Author: Jessica.F

Application of 295376-21-5, 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. 295376-21-5, name is 1-Bromo-2-fluoro-3-methoxybenzene belongs to ethers-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below.

At room temperature, add 20 mL of toluene, compound 3-2 (4.8 g, 23.18 mmoL),Tris (dibenzylideneacetone) dipalladium (0.28g, 0.31mmoL),Tris (o-methylphenyl) phosphorus (0.19g, 0.62mmoL), replaced with nitrogen three times,The temperature was raised to 60 to 70 C. Add the toluene solution of compound 2 in the three-necked bottle R1 dropwise,After the dropwise addition, keep it at 60 70 for 1h;The reaction solution was filtered through celite, and the filtrates were combined and washed with 20 mL of water.It was washed with saturated brine, dried over anhydrous sodium sulfate, and concentrated in vacuo to about 20 mL at 50 C, and cooled to 20-30 C. 160 mL of n-heptane was added dropwise to precipitate a solid, which was filtered to obtain a off-white solid, without further drying One-step synthesis

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, 1-Bromo-2-fluoro-3-methoxybenzene, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; Lizhu Group Xin Beijiang River Pharmaceutical Co., Ltd.; Wang Biao; Peng Murong; Huang Lixia; Chen Guo; Li Chengbo; Feng Qiqing; (16 pag.)CN110372608; (2019); A;,
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Adding a certain compound to certain chemical reactions, such as: 592-55-2, name is 1-Bromo-2-ethoxyethane, 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 592-55-2, category: ethers-buliding-blocks

General procedure: To a solution of 2 (0.28 g, 1.132 mmol) in DMF (5 mL) was added potassium carbonate (0.438 g, 3.17 mmol) and 1-bromobutane (0.340 ml, 3.17 mmol). The mixture was heated at 90 C for 4 h, then cooled to rt and aq. HCl (0.2 M, 50 mL) was added. The mixture was extracted with CH2Cl2 (3 x 5 mL) and the combined organic layers were dried over MgSO4. Solvents were removed under reduced pressure and the residue was purified by silica gel chromatography using hexane:EtOAc (2:1) as eluent to give 3a (0.33 g, 91% 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:
Article; Slavik, Roger; Herde, Adrienne Mueller; Bieri, Daniel; Weber, Markus; Schibli, Roger; Kraemer, Stefanie D.; Ametamey, Simon M.; Mu, Linjing; European Journal of Medicinal Chemistry; vol. 92; (2015); p. 554 – 564;,
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Electric Literature of 24599-58-4, 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. 24599-58-4 name is 2,5-Dimethoxytoluene, 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.

2,5-dimethoxy toluene 1 (9.0 g, 59.21 mmol) in diethyl ether (90 cm3) was added to a stirred solution of iodine monochloride (10.17 g, 62.65 mmol) in chloroform (30 cm) over 30 minutes. The mixture was stirred overnight before 10% sodium thiosulfate (150 cm3) was added. The organics were extracted with 2×75 cm3) of diethyl ether. The organics were combined, washed with saturated aqueous NaHCO3 (150 cm3), brine (100 cm3), dried (MgSO4) and dried under vacuum. The resultant solid was recrystallised from methanol to yield the title compound as red solid 2 (11.3 g, 69%). [0085] Rf 0.52 (SiO2, Hex 3:1 EtOAc). [0086] Mp 80-82 C. (Literature 81-82 C. (Reed et al., JACS, 120(38): 9729-9734, 1998) [0087] 1H NMR (400 MHz, CDCl3) 2.12 (3H, s, CH), 3.72 (3H, s, OCH), 3.75 (3H, s, OCH), 6.60 (1H, s, ArH), 7.10 (1H, s, ArH) ppm.

At the same time, in my other blogs, there are other synthetic methods of this type of compound, 2,5-Dimethoxytoluene, and friends who are interested can also refer to it.

Reference:
Patent; Onco-NX Limited; Mcgown, Alan; Hadfield, John; Butler, John; US2015/210639; (2015); A1;,
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Adding a certain compound to certain chemical reactions, such as: 36805-97-7, name is 1,1-Di-tert-butoxy-N,N-dimethylmethanamine, 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 36805-97-7, Recommanded Product: 36805-97-7

d) 2-Chloro-6-methoxymethyl-isonicotinic acid tert-butyl ester2-Chloro-6-methoxymethyl-isonicotinic acid (3.48 g, 15.5 mmol, 1 eq) is dissolved in toluene (60 ml) and heated to 80 0C. N,N-dimethylformamid-di-tertbutylacetal (7.53 ml, 31 mmol, 2 eq) is added in portions over 8 hours. The reaction mixture is then diluted with TBME and washed with aqueous sodium bicarbonate. The organic layer is dried with sodium sulfate, filtered and concentrated to give the product. MS (ES+): 258 = [M+H]+

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; NOVARTIS AG; NOVARTIS PHARMA GmbH; WO2008/9750; (2008); A2;,
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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. 592-55-2, name is 1-Bromo-2-ethoxyethane, A new synthetic method of this compound is introduced below., Safety of 1-Bromo-2-ethoxyethane

Take 30.0g of compound A and 19.6g of K2CO3,162mL of N, N-dimethylformamide in a reaction flask, stir,25.3g of 2-bromoethylethyl ether was added, the temperature was raised to 60 C, and the reaction was performed for 2h. The reaction solution was poured into 270 mL of water, stirred for 0.5 h, and the solid was precipitated and filtered. The obtained filter cake was slurried with 540 mL of water for 1 h, filtered, and the filter cake was slurried with 240 mL of n-heptane for 1 h. The product was filtered and dried at 60 C to obtain product B1 43.5 g, yield 93%, HPLC purity: 99.0%.

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; Sichuan Kelun Pharmaceutical Institute Co., Ltd.; Zha Zhongyun; Pan Junzhu; Cao Zhi; Liu Zhiqiang; Feng Liejiang; Wang Lichun; Wang Jingyi; (9 pag.)CN110396063; (2019); A;,
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Application of 41789-95-1,Some common heterocyclic compound, 41789-95-1, name is 1-(3-Methoxyphenyl)-N-methylmethanamine, 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.

General procedure: A mixture of Pd(OAc)2 (6.7 mg, 0.030 mmol, 10 mmol%), Cu(OAc)2 (54.45 mg, 0.30 mmol, 1 equiv.), 1a (32.1 mg, 0.30 mmol, 1equiv.), CsF (136.7 mg, 0.90 mmol, 3 equiv.) was dissolved in a solvent of acetonitrile (3 mL) followed by addition of 2a (179 mg,0.60 mmol, 2 equiv.). The reaction mixture was stirred at 120 C for 24 h and progress of the reaction was monitored continuously byTLC with ethyl acetate: hexane eluent system. Upon completion of reaction the mixture was cooled to room temperature, poured into brine, and extracted with EtOAc. The combined extracts were dried over MgSO4 and filtered through pad of Celite eluting with ethylacetate. The filtrate was concentrated under reduced pressure and was purified by column chromatography (EtOAc/hexane) on silicagel to afford the 5,6-dihydrophenanthridine 3a. Compound 1i was synthesized in accordance with reported literature [25]. Characterization data of compounds 3a, 3c, and 3e were found exactly similar as reported in the literature (References of above compounds are mentioned in Supplementary data).

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

Reference:
Article; Asamdi, Manjoorahmed; Chauhan, Prakashsingh M.; Patel, Janki J.; Chikhalia, Kishor H.; Tetrahedron; vol. 75; 25; (2019); p. 3485 – 3494;,
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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 38380-85-7 as follows. name: 1-Bromo-4-cyclopropoxybenzene

Step 1 : A solution of 1-bromo-4-cyclopropoxybenzene (900 mg, 4.22 mmol) in THF (20 mL, anhydrous) was added n-BuLi (2.5 M, 2.6 mL) at -78C and stirred at -78C for 2 hours under N2. Then, thereto was added dropwise DMF (926 mg, 12.66 mmol, anhydrous) at – 78C and it was stirred for 2 hours. The solution was quenched with NH4Cl (aq. 1 mL) at – 78C and stirred at 0C for 0.5 hour. The mixture was diluted with ethyl acetate (10 mL). The mixture was filtered and the filtrate was concentrated under vacuum. The residue was diluted with ethyl acetate (30 mL), washed with brine (3 * 15 mL). The organic layer was dried with anhydrous Na2S04, filtered and concentrated in vacuum to give 4- cyclopropoxybenzaldehyde (700 mg). LC-MS: tR = 0.800 min (method 2), m/z = 162.8 [M + H]+.

According to the analysis of related databases, 38380-85-7, the application of this compound in the production field has become more and more popular.

Reference:
Patent; H. LUNDBECK A/S; KEHLER, Jan; RASMUSSEN, Lars, Kyhn; LANGGARD, Morten; JESSING, Mikkel; VITAL, Paulo, Jorge, Vieira; JUHL, Karsten; (157 pag.)WO2018/78038; (2018); A1;,
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Related Products of 854391-95-0,Some common heterocyclic compound, 854391-95-0, name is Bis(4-methoxybenzyl)amine hydrochloride, molecular formula is C16H20ClNO2, 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.

Preparation of intermediate II-22; A mixture of 2-chloro-5-bromopyrimidine (1.0 g, 5.16 mmol), N-(4- methoxybenzyl)(4-methoxyphenyl)methanamine hydrochloride, (cas 854391-95- 0) (1.59 g, 5.418 mmol) and DIPEA (2.68 mL, 15.48 mmol) in dry dioxane (10 mL) was heated for 1 h at 160C under microwave irradiation. On cooling, the mixture was diluted with EtOAc (200 mL) and the organic phase was washed with saturated aqueous NaHC03 (50 mL), brine (50 mL), dried (MgS04) and the solvent removed in vacuo to give a residue that was purified by column chromatography (hexane/EtOAc mixtures -20:1 to 10:1- as eluent) to give desired product as a white solid (1.81 g, 85% yield).

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

Reference:
Patent; CENTRO NACIONAL DE INVESTIGACIONES ONCOLOGICAS (CNIO); PASTOR FERNANDEZ, Joaquin; MARTINEZ GONZALEZ, Sonia; ALVAREZ ESCOBAR, Rosa Maria; RODRIGUEZ HERGUETA, Antonio; MARTIN HERNANDO, Jose Ignacio; RAMOS LIMA, Francisco, Javier; WO2011/89400; (2011); A1;,
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These common heterocyclic compound, 111-95-5, name is Bis(2-methoxyethyl)amine, 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. Formula: C6H15NO2

A mixture of 3,6-diaminopyrazine-2,5-dicarboxylic acid (200 mg, 1.01 mmol), bis-2- (methoxyethyl) amine (372 mL, 335.5 mg, 2.52 mmol), HOBt-H20 (459 mg, 3.00 mmol), and EDC-HC1 (575 mg, 3.00 mmol) were stirred together in DMF (20 mL) for 1 h at room temperature. The mixture was concentrated to dryness and the residue was partitioned with EtOAc and water. The layers were separated and the EtOAc solution was washed with saturated NaHC03 and brine. The solution was dried over anhydrous Na2S04, filtered and concentrated. Purification by radial flash chromatography (Si02, 10/1 CHCb-MeOH) afforded 228.7 mg (53% yield) of Example 4 as an orange foam: lH NMR (300MHz, CDC1 ), delta 4.92 (s, 4 H), 3.76 (apparent t, J = 5.4 Hz, 4 H), 3.70 (apparent t, J = 5.6 Hz, 4 H), 3.64 (apparent t, J = 5.4 Hz, 4 H), 3.565 (apparent t, J = 5.4 Hz), 3.67 (s, 6 H), 3.28 (s, 6 H). 13C NMR (75 MHz, CDCL3)? 167.6 (s), 145.6 (s), 131.0 (s), 72.0 (t), 70.8 (t), 59.2 (q), 49.7 (t), 47.1 (t). LCMS (5-95% gradient acetonitrile in 0.1% TFA over 10 min), single peak retention time = 3.14 min on 30 mm column, (M+H)+ = 429. UV/vis (100 muMu in PBS) abs = 394 nm. Fluorescence (100 muiotaeta) lambda6Chi = 394 nm

The synthetic route of Bis(2-methoxyethyl)amine has been constantly updated, and we look forward to future research findings.

Reference:
Patent; MEDIBEACON INC.; DORSHOW, Richard, B.; ROGERS, Thomas, E.; (90 pag.)WO2016/183351; (2016); A1;,
Ether – Wikipedia,
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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. 22236-08-4, name is 3-(Difluoromethoxy)aniline, A new synthetic method of this compound is introduced below., SDS of cas: 22236-08-4

General procedure: A two neck round bottom flask under argon equipped with acondenser was charged with aldehyde 4 (1.0 equiv.) and 4-chloroaniline 3l (1.1 equiv.) in 2-pentanol [0.3 M] and stirred atreflux for 2 h. The tetronic acid 5 (1.1 equiv.) in 2-pentanol (minimumamount) was then added at reflux. After another 10 min atreflux, the third component aniline 3 (1.0 equiv.) was added neat.The reaction mixture was refluxed for an additional 30 min. Allvolatiles were evaporated under vacuum and the crude product purified by recrystallization in ethanol or by flash chromatographyon silica gel

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:
Article; Jeedimalla, Nagalakshmi; Flint, Madison; Smith, Lyndsay; Haces, Alberto; Minond, Dmitriy; Roche, Stephane P.; European Journal of Medicinal Chemistry; vol. 106; (2015); p. 167 – 179;,
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