Category: ethers-buliding-blocks

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. 54314-84-0, name is ((3-Bromopropoxy)methyl)benzene, A new synthetic method of this compound is introduced below., COA of Formula: C10H13BrO

[(3-Benzyloxy-propyl)-ethoxy-phosphinoylmethyl]-phosphonic acid diethyl ester To an oven-dried flask was added 10.25 g (44.7 mmol) of (3-Bromo-propoxymethyl)-benzene and 7.67 mL (44.7 mmol) of triethyl phosphite. The flask was fitted with a short-path distillation head, for removal of bromoethane, and the mixture heated at 150¡ã C. for 4 h. The reaction was cooled to ambient temperature, and then diluted with 120 mL of absolute ethanol and 1.8 N KOH (120 mL, 216 mol). The distillation head was replaced with a reflux condenser and the solution heated at reflux for 5 h. The reaction was cooled then concentrated in vacuo. The basic aqueous layer was extracted with EtOAc (2*) and then acidified to pH 3 with conc. HCl. The aqueous layer was extracted with EtOAc (3*) and the combined extracts were dried over MgSO4 and concentrated. The resulting crude product (8.24 g) was used as is in the next reaction. 31P NMR (300 MHz, DMSO-d6) delta34.113.

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; Metcalf III, Chester A.; Shakespeare, William C.; Sawyer, Tomi K.; Wang, Yihan; Bohacek, Regine; US2003/114486; (2003); A1;,
Ether – Wikipedia,
Ether | (C2H5)2O – PubChem

Adding a certain compound to certain chemical reactions, such as: 1462-37-9, name is ((2-Bromoethoxy)methyl)benzene, 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 1462-37-9, Formula: C9H11BrO

Methyl 1-(2-(benzyloxy)ethyl)-3-cyclohexyl-1H-indole-6-carboxylate. Intermediate 4 (1.029 g, 4.0 mmol) was added to a suspension of NaH (192 mg of 60percent dispersion in mineral oil, 4.8 mmol) in DMF (5 mL). The reaction mixture was stirred at room temperature for 15 minutes, treated with benzyl 2-bromoethyl ether (0.7 mL, 4.4 mmol), stirred at room temperature for 2 hours, quenched with water, and extracted with ethyl acetate (2.x.50 mL). The organic layers were combined and washed (1N HCl), dried (MgSO4), filtered, and concentrated. The residue was purified by flash column chromatography (silica gel, 3:1 hexanes/ethyl acetate) to provide the desired product as a colorless thick oil (1.19 g, 76percent yield). MS m/z 392(MH+); 1H NMR (500 MHz, CDCl3) delta 1.31 (m, 1H), 1.45 (m, 4H), 1.80 (d, J=13.12 Hz, 1H), 1.87 (m, 2H), 2.10 (m, 2H), 2.84 (m, 1H), 3.79 (t, J=5.34 Hz, 2H), 3.94 (s, 3H), 4.33 (t, J=5.49 Hz, 2H), 4.45 (s, 2H), 7.12 (s, 1H), 7.20 (m, 2H), 7.27 (m, 3H), 7.66 (d, J=8.55 Hz, 1H), 7.78 (d, J=8.55 Hz, 1H), 8.08 (s, 1H).

At the same time, in my other blogs, there are other synthetic methods of this type of compound, ((2-Bromoethoxy)methyl)benzene, and friends who are interested can also refer to it.

Reference:
Patent; Hudyma, Thomas W.; Zheng, Xiaofan; He, Feng; Ding, Min; Bergstrom, Carl P.; Hewawasam, Piyasena; Martin, Scott W.; Gentles, Robert G.; US2006/46983; (2006); A1;,
Ether – Wikipedia,
Ether | (C2H5)2O – PubChem

Reference of 19056-40-7, 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. 19056-40-7, name is 4-Bromo-3-methoxyaniline, This compound has unique chemical properties. The synthetic route is as follows.

b 5-Amino-2-bromo-phenol A suspension of 4-bromo-3-methoxy-phenylamine (37.6 g, 0.186 mol) and tetrabutylammonium iodide (96 g, 0.260 mol) in dichloromethane (1.2 L) was cooled down to -78 C. A 1M solution of boron trichloride in dichloromethane (520 mL, 0.521 mol) was added dropwise, within 20 min. The cooling bath was removed. After 3 hours, the reaction mixture was poured onto ice water (4.5 kg). The organic layer was extracted with water. The combined aqueous layers were washed with dichloromethane. The pH was adjusted to 9 using sodium hydrogencarbonate. Sodium chloride was added until saturation. The aqueous layer was extracted with ethyl acetate. The combined organic layers were dried over sodium sulfate, filtered and the solvents were evaporated. The solid was washed with dichloromethane and dried under vacuum. 35.2 g of the title compound were obtained. Brown solid, ISP-MS: m/e=189.1 ([M+H]+).

The chemical industry reduces the impact on the environment during synthesis 4-Bromo-3-methoxyaniline. I believe this compound will play a more active role in future production and life.

Reference:
Patent; Klug, Michael G.; Mattei, Patrizio; Mueller, Werner; Neidhart, Werner; Nettekoven, Matthias Heinrich; Pflieger, Philippe; Plancher, Jean-Marc; US2003/158179; (2003); A1;,
Ether – Wikipedia,
Ether | (C2H5)2O – PubChem

Reference of 458-50-4, 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 458-50-4 as follows.

To a dry and N2 flashed flask was added 4-bromo-3-fluoroanisole (1.04 g, 5.07 mmol) in THF (6 mL) under N2. This was cooled to -78 ¡ãC, and n-BnLi (1.72 mL, 4.29 mmol) was added. The reaction was stirred at -78 ¡ãC for 30 min. The mixture above was added via cannula to a stirred solution of methyl 3-oxocyclobutane carboxylate (500 mg, 3.90 mmol) in dry Et20 (35 mL) at – 78 ¡ãC under N2. The reaction mixture was allowed to warm to room temperature and was stirred for 1 h. Satd aq. NH4C1 was added and the mixture was stirred until a clear solution resulted. This mixture was extracted with Et20 (3 x). The combined extracts were dried (MgS04) and concentrated in vacuo to give the crude product, which was purified by flash chromatography (Biotage Horizon, 40M, Si, -30 mL/min, 100percent hexanes for 260 mL, gradient to 40percent EtOAc in hexanes over 5184 mL) to afford methyl 3-(2-fluoro-4-methoxyphenyl)-3- hydroxycyclobutanecarboxylate (450 mg, 45 percent). NMR (500 MHz, CDC13): delta 7.32 (t, J= 8.9 Hz, 1 H); 6.69-6.63 (m, 2 H); 3.80 (s, 3 H); 3.74 (s, 3 H); 3.40 (s, 1 H); 3.03-2.93 (m, 2 H); 2.90-2.82 (m, 1 H); 2.67-2.61 (m, 2 H).

According to the analysis of related databases, 458-50-4, the application of this compound in the production field has become more and more popular.

Reference:
Patent; MERCK SHARP & DOHME CORP.; LU, Zhijian; CHEN, Yi-Heng; SMITH, Cameron; LI, Hong; THOMPSON, Christopher, F.; SWEIS, Ramzi; SINCLAIR, Peter; KALLASHI, Florida; HUNT, Julianne; ADAMSON, Samantha, E.; DONG, Guizhen; ONDEYKA, Debra, L.; QIAN, Xiaoxia; SUN, Wanying; VACHAL, Petr; ZHAO, Kake; WO2012/58187; (2012); A1;,
Ether – Wikipedia,
Ether | (C2H5)2O – PubChem

Reference of 103291-07-2, A common heterocyclic compound, 103291-07-2, name is 4-Bromo-1-fluoro-2-methoxybenzene, molecular formula is C7H6BrFO, 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.

Add sodium hydride (2.77 g, 60% w/w, 69.2 mmol) to a solution of 3-hydroxy- azetidine-1-carboxylic acid tert-butyl ester (10.9 g, 62.9 mmol) in dimethyl sulfoxide (100 mL). Stir the mixture for 30 min and then add 3-bromo-6-fluoroanisole (15.5 g, 75.5 mmol). Heat the mixture to 65 0C overnight. Cool the mixture to room temperature and then dilute the solution with saturated ammonium chloride and brine and extract with ethyl acetate. Wash the organics five times with brine, then dry over sodium sulfate and filter. Concentrate and purify via silica gel chromatography using a 0-45% gradient of ethyl acetate/hexane to give 10.4 g (46%) of the title compound as a clear oil.

The synthetic route of 103291-07-2 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; ELI LILLY AND COMPANY; WO2008/76562; (2008); A1;,
Ether – Wikipedia,
Ether | (C2H5)2O – PubChem

Synthetic Route of 41789-95-1, These common heterocyclic compound, 41789-95-1, name is 1-(3-Methoxyphenyl)-N-methylmethanamine, 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.

Example 8; 3-amino-4-(2,4-dichlorophenyl)-N-(3-methoxybenzyl)-N-methylpyrrolidine-1-carboxamide A solution of 1-benzyl-3-(2,4-dichlorophenyl)-4-nitropyrrolidine (1.5 g, 4.3 mmol) in dry CH2Cl2 (5 mL) was cooled to 0 C. and triphosgene (500 mg, 1.7 mmol) in CH2Cl2 was added over the course of 30 minutes. The reaction was quenched with H2O and extracted with CH2Cl2. The organics were then washed with saturated aqueous NaHCO3, dried, filtered and concentrated under reduced pressure. The crude material was divided into 10 portions (0.43 mmol each), and (3-methoxy-benzyl)methyl-amine (45 mg, 0.30 mmol), Et3N (30 mg, 0.30 mmol) and CH2Cl2 (1 mL) were added to a single portion. The solution was stirred for 4 hours and concentrated under reduced pressure. The unpurified material was taken up in 1:1 MeOH/AcOH (2 ml) and zinc dust (200 mg, 3 mmol) was added. After stirring 4 hours, the solution was carefully quenched with saturated aqueous NaHCO3 and extracted with several portions of EtOAc. The organics were combined, concentrated under reduced pressure and purified employing reverse phase chromatography (samples were purified by preparative HPLC on a Waters Symmetry C8 column (25 mm¡Á100 mm, 7 um particle size) using a gradient of 10% to 100% acetonitrile: 0.1% aqueous TFA over 8 minutes (10 minutes run time) at a flow rate of 40 mL/minutes) to provide the title compound. 1H NMR (300 MHz, d6-DMSO) delta ppm 7.60-7.61 (m, 1H), 7.39-7.43 (m, 2H), 7.24-7.27 (m, 1H), 6.82-6.85 (m, 3H), 4.30-4.34 (m, 2H), 3.73-3.84 (m, 4H), 3.47-3.54 (m, 2H), 3.27-3.34 (m, 2H), 3.14-3.18 (m, 1H), 2.67-2.73 (s, 3H). MS (ESI+) m/z 408 (M+H)+

The synthetic route of 41789-95-1 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Backes, Bradley J.; Hamilton, Gregory L.; Kopecka, Hana A.; Lai, Chunqiu; Longenecker, Kenton L.; Madar, David J.; Pei, Zhonghua; Stewart, Kent D.; Von Geldern, Thomas W.; US2006/264433; (2006); A1;,
Ether – Wikipedia,
Ether | (C2H5)2O – PubChem

Electric Literature of 60792-79-2, As we all know, there are many different methods for the synthesis of a compound, and people can choose the synthesis method that suits their own laboratory according to the actual situation. 60792-79-2 name is 2,2′-Oxybis(ethylamine) dihydrochloride, This compound is widely used in many fields, so it is necessary to find a new synthetic route. The downstream synthesis method of this compound is introduced below.

N,N-(2,2′-oxybis(ethane-2.1-divfflbis(2,4,6-trimethylaniline) (Example 1 1) [0088] In a drybox, 2,4,6-trimethylbromobenzene (500.0 muL, 3.27 mmol), 2,2′- oxydiethylamine dihydrochloride (289.3 mg, 1.63 mmol), sodium terf-butoxide (706.5 mg, 7.35 mmol), 4.0 mL of dimethyoxyethane, and 10.0 mM Pd(OAc)2 / CyPF-r-Bu (81.8 muL, 8.18 x 10-4 mmol) were added to a 20 mL scintillation vial equipped with a magnetic stirbar and sealed with a cap containing a PTFE septum. The reaction was placed into a temperature controlled aluminum heating block and stirred at 100 0C for 6 h. After cooling to room temperature, the reaction mixture was partitioned between 100 mL H2O/Et2O (1 :1), the organic phase separated and dried over MgSO4, followed by the removal of all volatiles to afford 505 mg (91.0 %) of the title compound.[0089] 1H NuMR spectra were obtained at 400 MHz and recorded relative to residual protio solvent. 13C NuMR spectra were obtained at 101 MHz and recorded relative to the residual solvent resonance. The spectra recorded are as follows:Eta NuMR (CDC13, 400 MHz, 22 0C): delta 2.24 (s, 6H), 2.28 (s, 12H), 3.15 (t, J= 5.0 Hz, 4H), 3.49 (br s), 3.61 (t, J = 5.0 Hz, 4H), 6.84 (s, 4H). 13C NuMR (CDCI3, 101 MHz, 22 0C): delta 18.2, 20.5, 48.2, 70.4, 129.4, 129.8, 131.3, 143.1.

At the same time, in my other blogs, there are other synthetic methods of this type of compound, 2,2′-Oxybis(ethylamine) dihydrochloride, and friends who are interested can also refer to it.

Reference:
Patent; UNIVATION TECHNOLOGIES, LLC; JOHNS, Adam, M.; WO2010/53696; (2010); A2;,
Ether – Wikipedia,
Ether | (C2H5)2O – PubChem

Application of 29026-74-2, 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. 29026-74-2, name is 2-Isopropoxyaniline, This compound has unique chemical properties. The synthetic route is as follows.

EXAMPLE 242C 1-(2-isopropoxyphenyl)piperazine The product from Example 242B (3.5 g, 23.2 mmol) was added slowly to bis-2-chloroethylaime hydrochloride (4.96 g, 27.78 mmol) at room temperature and refluxed for 48 hours. The reaction was cooled to room temperature and sodium carbonate added (9 g) and refluxed for another 48 hours. The mixture was cooled to room temperature, filtered and the white solid partitioned between dichloromethane and 3N sodium hydroxide. The organic phase was dried over magnesium sulfate, filtered and concentrated under reduced pressure to afford 3.2 g (63%) pink oil. 1H NMR (300 MHz, CDCl3) delta1.4 (d, 6H, J=6 Hz), 1.5-1.6 (m, 4H), 2.45-2.65 (m, 4H), 3.43 (m, 1H), 6.6-6.8 (m, 2H), 6.81-6.91 (m, 2H); MS (DCI/NH3) m/e 221 (M+H)+.

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

Reference:
Patent; Bhatia, Pramila A.; Daanen, Jerome F.; Hakeem, Ahmed A.; Kolasa, Teodozyj; Matulenko, Mark A.; Mortell, Kathleen H.; Patel, Meena V.; Stewart, Andrew O.; Wang, Xueqing; Xia, Zhiren; Zhang, Henry Q.; US2004/29887; (2004); A1;,
Ether – Wikipedia,
Ether | (C2H5)2O – PubChem

Application of 13070-45-6, 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 13070-45-6 as follows.

General procedure: (S)-C10-BridgePHOS (2.0mg, 2.4mol%) and Pd(OCOCF3)2 (0.8mg, 2mol%) were placed into an oven dried flask under a nitrogen atmosphere, and degassed fresh dry acetone (2mL) was added. The mixture was stirred at room temperature for 1h. Then acetone was removed under vacuum and a solvent system of CH2Cl2/TFE (1/1, 1mL) was added to the mixture to afford the catalyst solution. The substrate 1 (0.15mmol) and additive (1equiv) were placed in a reaction tube under nitrogen and the above catalyst solution was added to the tube. The mixture was then degassed and transferred to a stainless steel autoclave in a glove box. After exchanging the gas three times, the hydrogenation was carried out at 35C under 60bar H2. After several hours, the reaction mixture was concentrated under reduced pressure. After alkalization with saturated NaHCO3, the percentage conversion of product was determined by 1H NMR analysis of the crude product. The organic residue was purified by flash chromatography with ethyl acetate/petrol ether (1:50) to give pure product 2. Enantiomeric excess was determined using a Daicel Chiralcel column with hexane/i-propyl alcohol as the eluant.

According to the analysis of related databases, 13070-45-6, the application of this compound in the production field has become more and more popular.

Reference:
Article; Li, Chao; Chen, Jianzhong; Fu, Guanghong; Liu, Delong; Liu, Yangang; Zhang, Wanbin; Tetrahedron; vol. 69; 33; (2013); p. 6839 – 6844;,
Ether – Wikipedia,
Ether | (C2H5)2O – PubChem

Synthetic Route of 24743-14-4, As we all know, there are many different methods for the synthesis of a compound, and people can choose the synthesis method that suits their own laboratory according to the actual situation. 24743-14-4 name is 3-(3-Methoxyphenyl)-1-propene, This compound is widely used in many fields, so it is necessary to find a new synthetic route. The downstream synthesis method of this compound is introduced below.

EXAMPLE 1; Typical procedure for the stoichiometric conversion of alkenes to alkylene carbonates using NBS and DBU[0054] NBS (266 mg, 1.5 mmol) was added to a vial comprising a magnetic stirrer, and partially dissolved using water (1 ml_). DBU (0.35 ml_, 2.4 mmol) was added to the mixture using a syringe, followed by the immediate addition of the alkene (1.5 mmol). The reaction mixture was not stirred until the onset of the reaction. The vial was then placed in a stainless steal autoclave (Parr reactor) which was pressurized with CO2 at an overall pressure of 250 psi. The reactor was not purged prior to pressurization. The reaction temperature was maintained at about 40 to about 6O0C (depending on the nature of the alkene) using a Parr temperature controller. After 2-6 hours of reaction time (depending on the nature of the alkene), the reactor was cooled to room temperature and depressurized. Ethyl acetate (1 ml_) was used to extract the organic material. Following purification by flash chromatography, the product was characterized by 1H and 13C NMR. [0055]

At the same time, in my other blogs, there are other synthetic methods of this type of compound, 3-(3-Methoxyphenyl)-1-propene, and friends who are interested can also refer to it.

Reference:
Patent; MCGILL UNIVERSITY; WO2008/34265; (2008); A1;,
Ether – Wikipedia,
Ether | (C2H5)2O – PubChem