Category: 20469-65-2

Some common heterocyclic compound, 20469-65-2, name is 1-Bromo-3,5-dimethoxybenzene, molecular formula is C8H9BrO2, 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. category: ethers-buliding-blocks

General procedure: General procedure for the preparation of arylalkynes 2a-q (non-decarboxylative approach, method A). An oven-dried 20 mL Schlenk tube equipped with a magnetic stirring bar and a rubber septum was charged with Pd(OAc)2 (6.7 mg, 30 mumol), tri(p-tolyl)phosphine (18.2 mg, 60 mumol). After purging the vessel with alternating vacuum and nitrogen cycles, degassed THF (3 mL), 1,8-diazabicycloundec-7-ene (450 muL, 3.0 mmol), 2-methylbut-3-yn-2-ol (120 muL, 1.24 mmol) and aryl bromides 1a-q (1.0 mmol) were added via a syringe (solid aryl bromides were added as solution in degassed THF) and the mixture was stirred at 80 C for 6 h. After cooling to rt the mixture was diluted with water (20 mL) and extracted with AcOEt (3 20 mL). Combined organic extracts were washed with H2O (20 mL), saturated aqueous NaCl (20 mL), dried over MgSO4 and concentrated in vacuum. The crude product was purified by silica gel chromatography (eluant hexane/Et2O gradient) affording the corresponding products 2a-q.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 20469-65-2, its application will become more common.

Reference:
Article; Caporale, Andrea; Tartaggia, Stefano; Castellin, Andrea; De Lucchi, Ottorino; Beilstein Journal of Organic Chemistry; vol. 10; (2014); p. 384 – 393;,
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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 20469-65-2 as follows. Safety of 1-Bromo-3,5-dimethoxybenzene

To a solution of 1 (25.0 g, 115.18 mmol) in DCM (200 mL) was added dropwise BBn (21.45 mL, 230.35 mmol) at 0 C, and the mixture was stirred at 25 C for 16 h. The reaction was quenched by MeOH (50 mL) and concentrated under vacuum to afford 2 (21.7 g, 99.7%) as a red oil, which was used directly without further purification.

According to the analysis of related databases, 20469-65-2, the application of this compound in the production field has become more and more popular.

Reference:
Patent; GENENTECH, INC.; F. HOFFMANN-LA ROCHE AG; DRAGOVICH, Peter; PILLOW, Thomas; BLAKE, Robert Anthony; WERTZ, Ingrid; (619 pag.)WO2020/86858; (2020); A1;,
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20469-65-2, name is 1-Bromo-3,5-dimethoxybenzene, 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. Formula: C8H9BrO2

To a mixture of 1-bromo-3,5-dimethoxybenzene (15 g, 69.1 mmol) in dichloromethane (500 ml) at 0 C. was added BBr3 (14.37 ml, 152 mmol) dropwise over 5 minutes at 0 C. The reaction mixture was allowed to warm to room temperature and stirred for 5 hours. The reaction was then cooled to 0 C. and BBr3 (7.2 ml, 76 mmol) added dropwise. The reaction mixture was allowed to warm up to room temperature and stirred overnight. The reaction was again cooled to 0 C. and BBr3 (3.6 ml, 38 mmol) added dropwise. The reaction mixture was allowed to warm up to room temperature and stirred for 4 hours. The mixture was then poured slowly onto ice. When the ice melted, DCM (200 ml) was added and the layers separated. The aqueous was extracted with EtOAc (500 ml) and the layers separated. The combined organics were passed through a through a hydrophobic frit and concentrated. The residue was purified via flash chromatography (ISCO Combiflash Rf, 220 g column, 0-100% ethyl acetate/hexanes) to give the title compound as a yellow oil (19.5 g, 70% purity). MS (m/z) 189.0 (M+).

The synthetic route of 20469-65-2 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; GLAXOSMITHKLINE INTELLECTUAL PROPERTY (NO.2) LIMITED; DOWDELL, Sarah E.; EIDAM, Hilary Schenck; ELBAN, Mark; FOX, Ryan Michael; HAMMOND, Marlys; HILFIKER, Mark A.; HOANG, Tram H.; KALLANDER, Lara; LAWHORN, Brian Griffin; MANNS, Sharada; PHILP, Joanne; WASHBURN, David G.; YE, Guosen; (190 pag.)US2016/340328; (2016); A1;,
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Synthetic Route of 20469-65-2,Some common heterocyclic compound, 20469-65-2, name is 1-Bromo-3,5-dimethoxybenzene, molecular formula is C8H9BrO2, 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.

In a clean dry round bottom flask, l-bromo-3.5-dimethoxybenzene (8.00 g, 36.9 mmol) was added to 300 ml of dry dichloromethane. The solution was cooled down to 0C and BetaIota (25.00 g, 100 mmol) was added dropwise. After 2 hours, the mixture was allowed to warm to room temperature and stirred over night. Methanol (10 ml) was added dropwise to terminate the reaction. The mixture was poured into water and stirred for 2 hours. Then saturated sodium bicarbonate (100 ml) was added and extracted with ethyl acetate. The organic layer was washed with saturated sodium bicarbonate, brine and then dried over Na2S04. The residue, after concentration, was purified using chromatography using ethyl acetate/hexane (1:4 v/v) eluent. Yield = 4.39 g (63%).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 1-Bromo-3,5-dimethoxybenzene, its application will become more common.

Reference:
Patent; POLYMEDIX, INC.; UNIVERSITY OF MASSACHUSETTS; LI, Yan; THAKER, Hitesh; TEW, Gregory N.; LIU, Dahui; PAN, Wenxi; WO2013/90185; (2013); A1;,
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These common heterocyclic compound, 20469-65-2, name is 1-Bromo-3,5-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. SDS of cas: 20469-65-2

A 200-mL two-neck round-bottom flask was charged with anitrogen atmosphere, and to the flask, 1-bromo-3,5-dimethoxybenzene (2.92 g, 13.82 mmol), bis(pinacolato)diboron (5.26 g, 20.73 mmol), Pd(dppf)Cl2?CH2Cl2 (1.56 g, 1.91 mmol) and KOAc (2.10 g, 20.73 mmol) were added into 80 mL of dry DMF. The mixture was stirred at 80C for 60 h under nitrogen. Then, DMF was removed by vacuum distillation, and the residue was extracted with CH2Cl2 (3 20 mL). The CH2Cl2 layer was washed with H2O (2 x 20 mL), dried over anhydrous Na2SO4, filtered and concentrated in vacuo to give a brown crude. The crude product was purified by column chromatography on silica gel (eluent: EtOAc: hexane, 2/3 v/v) to give white compound as a first band. (1.16 g, 88%). 1H-NMR (500 MHz, DMSO) delta(ppm)= 6.95(2H, d, J= 2.6 Hz), 6.57 (1H, t, J= 2.5 Hz), 3.81 (6H, s), and 1.34 (12H, s).

The synthetic route of 1-Bromo-3,5-dimethoxybenzene has been constantly updated, and we look forward to future research findings.

Adding a certain compound to certain chemical reactions, such as: 20469-65-2, name is 1-Bromo-3,5-dimethoxybenzene, 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 20469-65-2, Recommanded Product: 20469-65-2

(1a) 3-Bromo-5-methoxyphenol Commercially available 1-bromo-3,5-dimethoxybenzene (18.74 g, 86.3 mmol) was dissolved in 1-methyl-2-pyrrolidone (100 mL), and sodium thiomethoxide (6.74 g, 96.2 mmol) was added, followed by stirring at 100C for 3 hours under nitrogen atmosphere. The reaction solution was cooled to room temperature, 1N hydrochloric acid (200 mL) was added, and extraction was carried out with diethyl ether (500 mL). The organic layer was washed with saturated brine, and subsequently dried over sodium sulfate. The solvent was distilled off under reduced pressure, and the resulting residue was purified using silica gel column chromatography (elution solvent: ethyl acetate/hexane=20%-25%) to afford the desired compound (15.03 g, yield 86%) as a white solid. 1H-NMR (CDCl3, 400 MHz): delta 3.77 (3H, s), 4.82 (1H, s), 6.33 (1H, t, J=2.4 Hz), 6.61 (1H, t, J=2.0 Hz), 6.66 (1H, t, J=2.0 Hz).

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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. 20469-65-2, name is 1-Bromo-3,5-dimethoxybenzene, This compound has unique chemical properties. The synthetic route is as follows., Quality Control of 1-Bromo-3,5-dimethoxybenzene

Condensation reaction: in with a thermometer, condenser 250 ml bottle to join four 21.9g 5 – bromo – m dimethyl ether {melting point 62 – 66 C; appearance: white solid; nuclear magnetic:1H NMR (CDCl3, 400MHz) delta (ppm) data are as follows: 3.82 (s, 6H, CH3), 6.37 (t, 1H, Ar – H), 6.81 (d, 2H, Ar – H)}, 12.8g bromopropylene, 20.4g triethylamine, 2.2g dppp nickel chloride, 130 ml methyl tert-butyl ether, magnetic stirring, oil bath heating, when the temperature rises to 50 C and maintaining at 4 hours, after the reaction is cooled to ambient temperature, for 60 ml 10% hydrochloric acid aqueous solution washing the reaction liquid, water washed to neutral, the organic layer is distilled under reduced pressure to obtain 17.4g 5 – propenyl – m dimethyl ether {melting point 97 – 100 C; appearance: white solid; nuclear magnetic resonance:1

According to the analysis of related databases, 20469-65-2, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Weifang Xian Da Chemical Co., Ltd.; Li Kai; Wang Guangyue; Yang Qiwei; Zou Yabo; (7 pag.)CN106748673; (2017); 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. 20469-65-2, name is 1-Bromo-3,5-dimethoxybenzene, A new synthetic method of this compound is introduced below., HPLC of Formula: C8H9BrO2

To magnesium (290 g, 12 mmol), 1-bromo-3,5-dimethoxybenzene(0.86 g 4.0 mmol) in THF (20 mL) was added dropwise under nitrogen atmosphere. The mixture was refluxed until magnesium was consumed and cooled to 0C subsequently. To the solution allylbromide (1.2 mL, 15 mmol) was added dropwise. After stirring for 2 h at room temperature the mixture was quenched with sat. NH4Cl aq. was added and extracted with ether and the subsequent purification by flash column chromatography (hexane-ethyl acetate=19 : 1) afforded 1-allyl-3,5-dimethoxybenzene (356 mg, 50%). The mixture of CS2 (35 mL), Al (0.40 g 74 mmol) and I2 (3 g 118 mmol) was refluxed for 2 hs and cooled down to room temperature. To the stirred solution, a solution of 1-allyl-3,5-dimethoxybenzene (0.75 g, 4.2 mmol) in CS2 (35 mL) was added dropwise. The reaction mixture was stirred under reflux for 12 h. The reaction mixture was quenched with water and extracted with Et2O. The combined organic phase washed with 1 M Na2S2O3 aqueous solution and dried over Na2SO4. The solvent was removed and the resulting residue was dissolved in THF, subsequent purification by flash column chromatography (CHCl3-methanol=5 : 1) afforded 2-allylhydroquinone (34 mg, 6%).

The synthetic route of 20469-65-2 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Nishiwaki, Keiji; Ohigashi, Kanae; Deguchi, Takahiro; Murata, Kazuya; Nakamura, Shinya; Matsuda, Hideaki; Nakanishi, Isao; Chemical and Pharmaceutical Bulletin; vol. 66; 7; (2018); p. 741 – 747;,
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These common heterocyclic compound, 20469-65-2, name is 1-Bromo-3,5-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. COA of Formula: C8H9BrO2

The reaction mixture was prepared by adding 3,5dimethoxybromobenzene(1.74 g, 8.0 mmol, 1.0 eq) and catalyst PdCl2(PPh3) 2 (281 mg, 0.4 mmol, 0.05 eq) in a 100 mLSchlenk reaction flask, (20 ml), triethylamine (7 ml, 40 mmol, 5.0 eq) andcotaxyl borane (HBpin) were added to the reaction flask by means of a syringe, (3.5ml, 24.0mmol, 3.0eq), the reaction systemwas heated to 90 C and refluxed for 4 h. The reaction was cooled to room temperature and the reaction solution was pouredinto 20 ml of water to terminate the reaction. The aqueous phase was extracted with ethyl acetate several times. The organicphases were combined and washed once with saturated brine and water, dried over anhydrous magnesium sulfate, And theresulting product was recrystallized from nhexane/ ethyl acetate to give 1.8 g of a white solid in 85% yield. (S, 2H, benzene),6.90 (s, 1H, benzene), 3.84 (s, 6H, OCH3),1.33 (s, 12H, CH3).

The synthetic route of 1-Bromo-3,5-dimethoxybenzene has been constantly updated, and we look forward to future research findings.

Reference:
Patent; TECHNICAL INSTITUTE OF PHYSICS AND CHEMISTRY, CHINESE ACADEMY OF SCIENCES; LI YI, LI YI; HAO, QINGSHAN; CHEN, JINPING; ZENG, YI; YU, TIANJUN; (14 pag.)CN104557552; (2016); B;,
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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. 20469-65-2, name is 1-Bromo-3,5-dimethoxybenzene, This compound has unique chemical properties. The synthetic route is as follows., 20469-65-2

2.171 g of 1-bromo-3,5-dimethoxybenzene and 3.810 g of boronic acid pinacol ester were dissolved in 85 ml of dioxane,2.945 g of potassium acetate and 0.732 g of [1,1′-bis (diphenylphosphino) ferrocene] palladium dichloride were added, and the temperature was raised under argonTo 85 C, stirring for 12 hours after the stop heating, the reaction solution, a small amount of ethyl acetate washing cake, the filtrate concentrated evaporated, residualThe residue was chromatographed (petroleum ether: ethyl acetate = 99: 1-98: 2, V / V) to give 2.462 g of a white solid in 93.2% yield.

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; Chinese Academy Of Sciences Shanghai Pharmaceutical Institute; Duan Wenhu; Geng Meiyu; Zhao Bin; Ding Jian; Ai Jing; Fan Jun; Peng Xia; Yan Wei; Chen Yi; (77 pag.)CN106146493; (2016); A;,
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