Category: ethers-buliding-blocks

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. 126940-10-1, name is 1-Fluoro-3-(methoxymethoxy)benzene, This compound has unique chemical properties. The synthetic route is as follows., COA of Formula: C8H9FO2

A solution of 270 ML (430 MMol) n-butyllithium (1.6 M in hexanes) in 800 ML tetrahydrofuran was cooled to -78C. To this solution was added a solution of 60 gm (384 MMol) 1-(methoxymethoxy)-3-fluorobenzene in 100 ML tetrahydrofuran over 30 minutes.. The resulting mixture was stirred for 1 hour and was then rapidly quenched with 67.5 gm (423 MMol) bromine.. The reaction mixture was stirred for 30 minutes and was then partitioned by the addition of 500 ML methyltert-butyl ether and 300 ML saturated aqueous sodium thiosulfate.. The organic phase was dried over sodium sulfate and concentrated under reduced pressure.. The residual oil was distilled (kugelrorh, 70-100C, 0.1 torr) to provide 81.7 gm (91%) of the desired compound as a colorless oil.

Chemical properties determine the actual use. Each compound has specific chemical properties and uses. We look forward to more synthetic routes in the future to expand reaction routes of 126940-10-1.

Reference:
Patent; ELI LILLY AND COMPANY; EP1204660; (2004); B1;,
Ether – Wikipedia,
Ether | (C2H5)2O – PubChem

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. 106658-14-4, name is 4-Methoxybenzene-1,2-diamine hydrochloride, A new synthetic method of this compound is introduced below., Safety of 4-Methoxybenzene-1,2-diamine hydrochloride

To a solution of 1,2-diamino-4-methoxybenzene hydrochloride (2 g) in acetonitrile (20 mL) was added dropwise tert-butylnitrite (1.35 mL) at 0 C. After 4 hours at room temperature, the mixture was concentrated under reduced pressure to a solid residue, which was then dissolved in water. The aqueous solution was neutralized with a saturated solution of sodium bicarbonate and extracted with ethyl acetate. The organic phase was washed with brine, dried over anhydrous sodium sulfate, filtered and the filtrate concentrated under reduced pressure to afford 5-methoxy-1H-benzotriazole as an off-white solid (1.2 g, 85%). MS (ES): M/Z [M+H]=150.

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; Soll, Mark David; Hir de Fallois, Loic Patrick Le; Huber, Scot Kevin; Lee, Hyoung Ik; Wilkinson, Douglas Edward; Jacobs, Robert Toms; Beck, Brent Christopher; US2010/125089; (2010); A1;,
Ether – Wikipedia,
Ether | (C2H5)2O – PubChem

Reference of 104566-41-8, 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 104566-41-8 as follows.

Another procedure involves use amide formation using the acid chloride as shown in the following reaction. To 4-biphenylacetic acid (2.5 g) in a flask, thionylchloride (20 ml) was added and heated to reflux for 1 h, cooled, and the excess thionylchloride removed under vacuum to dryness, then the produced crude acid chloride 2.8 g, dissolved in dry DCM (dichloromethane) (30 ml), and added drop wise at 0 C. to equimolar amount of the 3-benzyloxybenzylamine solution in DCM (10 ml) with (1.5 mol) of triethylamine (TEA) and stirred for 5 hrs, then poured onto acidified cold water, the organic layer washed with water, brine and the solvent removed under reduced pressure to give the target amide in 80% yield. 1H NMR (DMSO, 500 MHz): delta 8.58 (t, J=12 Hz 1H), 7.60-7.57 (m, 4H), 7.44-7.29(m, 10H), delta 7.21(t, J=16.5 Hz, 2H), 6.85(d, J=6.5 Hz, 2H), 6.81(d, J=8.0 Hz, 1H), 5.00(s, 2H), 4.24(d, J=6 Hz, 2H), 3.51(s, 2H).

According to the analysis of related databases, 104566-41-8, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Hangauer, David G.; US2006/160800; (2006); A1;,
Ether – Wikipedia,
Ether | (C2H5)2O – PubChem

Application of 4457-67-4, 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 4457-67-4 as follows.

b) 2-(4-Methoxybutoxy)-benzoic acid ethyl ester A solution of 4-methoxybutyl bromide (4.5 g) in acetonitrile (15 ml) is added dropwise under reflux to a mixture of salicylic acid ethyl ester (2.63 ml), powdered potassium carbonate (3.10 g) and potassium iodide (10 mg) in acetonitrile (50 ml), and the reaction mixture is then stirred overnight. After cooling, filtration is carried out, the filtrate is concentrated and the residue is added under a high vacuum. The title compound (4.4 g), Rf (C)=0.28, is obtained in the form of a pale-yellow oil.

According to the analysis of related databases, 4457-67-4, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Ciba-Geigy Corporation; US5641778; (1997); A;,
Ether – Wikipedia,
Ether | (C2H5)2O – PubChem

Related Products of 6850-60-8,Some common heterocyclic compound, 6850-60-8, name is (4-Ethoxyphenyl)methanamine, molecular formula is C9H13NO, 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.

Synthesis of 5-Bromo-N- (4-ethoxybenzyl) -3-nitropyridin-2-amine (compound 62-2)[0000214] To a stirred solution of 2,5-dibromo-3- nitropyridine (1 g, 3.5 mmol, 1 equiv) in ethanol (10 mL) was added a (4-ethoxyphenyl)methanamine (580 IlL, 3.9 mmol, 1.1 equiv) and triethylamine (1 mL, 7.1 mmol, 2 equiv) . The reaction mixture was allowed to stir at room temperature for 18 hours, at which time LC-MS indicated the reaction was complete. The suspension was filtered and the solid washed with ethanol (2 x 5 mL) to produce compound 62-2 as a yellow solid (1.1 g, 92% yield)

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

Reference:
Patent; SIGA TECHNOLOGIES, INC.; DAI, Dongcheng; BURGESON, James, R.; AMBERG, Sean, M.; HRUBY, Dennis, E.; WO2013/123215; (2013); A2;,
Ether – Wikipedia,
Ether | (C2H5)2O – PubChem

Adding a certain compound to certain chemical reactions, such as: 6052-10-4, name is 4,4′-(Ethane-1,2-diylbis(oxy))dianiline, 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 6052-10-4, Recommanded Product: 6052-10-4

The TGAE was synthesized (Fig. 1.) according to the reported procedure [23]. A 250-mL two-neck round bottom flask, equipped with magnetic stirrer, thermometer and condenser was charged with 4-(2-(4-aminophenoxy)ethoxy)benzenamine ethane (5.0 g, 0.02 mol), 40 mLtoluene and 1.5 mL 50% manganese nitrate aqueous solution. The reaction mixture was stirred at 333 K for 50 min, and epichlorohydrin (9.63 mL, 0.12 mol) was added slowly. The reaction mixture was kept at 353 K for1 h; then 50% aqueous tetramethylammonium chloride (TMAC, 0.25 g, 0.00, 228 mol) and 3.65 g (0.091 mol) sodium hydroxide were added slowly in portions within 10 min. After addition, the temperature was maintained at 348-353 K and 12 mL distilled water was added, stirred and heated to separate out organic layers, which was washed with brine, separated and concentrated to get TGAE as a viscous brown liquid. 4-(2-(4-(bis(oxiran-2-ylmethyl)amino)phenoxy)ethoxy)-N,Nbis(oxiran-2-ylmethyl) benzenamine TGAE Colour, dark brown viscous liquid, EEW 170.8 g eq-1, Yield, 80%. FTIR (upsilon cm-1): 905 (C-O-C epoxide, asym), 810 (C-O-C epoxide, sym), 1223, 1067 (C-O, alkyl phenyl alcohol), 1375 (C-N ter. amine), 1507, 1456 (C=C aromatic), 2918 (C-H aliphatic), 1H NMR (300 MHz, CDCl3-d3): delta(ppm) = 2.8 (4H, m, 1a), 2.6 (4H, m, 1b), 3.2 (4H, m, 2), 3.7 (4H, m, 3a), 3.4 (4H, m, 3b), 6.8 (4H, dd, J = 9.3, 3.0 Hz, 4), 6.9 (4H, dd, J = 9.3, 2.4 Hz, 5) and 4.25 (4H, s,8). 13C NMR (300 MHz, CDCl3-d3): delta(ppm) = 45.37 (1), 47.18 (2), 50.74 (3), 114.8 (4), 116.4 (5), 151.3 (6), 143.4(7) and 67.4 (8).

At the same time, in my other blogs, there are other synthetic methods of this type of compound, 4,4′-(Ethane-1,2-diylbis(oxy))dianiline, and friends who are interested can also refer to it.

Reference:
Article; Siddiqi, Humaira Masood; Siraj, Amna; Khalid, Naila; Akhtar, Zareen; Zia Ul Haq, Muhammad; Journal of Thermal Analysis and Calorimetry; vol. 132; 1; (2018); p. 205 – 214;,
Ether – Wikipedia,
Ether | (C2H5)2O – PubChem

Reference of 104750-60-9, A common heterocyclic compound, 104750-60-9, name is 2-Bromo-1-(methoxymethoxy)-4-methylbenzene, molecular formula is C9H11BrO2, 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.

2-Bromo-1-(methoxymethoxy)-4-methylbenzene (2.3 g, 9.95 mmol) from Example I-122A was dissolved in tetrahydrofuran (39.8 mL), and Q-Phos (1,2,3,4,5-pentaphenyl-1′-(di-tert-butylphosphino)ferrocene) (0.141 g, 0.199 mmol) and bis(dibenzylideneacetone)palladium (0.114 g, 0.199 mmol) were added. The reaction was sparged with nitrogen 10 minutes. A solution of freshly-prepared (1-(methoxycarbonyl)cyclopropyl)zinc(II) bromide (45.2 mL, 19.91 mmol) in tetrahydrofuran was added dropwise. The reaction mixture was stirred at 50 C. for 30 minutes and at 45 C. for 15 hours. The reaction was cooled to ambient temperature and quenched with saturated aqueous ammonium chloride (40 mL). The mixture was diluted with methyl tert-butyl ether. The aqueous layer was extracted once with methyl tert-butyl ether. The combined organic layers were washed with brine, dried over sodium sulfate, filtered and concentrated. The crude material was purified by flash column chromatography, eluting with 0-20% ethyl acetate/heptanes to provide the title compound. 1H NMR (501 MHz, chloroform-d) delta ppm 7.06-6.99 (m, 2H), 6.97 (d, J=8.1 Hz, 1H), 5.16 (s, 2H), 3.60 (s, 3H), 3.45 (s, 3H), 2.28 (s, 3H), 1.63-1.57 (m, 2H), 1.12 (q, J=4.1 Hz, 2H)+

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; AbbVie S.a.r.l.; Galapagos NV; Altenbach, Robert J.; Bogdan, Andrew; Couty, Sylvain; Desroy, Nicolas; Gfesser, Gregory A.; Housseman, Christopher Gaetan; Kym, Philip R.; Liu, Bo; Mai, Thi Thu Trang; Malagu, Karine Fabienne; Merayo Merayo, Nuria; Picolet, Olivier Laurent; Pizzonero, Mathieu Rafael; Searle, Xenia B.; Van der Plas, Steven Emiel; Wang, Xueqing; Yeung, Ming C.; (189 pag.)US2019/77784; (2019); A1;,
Ether – Wikipedia,
Ether | (C2H5)2O – PubChem

Adding a certain compound to certain chemical reactions, such as: 954235-78-0, name is 4-Bromo-2-(difluoromethoxy)-1-fluorobenzene, 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 954235-78-0, Recommanded Product: 954235-78-0

A 40-mL vial containing 4-bromo-2-(difluoromethoxy)-1-fluorobenzene (1.00 g, 4.15 mmol) (purchased from Combi-Blocks, Inc.), 1,1′-bis(diphenylphosphino)ferrocene palladium(II)dichloride dichloromethane adduct (0.169 g, 0.207 mmol), bis(pinacolato)diboron (1.159 g, 4.56 mmol), and potassium acetate (1.222 g, 12.45 mmol) was flushed with N2 and subsequently charged with dioxane (4 mL). The slurry was stirred at 90 C. for 3.5 h. After cooling to rt, the reaction was quenched with H2O and extracted thrice with EtOAc. The organic extracts were combined, washed with brine, dried over Na2SO4, filtered, and concentrated in vacuo to a black oil. Column chromatography (25 g Snap Ultra column, 0% to 100% EtOAc/hept) afforded 2-(3-(difluoromethoxy)-4-fluorophenyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane (178 mg, 0.618 mmol, 14.89% yield) as a brown-black oil. m/z (ESI) 289.2 (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, 4-Bromo-2-(difluoromethoxy)-1-fluorobenzene, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; Amgen Inc.; Weiss, Matthew; Boezio, Alessandro; Boezio, Christiane; Butler, John R.; Chu-Moyer, Margaret Yuhua; Dimauro, Erin F.; Dineen, Thomas; Graceffa, Russell; Guzman-Perez, Angel; Huang, Hongbing; Kreiman, Charles; La, Daniel; Marx, Isaac E.; Milgrim, Benjamin Charles; Nguyen, Hanh Nho; Peterson, Emily; Romero, Karina; Sparling, Brian; US9212182; (2015); B2;,
Ether – Wikipedia,
Ether | (C2H5)2O – PubChem

Electric Literature of 121588-79-2, 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. 121588-79-2, name is trans-4-Methoxycyclohexanamine, This compound has unique chemical properties. The synthetic route is as follows.

4-(4-fluoro-3-nitrophenyl)-3,5-dimethylisoxazole (0.609 g, 2.58 mmol) was dissolved in dry THF (20ml) and TEA (1.079 ml, 7.74 mmol). (lr,4r)-4-methoxycyclohexanamine (0.4 g, 3.10 mmol) was added and the reaction warmed to 60C and left to stir at rt for 84h. After cooling to rt the reaction mixture was poured into ice water (100ml), then extracted with ethyl acetate (2 x 100ml). Combined organics were concentrated in vacuo (azeotroping with acetonitrile) to afford the crude 4-(3,5-dimethylisoxazol-4-yl)- N-((lr,4r)-4-methoxycyclohexyl)-2-nitroaniline (1.1 g, 3.12 mmol, >100%), which was used without purification in the next step; Rt 2.40 min (method 1); m/z 346 (M+H)+

The chemical industry reduces the impact on the environment during synthesis trans-4-Methoxycyclohexanamine. I believe this compound will play a more active role in future production and life.

Reference:
Patent; CELLCENTRIC LTD; PEGG, Neil Anthony; ONIONS, Stuart Thomas; TADDEI, David Michel Adrien; SHANNON, Jonathan; PAOLETTA, Silvia; BROWN, Richard James; SMYTH, Don; HARBOTTLE, Gareth; (376 pag.)WO2018/73586; (2018); A1;,
Ether – Wikipedia,
Ether | (C2H5)2O – PubChem

Reference of 2338-54-7,Some common heterocyclic compound, 2338-54-7, name is 4-Fluoro-3-methylanisole, molecular formula is C8H9FO, 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 l-fluoro-4-methoxy-2-methylbenzene (2.0 g, 14.29 mmol) in CC , NBS (2.55 g, 14.29 mmol) and PI1CO3H (80 mg) were added. The reaction mixture was heated at reflux for 2 h, cooled to room temperature, and the solid was filtered off. The filtrate was concentrated, and the residue was purified by silica gel column chromatography (eluting with PE/EA = 20/1) to give the target compound (3.0 g) as an oil. 1H NMR (CDC13): delta 6.97-6.83 (m, 3H), 4.48 (s, 2H), 3.78 (s, 3H).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 4-Fluoro-3-methylanisole, its application will become more common.

Reference:
Patent; ARAGON PHARMACEUTICALS, INC.; KAHRAMAN, Mehmet; GOVEK, Steven, P.; NAGASAWA, Johnny, Y.; SMITH, Nicholas, D.; WO2011/156518; (2011); A2;,
Ether – Wikipedia,
Ether | (C2H5)2O – PubChem