Category: ethers-buliding-blocks

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 54149-17-6 as follows. 54149-17-6

Under an argon atmosphere, bisimine 11 (3.0 g, 10.12 mmol, 1 eq.), 1-bromo-2-(2-methoxyethoxy) ethane (3.35 mL, 22.26 mmol, 2.2 eq.) of and K2CO3 (5.59 g, 40.48 mmol, 4 eq.) were dissolved in 150 mL of dry DMF in a vacuum dried Schlenk flask. The contents were heated at 100C for 24 hours and the reaction was cooled to room temperature and 200 mL of distilled water was added to it. This was then extracted with EtOAc (3¡Á200 mL) and washed with distilled water (300 mL) and with brine (200 mL). The organic layers were combined and dried over anhydrous Na2SO4 and concentrated in vacuuo to yield a brownish-yellow coloured paste. This paste was thoroughly washed with pentane (3¡Á20 mL) and dried to a yellow powder.

According to the analysis of related databases, 54149-17-6, the application of this compound in the production field has become more and more popular.

Reference:
Article; Shahane, Saurabh; Toupet, Loic; Fischmeister, Cedric; Bruneau, Christian; European Journal of Inorganic Chemistry; 1; (2013); p. 54 – 60;,
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A common compound: 115144-40-6, name is 3,4-Difluoroanisole, belongs to ethers-buliding-blocks compound, it can change the direction of chemical reaction, and react with certain compounds to generate new functional products. A new synthetic method of this compound is introduced below. 115144-40-6

a) 7.29 ml (66.3 mmol) of titanium tetrachloride were added while stirring to a solution, cooled to 0, of 5.73 g (39.8 mmol) of 3,4-difluoroanisole in 30 ml of anhydrous dichloromethane. Subsequently, the mixture was treated dropwise over 10 minutes with 3.51 ml (39.6 mmol) of 1,1-dichloromethyl methyl ketone and stirred at room temperature for one hour. The mixture was poured into 100 ml of ice-water, extracted twice with 150 ml of dichloromethane each time and the combined organic phases were washed once with 100 ml of water and once with 100 ml of saturated sodium chloride solution. After drying over magnesium sulfate concentration was carried out in a vacuum. The crude product obtained was purified by column chromatography on silica gel (hexane/ethyl acetate 4:1). There were obtained 5.8 g (84%) of 4,5-difluoro-2-methoxybenzaldehyde as a white solid with m.p. 74.

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, 115144-40-6, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; Hoffmann-La Roche Inc.; US5955495; (1999); A;,
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Adding a certain compound to certain chemical reactions, such as: 103291-07-2, name is 4-Bromo-1-fluoro-2-methoxybenzene, 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 103291-07-2, 103291-07-2

To a solution of 69A (2.7 g, 13.1 mmol) in THF (25 mL) at -78 C. was added n-BuLi (1.6 M in hexanes, 11.0 mL, 17.7 mmol). The mixture was stirred at -78 C. for 40 min before trimethyl borate (2.7 mL, 24.3 mmol) was added. The reaction was left stirring from -78 C. to rt over 18 h. It was quenched with 1.0 N HCl (40 mL), extracted with EtOAc, washed with brine and dried over Na2SO4. After evaporation of the solvent, the crude solid product was triturated with EtOAc/hexanes (1:4). After filtration, 69B (0.75 g, 35% yield) was collected as a white solid. 1H NMR (400 MHz, Methanol-d4) delta ppm 3.86 (s, 3 H) 7.03-7.45 (m, 3 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-1-fluoro-2-methoxybenzene, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; Bristol-Myers Squibb Company; US2007/3539; (2007); A1;,
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The chemical industry reduces the impact on the environment during synthesis 1535-73-5, name is 3-Trifluoromethoxyaniline, I believe this compound will play a more active role in future production and life. 1535-73-5

Example 61 : 6-(6-Amino-pyrimidin-4-ylsulfanyl)-naphthalene-1-carboxylic acid (3- trifluoromethoxy-phenvP-amide; To 95 mg (0.32 mMol) 6-(amino-pyrimidin-4-ylsulfanyl)-naphthalene-1-carboxylic acid, 85 mg(0.48 mMol) 3-trifluoromethoxy-aniline, 446 mul (3.2 mMol) Et3N and 4 mg (0.03 mMol) DMAP EPO in 3 ml DMF, 0.37 ml (0.63 mMol) propylphosphonic anhydride are added. After 3 h at rt, the reaction mixture is worked up as described for Ex. 58, yielding the title compound: m.p.: 197- 199 ¡ãC; MS: [M+1]+ = 457.

The chemical industry reduces the impact on the environment during synthesis 1535-73-5. I believe this compound will play a more active role in future production and life.

Reference:
Patent; NOVARTIS AG; NOVARTIS PHARMA GMBH; WO2006/59234; (2006); A2;,
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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 111-95-5 as follows. 111-95-5

Bis(2-methoxyethyl)amine (9.0 mL, 60.8 mmol, 1.8 eq.) was added dropwise to a solutionof PCl3 (3.0 mL, 34.3 mmol) in dry hexane (90 mL) under N2 at 0 C. The resulting white slurrywas stirred at 20 C for 1 h, filtered and washed with hexanes (3x 100 mL). The solvent wasremoved (rotavap) and the residue distilled under reduced pressure (125 C, 100 mmHg). Theproduct was isolated as a colorless clear liquid (5.14 g, 64%).Data for 29a:1H-NMR: (500 MHz, CDCl3)delta 3.33 (s, 6 H, OCH3), 3.49 (s, 8 H, 1-H, 2-H).13C-NMR: (125 MHz, CDCl3)delta 48.6 (d, J = 16.8 Hz), 58.9, 71.1 (d, J = 2.6 Hz).31P NMR: (200 MHz, CDCl3)delta -84.2.

According to the analysis of related databases, 111-95-5, the application of this compound in the production field has become more and more popular.

Reference:
Article; Boese, Dietrich; Denmark, Scott E.; Synlett; vol. 29; 4; (2018); p. 433 – 439;,
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402-07-3, The chemical industry reduces the impact on the environment during synthesis 402-07-3, name is 4-Bromo-3-methoxybenzotrifluoride, I believe this compound will play a more active role in future production and life.

A vial was charged with 6-bromo-N-(4-methoxybenzyl)-N-(thiazol-2-yl)- 3,4-dihydro-2H-benzo[b][l,4]oxazine-7-sulfonamide (107.43 mg, 0.216 mmol), l-bromo-2-methoxy-4-(trifluoromethyl)benzene (Sigma-Aldrich, St. Loius, MO, 193 mg, 0.757 mmol), Xantphos (25.04 mg, 0.043 mmol), Pd2(dba)3 (19.82 mg, 0.022 mmol), and cesium carbonate (212 mg, 0.649 mmol). The vessel was flushed with Ar (g), then 1,4-dioxane (2164 mu) was added. The vessel was sealed and placed in a 100 C heating bath for 20 h. The mixture was cooled to room temperature, diluted with EtOAc, and filtered through celite. The filtrate was concentrated, and the residue was purified by chromatgraphy on silica gel (12-g Redi-Sep Gold column, 0-50% EtO Ac/Heptane) to give 6-bromo-4-(2-methoxy-4- (trifluoromethyl)phenyl)-N-(4-methoxybenzyl)-N-(thiazol-2-yl)-3,4-dihydro-2H- benzo[b][l,4]oxazine-7-sulfonamide (67 mg, 0.100 mmol, 46.2 % yield) as a yellow foam: m/z (ESI) 670.2 (M+H)+

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

Reference:
Patent; AMGEN INC.; BOEZIO, Christiane; BOEZIO, Alessandro; BREGMAN, Howard; CHAKKA, Nagasree; COATS, James R.; COPELAND, Katrina W.; DIMAURO, Erin F.; DINEEN, Thomas; GAO, Hua; LA, Daniel; MARX, Isaac E.; NGUYEN, Hanh Nho; PETERSON, Emily Anne; WEISS, Matthew; WO2013/122897; (2013); A1;,
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349-65-5, A common heterocyclic compound, 349-65-5, name is 2-Methoxy-5-(trifluoromethyl)aniline, molecular formula is C8H8F3NO, 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.

Synthesis of N-(2-Methoxy-5-(trifluoromethyl)phenyl)-N’-(4-(2-(N-methylcarbamoyl)-4-pyridyloxy)phenyl) Urea To a solution of 2-methoxy-5-(trifluoromethyl)aniline (0.15 g) in anh CH2Cl2 (15 mL) at 0 C. was added CDI (0.13 g). The resulting solution was allowed to warm to room temp. over 1 h, was stirred at room temp. for 16 h, then was treated with 4-(2-(N-methylcarbamoyl)-4-pyridyloxy)aniline (0.18 g). The resulting yellow solution was stirred at room temp. for 72 h, then was treated with H2O (125 mL). The resulting aqueous mixture was extracted with EtOAc (2*150 mL). The combined organics were washed with a saturated NaCl solution (100 mL), dried (MgSO4) and concentrated under reduced pressure. The residue was triturated (90% EtOAc/10% hexane). The resulting white solids were collected by filtration and washed with EtOAc. The filtrate was concentrated under reduced pressure and the residual oil purified by column chromatography (gradient from 33% EtOAc/67% hexane to 50% EtOAc/50% hexane to 100% EtOAc) to give N-(2-methoxy-5-(trifluoromethyl)phenyl)-N’-(4-(2-(N-methylcarbamoyl)-4-pyridyloxy)phenyl) urea as a light tan solid (0.098 g, 30%): TLC (100% EtOAc) Rf 0.62; 1H NMR (DMSO-d6) delta2.76 (d, J=4.8 Hz, 3H), 3.96 (s, 3H), 7.1-7.6 and 8.4-8.6 (m, 11H), 8.75 (d, J=4.8 Hz, 1H), 9.55 (s, 1H); FAB-MS m/z 461 ((M+H)+).

The synthetic route of 349-65-5 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; BAYER CORPORATION; US2003/144278; (2003); A1;,
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Some common heterocyclic compound, 54314-84-0, name is ((3-Bromopropoxy)methyl)benzene, molecular formula is C10H13BrO, 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. 54314-84-0

b 1-(3-Benzyloxy-propyl)-5-fluoro-indole-3-carboxylic acid To a solution of a) (0.86 g, 4.45 mmol) and benzyl 3-bromopropyl ether (0.78 mL, 4.45 mmol) in dry DMF (20 mL) was added potassium carbonate (2.46 g, 17.8 mmol), and the mixture was stirred under nitrogen at room temperature overnight. The mixture was partitioned between water and ethyl acetate and the organic phase was washed with water followed by brine and concentrated. The residue was dissolved in ethanol (15 mL) and sodium hydroxide in water (25percent, 50 mL) was added. The reaction mixture was heated at 90¡ã C. for 2 hours, cooled and washed with ethyl acetate. After acidification of the aqueous phase with hydrochloric acid, the product was extracted with ethyl acetate twice. The organic layers were washed with brine, dried and concentrated affording the sub-title product as an off-white solid (1.25 g, 86percent). 1H NMR (400 MHz, CDCl3): delta7.91 (1H, s); 7.87 (1H, dd); 7.36-7.25 (6H, m); 7.01 (1H, dt); 4.46 (2H, s); 4.30 (2H, t); 3.38 (2H); 2.15-2.11 (2H, m).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 54314-84-0, its application will become more common.

Reference:
Patent; Astrazeneca AB; US6492406; (2002); B1;,
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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. 4179-19-5, name is 3,5-Dimethoxytoluene, This compound has unique chemical properties. The synthetic route is as follows., 4179-19-5

1,3-dimethoxy-5-methylbenzene (30 g, 0.20 mol) and dichloromethane (900 mL) were added to a dry round bottom flask (1 L).To the above solution, a sulfone dichloride (52.5 g, 0.40 mol) was added dropwise under ice-cooling, and the mixture was stirred and stirred at room temperature overnight.After the reaction was completed, NaHCO3 aqueous solution was added dropwise to adjust pH=8, extracted with dichloromethane, washed with dilute hydrochloric acid and distilled water, and dried.Concentration under reduced pressure gave the compound 2,4-dichloro-1,5-dimethoxy-3-methylbenzene (31 g, white solid).

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; Rudong Lingda Bio-pharmaceutical Technology Co., Ltd.; Wang Hui; (20 pag.)CN110016026; (2019); 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. 2062-98-8, name is Perfluoro(2-methyl-3-oxahexanoyl) fluoride, A new synthetic method of this compound is introduced below., 2062-98-8

To the thus-obtained unpurified Compound A (3.86 g), were added 20 mL of tetrahydrofuran and 4.6 mL (57 mmol) of pyridine. Then, 15.1 g (45.6 mmol) of C3F7OCF(CF3)COF was added, dropwise, while keeping an internal temperature in the range of from 0 C. to 10 C. After completion of the dropwise addition, the internal temperature was elevated to a temperature in the range of from 20 C. to 30 C., and the reaction mixture was stirred for 1 hour. Then, 50 mL of a saturated sodium bicarbonate aqueous solution was added thereto, dropwise, and then 50 mL of ethyl acetate was added, followed by separation. Then, concentration of the resultant mixture was conducted, thereby to obtain 13.6 g (16.9 mmol, 89%) of Exemplified compound (I-6).The below-shown are identification data of the Exemplified compound (I-6).1H NMR (300 MHz, CDCl3): delta 1.18 to 1.31 (m, 9H), 3.90 to 4.09 (m, 2H), 4.14 to 4.49 (m, 4H), 4.78 to 4.90 (m, 1H)19F NMR (282.4 MHz, CDCl3): delta -131.85 (m, 2F), -129.75 (s, 2F), -86.64 (m, 2F), -86.11 (m, 2F), -82.17, -82.09 (s (doublet), 3F), -81.40 (s, 3F), -80.33 (m, 2F), -79.79 (m, 2F)

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; FUJIFILM Corporation; US7501545; (2009); B2;,
Ether – Wikipedia,
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