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. 1836-62-0, name is 2-(2-Methoxyphenoxy)ethylamine, A new synthetic method of this compound is introduced below., Application In Synthesis of 2-(2-Methoxyphenoxy)ethylamine

2-(2-Methoxyphenoxy)ethyl amine (15.09 g), N,N-diisopropylethyl amine (10.8 g), 4-(oxiran-2yl-methoxy)-9H-carbazole (20.0 g) and monoglyme (30 mL) were heated to 80-850C. After 8-12 hours, the reaction mixture was cooled to room temperature and ethyl acetate (40 mL) was added. The contents were cooled to 0-50C. The solid is filtered after slurry in ethylacetate to get crude Carvedilol (100 mL). (Purity: 98.62%; Yield: 36.26 %; Bis-impurity: 0.65%.)

The synthetic route of 1836-62-0 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; INOGENT LABORATORIES PRIVATE LIMITED1; WO2009/157015; (2009); A2;,
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Ether | (C2H5)2O – PubChem

Reference of 2930-05-4, 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. 2930-05-4 name is 2-((Benzyloxy)methyl)oxirane, 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.

In a glass RBF equipped with a Teflon- coated magnetic stirrer and a reflux condenser was dissolved 2-benzyloxymethyl-oxirane (1 eq.) in a 3:1 (v/v) solution (0.08 M) of methanol and water. To this was then added sodium azide (2 eq.) and ammonium chloride (1.5 eq.), and the resulting mixture was heated at reflux for 14 h. The reaction solution was cooled to RT and diluted with tBuOMe. The organic layer was separated, washed further with sat. aq. NH4C1, dried over MgSO4, and filtered. Concentration of the filtrate in vacuo delivered the crude product as a pale yellow oil. Further purification by way of column chromatography (Si02, gradient elution, 9:1 (v/v) Hex: EtOAc – 3:7 (v/v) Hex:EtOAc) furnished the desired product as a colorless oil (71% yield).

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

Reference:
Patent; MERCK PATENT GMBH; JORAND-LEBRUN, Catherine; LAN, Ruoxi; CHEN, Austin; CLARK, Ryan C.; (268 pag.)WO2017/49068; (2017); A1;,
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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. 38336-04-8, name is 2-(Benzyloxy)-1-ethanamine, A new synthetic method of this compound is introduced below., Quality Control of 2-(Benzyloxy)-1-ethanamine

Example 25; 5-cvclopropyl-2-(4-fluorophenyl)-6-(N-((2-hvdroxy-1 ,2-oxaborolan-4- yl)methyl)methylsulfonamido)-N-(2-hvdroxyethyl)benzofuran-3-carboxamideStep 1: N-(2-(benzyloxy)ethyl)-5-cyclopropyl-2-(4-fluorophenyl)-6- (methylsulfonamido)benzofuran-3-carboxamide5-Cyclopropyl-2-(4-fluorophenyl)-6-(methylsulfonamido)benzofuran-3-carboxylic acid (1 .0 g, 2.568 mmol) was stirred in dry DMF (15 mL) at ambient temperature with DIPEA (0.730 g, 5.650 mmol) and HATU (1.71 g, 3.082 mmol). After stirring for 15 minutes, benzyloxymethanamine (1 .552 mg, 10.272 mmol) in 15 mL of THF was added. The reaction mixture was stirred for another 2 hours and diluted with EtOAc (30 mL) and water (30 mL). The organic layer was separated and the aqueous layer was extracted with EtOAc (30 mL x2). The combined organic layers were washed with brine (30 mL), dried over anhydrous Na2S04, filtered and concentrated in vacuo. The residue was purified by columnchromatography (eluting with 0-50% ethyl acetate in petroleum) to give N-(2- (benzyloxy)ethyl)-5-cyclopropyl-2-(4-fluorophenyl)-6-(methylsulfonamido)benzofuran-3- carboxamide (1.4 g, crude, 104% yield).

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; GLAXO GROUP LIMITED; JOHNS, Brian Alvin; SHOTWELL, John Brad; HAIGH, David; WO2012/67663; (2012); A1;,
Ether – Wikipedia,
Ether | (C2H5)2O – PubChem

Synthetic Route of 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.

Reference 2; Synthesis of 3-methoxy-4-(2-methylpyridin-4-yl)benzenamineStep l4-Bromo-3-methoxyaniline (3.70 g, 18.3 mmol; Aldrich) was dissolved in N,N- dimethylformamide (40 mL, 500 mmol) and triethylamine (2.68 mL, 19.2 mmol) was added. Acetic anhydride (1.81 mL, 19.2 mmol) was added and the reaction mixture stirred for 5 hours. The reaction mixture was diluted with water and extracted with diethyl ether. The organic layer was dried over Na2SO4, filtered and diluted with hexames. The layer was concentrated to minimal volume and the resultant slurry was filtered and washed with hexanes to yield N-(4- bromo-3-methoxyphenyl)acetamide as a light peach solids.

According to the analysis of related databases, 19056-40-7, the application of this compound in the production field has become more and more popular.

Reference:
Patent; AMGEN INC.; WO2009/75874; (2009); A1;,
Ether – Wikipedia,
Ether | (C2H5)2O – PubChem

Reference of 588-63-6,Some common heterocyclic compound, 588-63-6, name is (3-Bromopropoxy)benzene, molecular formula is C9H11BrO, 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.

[0187] Into a 5 L 3-necked roundbottom flask, was placed a solution of l-(3- bromopropoxy)benzene (250 g, 1.16 mol) in THF (600 ml). To this was added dimethylamine in water (1 L 33percent). To the mixture was added KOH (200 g, 4.46 mol). The resulting solution was allowed to react, with stirring, for 5 hours while the temperature was maintained at room temperature. The reaction progress was monitored by TLC (EtOAc/PE = 1 :3). The resulting solution was extracted five times with 200 ml of EtOAc and the organic layers combined. The filtrate was concentrated by evaporation under vacuum using a rotary evaporator. This resulted in 20Og of crude N,N-dimethyl-3-phenoxypropan-l -amine as light yellow oil.

The synthetic route of 588-63-6 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; KALYPSYS, INC.; WO2008/73733; (2008); A1;,
Ether – Wikipedia,
Ether | (C2H5)2O – PubChem

Application of 801282-00-8, These common heterocyclic compound, 801282-00-8, name is 2-Fluoro-3-methoxyaniline, 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.

[00385] Intermediate 30. l-(3-Chloro-2-fluorophenyl)-5-methoxy-lH-l,2,3-triazole-4- carboxylic acid: To a solution of 2-fluoro-3-methoxyaniline (1 g, 7.09 mmol) in TFA (10 mL) and water (5 mL) at 0 C was added an aq. solution of NaN02 (0.733 g, 10.63 mmol) dropwise. The resulting mixture was stirred at 0 C for 0.5 h and NaN3 (0.921 g, 14.17 mmol) was added portionwise. The reaction mixture was gradually warmed to rt and stirred for 4 h. The reaction was quenched with water (150 mL) and extracted with EtOAc (2×100 mL). The organic layer was washed with sodium phosphate solution (10%) and brine (50 mL), dried, and concentrated. The resulting brown oil was re- dissolved in DMSO (20 mL) and added t-butylpropiolate (1 mL) followed by K2CO3 (1 g), Cu(OAc)2 (0.2 g), and sodium ascorbate (100 mg). The resulting mixture was stirred at rt overnight. The reaction was quenched with water (200 mL) and extracted with EtOAc (2 x 100 mL). The organic layer was dried and concentrated. The residue was purified by silica gel chromatography to yield the desired product as brown oil. 1H NMR (400 MHz, CDCI3) delta 13.19 (br. s., 1H), 7.36 – 7.20 (m, 2H), 7.17 – 6.95 (m, 1H), 6.76 (td, J = 8.1, 1.3 Hz, 1H), 3.91 (s, 3H), 1.74 – 1.49 (m, 10H). MS(ESI) m/z: 238.0 (M+H)+.

The synthetic route of 801282-00-8 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; BRISTOL-MYERS SQUIBB COMPANY; PINTO, Donald J.; CORTE, James R.; GILLIGAN, Paul J.; FANG, Tianan; SMITH II, Leon M.; WANG, Yufeng; YANG, Wu; EWING, William R.; WO2013/22818; (2013); A1;,
Ether – Wikipedia,
Ether | (C2H5)2O – PubChem

Reference of 54149-17-6,Some common heterocyclic compound, 54149-17-6, name is 1-Bromo-2-(2-methoxyethoxy)ethane, molecular formula is C5H11BrO2, 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.

3-(2-(2-Methoxyethoxy)ethoxy)prop-1-yne (9) To a stirred suspension of sodium hydride (3.12 g, 78.0 mmol) in THF (100 mL) cooled to 5 C. in an ice-bath was added a solution of propargyl alcohol (4.60 g, 78.0 mmol) in THF (20 mL) drop-wise. The mixture was stirred at 5 C. for 30 min and was then allowed to warm to RT and treated dropwise with 1-bromo-2-(2-methoxyethoxy)ethane (7.00 mL, 52.0 mmol). The reaction mixture was stirred at RT for 16 hr and was then, diluted with water (100 mL) and extracted with diethyl ether (2*100 mL). The combined organic extracts were dried, filtered and evaporated in vacuo. The residue was purified by flash column chromatography, eluting with 30% EtOAc in heptane, to afford the title compound (9) (250 mg, 9%) as a colourless oil: 1H NMR (500 MHz, MeOD) delta: 4.18 (2H, d), 3.66-3.69 (2H, m), 3.60-3.66 (4H, m), 3.52-3.56 (2H, m), 3.36 (3H, s), 2.84 (1H, t).

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-2-(2-methoxyethoxy)ethane, its application will become more common.

Reference:
Patent; King-Underwood, John; Ito, Kazuhlro; Murray, Peter John; Hardy, George; Brookfield, Frederick Arthur; Brown, Christopher John; US2012/208799; (2012); A1;,
Ether – Wikipedia,
Ether | (C2H5)2O – PubChem

Synthetic Route of 101-55-3,Some common heterocyclic compound, 101-55-3, name is 1-Bromo-4-phenoxybenzene, molecular formula is C12H9BrO, 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.

The (S) -A40.2g (0.64mmol), 4- phenoxy-bromobenzene 0.24g (0.96mmol, 1.5eq.), Palladium acetate 0.013g (0.06mmol, 0.1eq.), BINAP0.037g (0.06mmol after, 0.1eq.), cesium carbonate 0.52g (1.6mmol, 2.5eq.) swap argon, DMF (4mL), the reaction 100 8 h, concentrated after adding saturated brine, extracted with methylene chloride and dried, Biotage silica gel column chromatography (petroleum ether / ethyl acetate = 28%) to give a pale yellow solid A70.27g, yield 87%.

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-4-phenoxybenzene, its application will become more common.

Reference:
Patent; Nanjing Yong Shan Biological Technology Co., Ltd.; Wang Yazhou; Jin Qiu; Tang Feng; Huang Wei; Hua Yulin; (10 pag.)CN103113375; (2017); B;,
Ether – Wikipedia,
Ether | (C2H5)2O – PubChem

Related Products of 171290-52-1, These common heterocyclic compound, 171290-52-1, name is 3,5-Dimethoxyphenylacetylene, 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 methoxy ethynylbenzenes (20 mmol) and methoxy substituted aryl iodide (22 mmol) in isopropylamine (120 ml) were added Pd(PPH3)2Cl2 (0.2 mmol) and CuI (0.4 mmol). The reaction mixture was stirred at ambient temperature for 6 hours under a slow stream of nitrogen. The reaction mixture was filtered and the residues were washed with ethyl acetate and the solvent evaporated from the combined filtrates. The crude product was purified by column chromatography on silica gel using petroleum ether/ethyl acetate (9:1) as an eluent to give methoxytolans.

Statistics shows that 3,5-Dimethoxyphenylacetylene is playing an increasingly important role. we look forward to future research findings about 171290-52-1.

Reference:
Patent; KENT STATE UNIVERSITY; SUMMA HEALTH SYSTEM; WO2008/157745; (2008); A1;,
Ether – Wikipedia,
Ether | (C2H5)2O – PubChem

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. 450-88-4, name is 1-Bromo-4-fluoro-2-methoxybenzene belongs to ethers-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below. Recommanded Product: 1-Bromo-4-fluoro-2-methoxybenzene

A mixture of 1 -bromo-4-fluoro-2-methoxybenzene (CAS No. [450-88-4]; 10.0 g, 48.8 mmol) in concentrated sulfuric acid (50 ml.) was cooled to 0 C and treated dropwise with a freshly prepared mixture of fuming nitric acid (1.05 eq., 2.1 ml_, 51 mmol) and concentrated sulfuric acid (1.85 eq., 4.8 ml_, 90 mmol). The reaction mixture was stirred at 0 C for 30 minutes and poured in small portions on ice water. The formed precipitate was filtered off, washed with cold water and kept. The filtrate was extracted with ethyl acetate and the organic layer combined with the isolated precipitation. The organic layer was dried with sodium sulfate and concentrated in vacuo. The obtained material was purified by flash chromatography (Si02-hexane/ ethyl acetate) to give the title compound (5.88 g, 44%). 1H-NM (400MHz, DMSO-de): delta [ppm] = 4.00 (s, 3H), 7.44 (d, 1 H), 8.40 (d, 1 H).UPLC- UPLC-MS (ESI-): [M – H]” = 248/250; Rt = 1.17 min (Br isotope pattern; Method E).

The synthetic route of 450-88-4 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; BAYER PHARMA AKTIENGESELLSCHAFT; PANKNIN, Olaf; ZIMMERMANN, Katja; NEUHAUS, Roland; (162 pag.)WO2017/5674; (2017); A1;,
Ether – Wikipedia,
Ether | (C2H5)2O – PubChem