Category: ethers-buliding-blocks

402-07-3, 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 402-07-3 as follows.

To a solution of 1-bromo-2-methoxy-4-(trifluoromethyl)benzene (69.0 mg, 0.27 mmol) in dry THF (4 mL) at -78 C under N2 was slowly added N-BuLi (0.11 mL, 2.5 M in N-pentane, 0.27 mmol). After being stirred for 30 min, a solution of 8 (50 mg, 0.11 mmol) in dry THF (1 mL) was added slowly via a syringe. The mixture was stirred for about 2 h and quenched by addition of a saturated aqueous NH4Cl (15 mL) solution, and extracted with EtOAc (10 mL ¡Á 3). The combined organic layers were dried over anhydrous sodium sulfate, filtered and concentrated in vacuum. The residue was purified by flash column chromatography (15% EtOAc/petroleum ether, Rf = 0.2) to give 25 (56 mg, 81%) as a pale brown solid. mp 34.7-36.7 C; 1H NMR (400 MHz, CDCl3) delta 0.001 (s, 3H), 0.07 (s, 3H), 0.83 (s, 9H), 2.41 (s, 3H), 2.94 (d, J = 4.0 Hz, 1H), 3.73 (s, 3H), 4.43 (d, J = 12.0 Hz, 1H), 4.75 (d, J = 12.0 Hz, 1H), 5.81-5.84 (m, 2H), 6.10 (t, J = 3.2 Hz, 1H), 6.34 (d, J = 3.6 Hz, 1H), 6.66 (dd, J = 3.6, 2.0 Hz, 1H), 6.99 (s, 1H), 7.18 (d, J = 8.0 Hz, 1H), 7.24 (d, J = 3.6 Hz, 1H), 7.30 (d, J = 8.0 Hz, 2H), 7.55 (d, J = 8.0 Hz, 1H), 7.85 (d, J = 8.4 Hz, 2H) ppm; 13C NMR (CDCl3, 100 MHz) delta -5.71, -5.67, 18.53, 21.56, 25.92, 25.92, 25.92, 53.27, 55.53, 62.79, 106.87, 106.91, 108.05, 108.43, 111.37, 117.21, 117.25, 121.56, 123.91, 126.96, 127.01, 127.35, 128.40, 129.44, 129.87, 134.75, 134.76, 135.81, 136.29, 145.17, 156.02 ppm; HRMS (M + Na+) calcd. for C31H37F3N2NaO5SSi 657.2042, found 657.2040; IR (KBr) 3383, 3146, 2956, 2929, 2857, 1734, 1594, 1465, 1415, 1377, 1329, 1241, 1175, 1123, 1032, 841, 778, 670 cm-1.

At the same time, in my other blogs, there are other synthetic methods of this type of compound, 402-07-3, and friends who are interested can also refer to it.

Reference:
Article; Cheng, Chunwei; Liu, Yan; Song, Hao; Pan, Lili; Li, Jerry; Qin, Yong; Li, Rongshi; Marine Drugs; vol. 11; 8; (2013); p. 2927 – 2948;,
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7025-06-1, The chemical industry reduces the impact on the environment during synthesis 7025-06-1, name is 1-Bromo-2-phenoxybenzene, I believe this compound will play a more active role in future production and life.

General procedure: Toasolutionofbromide12(a-c)(0.3mmol)and bis(triphenylphosphine)palladium(II)dichloride(9mumol),N-ethyl-N-isopropylpropan-2-amine(0.3mmol)andcopper(I)iodide(0.03mmol)inDMF(1.5ml)wasaddedtheappropriatealkynerelatedalkyne(0.45mmol)andthevesselwasflushedwithargon,sealedandheated(70¡ãC,overnight).Theresultingdarkmixturewascooledtoroomtemperatureandpurifiedbysilicagelchromatographytoafford13(a-d).

The chemical industry reduces the impact on the environment during synthesis 1-Bromo-2-phenoxybenzene. I believe this compound will play a more active role in future production and life.

Reference:
Article; Zhao, Xue Zhi; Hymel, David; Burke, Terrence R.; Bioorganic and Medicinal Chemistry Letters; vol. 26; 20; (2016); p. 5009 – 5012;,
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134364-69-5, 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. 134364-69-5, name is 2,3-Difluoroanisole, This compound has unique chemical properties. The synthetic route is as follows.

To a mixture of l,2-difluoro-3-methoxybenzene (3.0 g, 21 mmol) in anhydrous tetrahydrofuran (40 mL) at -70 C under nitrogen was added dropwise tert-butyllithium (19 mL, 25 mmol, 1.3 M in n-pentane). The mixture was stirred at this temperature for 30 minutes, then NN- dimethylformamide (6.1 g, 83 mmol) was added dropwise at -70 C. The reaction was stirred at – 70 C for another 2 hours. On completion, the mixture was poured into water and extracted with ethyl acetate. The organic layer was dried over anhydrous sodium sulfate and concentrated in vacuo to give compound B-168 (4.0 g, crude) as a yellow solid. LCMS (B): tR=0.661 min., (ES+) m/z (M+H)+ =173.1.

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; FORUM PHARMACEUTICALS, INC.; ACHARYA, Raksha; BURNETT, Duane, A.; BURSAVICH, Matthew, Gregory; COOK, Andrew, Simon; HARRISON, Bryce, Alden; KOENIG, Gerhard; MCRINER, Andrew, J.; (400 pag.)WO2016/100184; (2016); A1;,
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19056-40-7, 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 19056-40-7 as follows.

To a solution of ethyl (2Z)-3-(methylamino)-3-phenylacrylate (4.47 g, 21.77 mmol) in DCM (100 mL) was added 4-bromo-3-methoxyaniline (4 g, 19.80 mmol) and PPTS (5.47 g, 21.77 mmol). The mixture was then heated to reflux for 24h. At this time crude IH NMR revealed nearly complete consumption of the aniline. The reaction was then cooled to r.t.,fltered, and the solvent was removed in vacuo. The crude product was purified on silica (75percent DCM/hexanes) to yield ethyl (2Z)-3- [(4-bromo-3-methoxyphenyl)amino]-3-phenylacrylate (6.5 g, 87percent) which was used as is in subsequent reactions. 1H NMR (500 MHz, CDCl3) ppm: 10.32 (br s, IH), 7.32 (m, 5H), 7.20 (d, J = 8.5 Hz, IH), 6.19 (dd, J = 8.5 Hz, 2.5 Hz, IH), 6.11 (d, J = 2.5 z, IH), 5.03 (s, IH), 4.21 (q, J = 7.0 Hz, 2H), 3.50 (s, 3H), 1.32 (t, J = 7.0 Hz, 3H).

According to the analysis of related databases, 4-Bromo-3-methoxyaniline, the application of this compound in the production field has become more and more popular.

Reference:
Patent; MERCK & CO., INC.; WO2006/119061; (2006); 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. 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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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. 589-10-6, name is (2-Bromoethoxy)benzene, A new synthetic method of this compound is introduced below., 589-10-6

To a stirred solution of methyl isonipecotate (4. 00G, 28.00 mmol) and phenoxyethyl bromide (4. 00g, 20.00 mmol) in acetonitrile (30 ml) was added sodium hydrogen carbonate (7. 00G, 84.00 mmol) and the reaction stirred at 80C for 20 hours. The reaction was cooled, filtered and concentrated under reduced pressure to give a crude brown oil. Purification by column chromatography (7% methanol: dichloromethane) gave the required compound as a light brown oil (4.8g, 65%). oH (270 MHz; CDCL3 ; ME4SI), 1.71-2. 37 (7H, m), 2.79 (2H, t, J 6. 0), 2.93-3. 0 (2H, m) 3.68 (3H, s), 4.10 (2H, t, J 6.0), 6.89-6. 97 (3H, m), 7.24-7. 32 (2H, m). HPLC 99%, m/z (APCI), 264.20 (100% [M+H] +), 232 (40, C14HL802N), 170 (47, C9H1602N).

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; BIOFOCUS PLC; WO2004/58259; (2004); A1;,
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461-82-5, The chemical industry reduces the impact on the environment during synthesis 461-82-5, name is 4-(Trifluoromethoxy)aniline, I believe this compound will play a more active role in future production and life.

N-Bromosuccinamide (3.62 g, 20.34 mmol) was added to a solution of commercially available 4-(trifluoromethoxy)aniline (3.00 g, 1 6.95 mmol) in acetonitrile (30 mL) at 0C. The resulting mixture was allowed to warm to roomtemperature and stirred for 4 hours. The solvent was removed under reduced pressure to give the crude product which was purified by column chromatography eluting in 10% ethyl acetat/hexane to afford the title compound as brown oil (3.6 gm, 83%): 1 H NMR (400 MHz, CDCI3) oe: 4.11 (bs, 2 H), 6.73 (d, 1 H), 6.99 (dd, 1 H), 7.31 (d, 1 H). LC-Ms (m/z): [M-H] = 253.1.

The chemical industry reduces the impact on the environment during synthesis 461-82-5. I believe this compound will play a more active role in future production and life.

Reference:
Patent; ZOETIS SERVICES LLC; WENDT, John; COX, Mark; SHEEHAN, Susan, M.k.; CURTIS, Michael, P.; RESPONDEK, Tomasz; EWIN, Richard, Andrew; KYNE, Graham, M.; JOHNSON, Paul, D.; WO2015/100232; (2015); A2;,
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Adding a certain compound to certain chemical reactions, such as: 437-83-2, name is 3-Fluoro-2-methoxyaniline, 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 437-83-2, 437-83-2

NaNO2 (12.0 g, 1?73 mmol, in 40 m of water) solution was added dropwise to the mixture of 3-fluoro-2-methoxyaniline (20.0 g, 158 mmol) in 200 m of hydrobromic acid (4?7 %) and 100 m of water at -5 o Oc and stirred for 1 hour.This solution was then added slowly to the suspension of cuBr (45.2 g, 315 mmol) in 50 m of hydrobromic acid (4?7 %) at O Oc. The resulting mixture was stirred at o Oc for 1 hour then warmed to so Oc and stirred for 1 hour. The reaction mixture was poured into ice water and extracted with ether (2 X 500 mL). The combined organie layer was washed with brine, dried oyer anhydrous Na2504 and concentrated to giye 1-bromo-3-fluoro-2-methoxybenzene.

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, 3-Fluoro-2-methoxyaniline, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; MERCK SHARP & DOHME CORP.; PASTERNAK, Alexander; DE JESUS, Reynalda, Keh; DING, Fa-xiang; DONG, Shuzhi; FRIE, Jessica; GU, Xin; JIANG, Jinlong; SHAHRIPOUR, Aurash; PIO, Barbara; TANG, Haifeng; WALSH, Shawn; WO2014/126944; (2014); A2;,
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Some common heterocyclic compound, 2674-34-2, name is 1,4-Dibromo-2,5-dimethoxybenzene, molecular formula is C8H8Br2O2, 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. 2674-34-2

K2CO3 (1.13g, 8.19mmol), boronate ester 17 (800mg, 1.78mmol), and dibromoarene 11 (176mg, 0.593mmol) in toluene (20mL), EtOH (4mL) and H2O (2mL) was sparged with Ar for 1h. Pd(PPh3)4 (73mg, 0.063mmol) was added, the mixture was sparged with Ar for an additional 20min, and then heated 90C for 16h. The reaction mixture was cooled to rt and diluted with 50mL of H2O. The reaction mixture was extracted with Et2O (3¡Á50mL). The combined organics were washed with 150mL of brine, dried with Na2SO4, and the solvents were removed under vacuum. The product was isolated via column chromatography as a white solid (433mg, 99%), mp 248-250C. 1H NMR (CDCl3): delta 8.09 (d, J=1.8Hz, 2H), 7.80 (dd, J=8.0, 1.8Hz, 2H), 7.53 (d, J=8.0Hz, 2H), 7.49 (s, 6H), 6.91 (s, 2H), 3.76 (s, 12H), 1.41 (s, 36H). 13C NMR (CDCl3): delta 169.0, 151.3, 150.3, 141.6, 136.8, 132.2, 131.6, 130.3, 129.9, 128.4, 121.8, 121.7, 112.8, 56.0, 51.8, 35.0, 31.5. FTIR (cm-1): 1720.79. UV-vis (CH2Cl2) lowest E abs lambdamax [nm] ( [M-1cm-1]): 337 (22,801). Em. (CH2Cl2) lambdamax [nm]: 424. Anal. Calcd for C52H62O6: C, 79.76; H, 7.98. Found: C, 77.41; H, 8.18.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 2674-34-2, its application will become more common.

Reference:
Article; Dressler, Justin J.; Miller, Sarah A.; Meeuwsen, Brian T.; Riel, Asia Marie S.; Dahl, Bart J.; Tetrahedron; vol. 71; 2; (2015); p. 283 – 292;,
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929-75-9, 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. 929-75-9, name is 1,11-Diamino-3,6,9-trioxaundecane belongs to ethers-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below.

To 3-carboxymethyl-7-[1-(4,4,5,5,6,6,7,7,8,8,9,9,10,10,11,11,11-heptadecafluoroundecyl)-1H-1,2,3-triazol-4-yl]-4-methyl-2H-chromen-2-one (19, 200 mg, 0.268 mmol) and 1,11-diamino-3,6,9-trioxaundecane (8c, 52 mg, 0.27 mmol) in THF (10 mL) at room temperature was added benzotriazole-1-yl-oxytris(dimethylamino)phosphonium hexafluorophosphate (119 mg, 0.268 mmol), and the mixture was stirred at the same temperature for 2 h. The solvent was removed, and the resulting slurry was diluted with saturated aqueous NaHCO3 and extracted with methylene chloride several times. The combined organic layer was washed with brine, dried over magnesium sulfate, and evaporated in vacuo. The residue was chromatographed on a silica gel column with methylene chloride and MeOH (20:1) to give the desired product 21c (84 mg, 34%). Mp 307.4+/-0.2 C; 1H NMR (500 MHz, DMF-d7): delta=8.93 (s, 1H), 8.06 (br t, J=5.8 Hz, 1H), 7.97 (s, 2H), 7.87 (s, 1H), 4.75 (t, J=7.0 Hz, 2H), 3.80 (t, J=5.8 Hz, 2H), 3.69 (s, 2H), 3.65-3.70 (m, 2H), 3.62-3.65 (m, 4H), 3.57-3.60 (m, 4H), 3.36 (q, J=5.8 Hz, 2H), 3.31 (t, J=5.8 Hz, 2H), 2.51 (s, 3H), 2.44-2.57 (m, 2H), 2.32-2.39 ppm (m, 2H); 13C NMR (125 MHz, DMF-d7): delta=169.3, 161.2, 152.9, 149.2, 145.7, 134.2, 126.3, 122.9, 121.3, 120.8, 120.0, 112.4, 70.24, 70.16, 70.09, 70.07, 69.5, 67.1, 49.0, 39.9, 39.3, 27.7, 21.4, 14.9 ppm; IR (ATR, neat): nu=2927, 1703 (CO), 1654 (CO), 1614, 1561, 1200, 1146, 1113, 835 cm-1; MS (ESI): m/z: 920 [M+H+]; HRMS (EI): m/z calcd for C33H34F17N5O6: 919.2238 [M+]; [M+] not found.

The synthetic route of 1,11-Diamino-3,6,9-trioxaundecane has been constantly updated, and we look forward to future research findings.

Reference:
Article; Jeon, Moon-Kook; Kang, Myoung-Ku; Park, Koon Ha; Tetrahedron; vol. 68; 30; (2012); p. 6038 – 6053;,
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