reference:
Patent; Shaw, Antony N.; Duffy, Kevin J.; Tedesco, Rosanna; Wiggall, Kenneth; US2008/171756; (2008); A1;,
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Some common heterocyclic compound, 446-59-3, name is 2-Bromo-1-fluoro-3-methoxybenzene, molecular formula is C7H6BrFO, 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. Recommanded Product: 446-59-3

2-Bromo-3-fluoro anisole (10 g, 48.77 mmol) was dissolved in DCM (200 mL) and cooled to about -78 C. To the solution was added BBr3 (11.53 mL, 121.9 mmol) in one portion. The mixture was warmed to r.t. and stirred overnight. The mixture was partitioned between water and DCM (50 mL), and the aqueous layer was back extracted with DCM (200 mL). The combined organics were dried (NaSO4), filtered and concentrated to give about 9.32 g of the product as a dark oil. MS found 188.9 (M-1)

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 446-59-3, its application will become more common.

Reference:
Patent; Briner, Karin; Doecke, Christopher William; Mancuso, Vincent; Martinelli, Michael John; Richardson, Timothy Ivo; Rothhaar, Roger Ryan; Shi, Qing; Xie, Chaoyu; US2004/82590; (2004); A1;,
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Related Products of 36865-41-5, 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. 36865-41-5, name is 1-Bromo-3-methoxypropane, This compound has unique chemical properties. The synthetic route is as follows.

General procedure: To a stirred solution of 33b (0.68 g, 1.74 mmol) and K2CO3 (322 mg, 2.33 mmol) in DMF (15 mL) was added 2-chloro-N,N-diethylacetamide (0.31 g, 2.07 mmol) and the mixture was stirred at room temperature for 2 h, at 50 C for 30 min, and at 80 C for 1 h. Then, additional 2-chloro-N,N-diethylacetamide (0.30 g, 2.01 mmol) was added to the mixture, which was stirred at 80 C for additional 30 min. After being cooled to room temperature, the reaction was acidified with 1 M HCl, and extracted with EtOAc, and the combined organic layer was washed with sat. NaHCO3 and brine, dried over MgSO4, filtered and concentrated under reduced pressure. The residue was purified by silica gel chromatography (hexane-EtOAc, 9:1 to 1:2) to give crude 7c (1.39 g, quant.) as a white solid.

The chemical industry reduces the impact on the environment during synthesis 1-Bromo-3-methoxypropane. I believe this compound will play a more active role in future production and life.

Reference:
Article; Rikimaru, Kentaro; Wakabayashi, Takeshi; Abe, Hidenori; Tawaraishi, Taisuke; Imoto, Hiroshi; Yonemori, Jinichi; Hirose, Hideki; Murase, Katsuhito; Matsuo, Takanori; Matsumoto, Mitsuharu; Nomura, Chisako; Tsuge, Hiroko; Arimura, Naoto; Kawakami, Kazutoshi; Sakamoto, Junichi; Funami, Miyuki; Mol, Clifford D.; Snell, Gyorgy P.; Bragstad, Kenneth A.; Sang, Bi-Ching; Dougan, Douglas R.; Tanaka, Toshimasa; Katayama, Nozomi; Horiguchi, Yoshiaki; Momose, Yu; Bioorganic and Medicinal Chemistry; vol. 20; 10; (2012); p. 3332 – 3358;,
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