Ethers-buliding-blocks

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, COA of Formula: C4H9BrO

A. 2-Ethoxyethoxynitrobenzene 2-Nitrophenol (91.0 g. 0.65 mole), 2-bromoethyl ethyl ether (100.0 g. 0.65 mole), anhydrous potassium carbonate (9.0 g, 0.72 mole) and acetone (1 liter) were refluxed for 65 hours. The reaction mixture was filtered, and the acetone removed by rotary evaporation. The residue was partitioned between 200 ml. of dichloromethane and 100 ml water. The organic phase was further washed with 200 ml. of 10% sodium hydroxide followed by 100 cc of water. The product (58.0 g) was obtained in 42% yield by a vacuum distillation (100-120 C./0.5 mm).

At the same time, in my other blogs, there are other synthetic methods of this type of compound, 1-Bromo-2-ethoxyethane, and friends who are interested can also refer to it.

Reference:
Patent; GAF Corporation; US4178168; (1979); A;,
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Electric Literature of 36942-56-0,Some common heterocyclic compound, 36942-56-0, name is 2-Bromo-4-methoxy-1-methylbenzene, molecular formula is C8H9BrO, 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.

A RBF was charged with (1,5-cyclooctadiene)(methoxy)-iridium(i) dimer (0.049 g, 0.075 mmol), 4,4′-di-tert-butyl-2,2′-dipyridyl (0.040 g, 0.149 mmol), and bis(pinacolato)diboron (1.339 g, 5.27 mmol). The flask was flushed with Ar (g), then hexane (15.30 ml) was added. A reflux condenser was attached to the flask, and the flask was heated to 50 C. for 10 minutes. 2-bromo-4-methoxy-1-methylbenzene (2.0 g, 9.95 mmol) was added and the reaction was stirred overnight at 50 C. The reaction was diluted with ethyl acetate and washed with water. The aqueous layer was extracted with ethyl acetate, and the combined organic layers were dried with sodium sulfate, filtered, and concentrated. The material was purified via column chromatography (RediSep Gold 80 g, gradient elution 0-50% EtOAc:Heptane) to afford 2-(4-bromo-2-methoxy-5-methylphenyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane (0.694 g, 2.122 mmol, 21.33% yield) as an off-white oily solid. m/z (ESI) 329.1 (M+H)+.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 2-Bromo-4-methoxy-1-methylbenzene, its application will become more common.

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;,
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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. 27060-75-9, name is 1-Bromo-4-methoxy-2-methylbenzene, A new synthetic method of this compound is introduced below., HPLC of Formula: C8H9BrO

In a four-necked flask equipped with a thermometer, reflux condenser, stirrer, and nitrogen introduction tube,Add 200g of N-methylpyrrolidone and 15.0g (0.11mol) of acetanilide, stir to dissolve acetanilide in N-methylpyrrolidonein.Add 22g (0.12mol) of 30wt% sodium methoxide and gradually heat to 100 C to distill off methanol to prepare acetanilide sodium salt solution.Add 20.2 g (0.1 mol) 4-bromo-3-methylanisole to the reaction bottle at 20 C for 30 minutes,Control the temperature of the material ? 40 , after the addition is complete, continue to stir the reaction at 40 for 45 minutes.15g of methanol was added, and the temperature was raised to 100 C within 30 minutes, and the low-boiling fraction was distilled off. Then, the reaction was continued at 100 C for 30 minutes.Finally, under vacuum conditions, the temperature is controlled within the range of 110-130 C, and N-methylpyrrolidone is distilled off,A reaction mixture containing the target product 4-methoxy-2-methyldiphenylamine was obtained. Add 200 g of water to the reaction mixture containing 4-methoxy-2-methyldiphenylamine and stir well,Dissolve soluble materials and filter to obtain crude 4-methoxy-2-methyldiphenylamine.The crude 4-methoxy-2-methyldiphenylamine is post-treated by methanol recrystallization, centrifugal separation, drying, etc.Obtained target product 4-methoxy-2-methyldiphenylamine 20.5g, purity 99.3%(Gas chromatography analysis),The reaction yield was 95.3% (based on 4-bromo-3-methylanisole).

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; Shandong Dao Ke Chemical Co., Ltd.; Shandong Morui Technology Co., Ltd.; Li Mingxin; Lu Fengyang; Wang Jiahui; Yang Shuren; Li Mingjing; Yan Xue; (13 pag.)CN104628585; (2016); B;,
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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. 3616-56-6, name is 2,2-Diethoxy-N,N-dimethylethanamine, A new synthetic method of this compound is introduced below., Quality Control of 2,2-Diethoxy-N,N-dimethylethanamine

Example 2 (E)-4-Dimethylamino-But-2-Enoic acid-[4-(3-Chloro-4-Fluoro-Phenylamino)-7-((S)-Tetrahydrofuran-3-Yloxy)-Quinazolin-6yl]-Amide 5.6 litres of 30percent hydrochloric acid (53.17 mol) are added to 4.4 litres of water. Then 4.28 kg of 95percent (dimethylamino)-acetaldehyde-diethylacetal (26.59 mol) are added dropwise within 20 minutes at 30° C. The reaction solution is stirred for 8 hours at 35° C. stirred, cooled to 5° C. and stored under argon. This solution is referred to as solution B. 4.55 kg (68.06 mol) of potassium hydroxide are dissolved in 23.5 litres of water and cooled to -5° C. This solution is referred to as solution C. 5.88 kg (10.63 mol) of diethyl ((4-(3-chloro-4-fluoro-phenylamino)-7-(tetrahydrofuran-3-yloxy)-quinazoline-6-ylcarbamoyl)-methyl)-phosphonate and 0.45 kg of lithium chloride (10.63 mol) are placed in 23.5 litres of tetrahydrofuran and cooled to -7° C. The cold solution C is added within 10 minutes. Then solution B is added at -7° C. within 1 hour. After stirring for a further hour at -5° C. the reaction mixture is heated to 30° C. and combined with 15 litres of water. After cooling to 3° C. the suspension is suction filtered, the precipitate is washed with water and dried. Yield: 5.21 kg of crude product, 100percent, water content: 6.7percent The crystallisation of the crude product is carried out with butyl acetate/methylcyclohexane Yield: 78percent purity HPLC 99.4Fl percent, water content 5.4percent

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; Boehringer Ingelheim International GmbH; US2005/85495; (2005); A1;,
Ether – Wikipedia,
Ether | (C2H5)2O – PubChem

Synthetic Route of 349-55-3, 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. 349-55-3, name is 3-Methoxy-5-(trifluoromethyl)aniline belongs to ethers-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below.

1 3-(3-Methoxy-5-trifluoromethyl-phenylamino)-2-methylsulfonyl-3-methylsulfanyl-propenenitrile To a solution of 3-methoxy-5-trifluoromethyl-anilin(1.50 g, 7.8 mmol) in dry ethyl acetate (10 ml) thiophosgene (0.20 ml, 2.6 mmol) was added dropwise. After stirring for 1.5 h at 75 C. the reaction mixture was cooled on an ice bath and then filtered. The filtrate was concentrated. The residue was dissolved in dry acetone (5 ml) and added to a suspension of methanesulfonylacetonitrile (0.34 g, 2.6 mmol) and dry potassium carbonate (0.72 g, 5.2 mmol) in dry acetone (5 ml). The resulting mixture was stirred at room temperature under nitrogen for 19 h, and then filtered. To the filtrate methyl iodide (0.49 ml, 7.8 mmol) was added. The mixture was stirred at room temperature for 1.5 h. The reaction mixture was concentrated and the residue was taken up into dichloromethane and water. The organic layer was washed with water (2X), dried (sodium sulfate) and concentrated. The residue was recrystallized from ethyl acetate to give 0.70 g (73%) of the title compound. 1H NMR (200 MHz, CDCl3): delta=2.28 (s, 3H), 3.22 (s, 3H), 3,87 (s, 3H), 7.0 (t, 1H), 7.05 (br s, 1H), 7.14 (br s, 1H), 9.8 (br s, 1H); El SP/MS: 366 (M-2).

The synthetic route of 3-Methoxy-5-(trifluoromethyl)aniline has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Hansen, John Bondo; Tagmose, Tina Moller; Mogensen, John Patrick; Dorwald, Florencio Zaragoza; Jorgensen, Anker Steen; US2001/25111; (2001); A1;,
Ether – Wikipedia,
Ether | (C2H5)2O – PubChem

Reference of 1836-62-0, 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. 1836-62-0, name is 2-(2-Methoxyphenoxy)ethylamine belongs to ethers-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below.

General procedure: Corresponding 2-(aryloxymethyl)oxiranes (5 mmol, 1 equiv) and amines (7.5 mmol, 1.5 equiv) were dissolved in 30 mL i-PrOH. The reaction was purged with argon 3 times and stirred at reflux for 5 h, andthen the mixture was cooled to room temperature and added AcOEt.After washing with brine 3 times, the organic layer was dried overanhydrous Na2SO4, filtered, and evaporated in vacuo. Purification ofthe crude residue by column chromatography on silica gel yielded target compounds.

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

Reference:
Article; Chang, Qi; Chen, Zhuo; Hu, Gaoyun; Hu, Liqing; Li, Qianbin; Long, Jing; Bioorganic and medicinal chemistry; vol. 28; 9; (2020);,
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Application of 366-99-4, 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 366-99-4 as follows.

2-pentanone (17.2 g, 200 mmol), Acetic acid (1.8 g, 30 mmol), and Sodium triacetoxyborohydnde (6.36 g, 30 mmol) were added to a solution of 3-Fluoro-4-methoxyaniline (2.82 g, 20 mmol) in DCM (120 mL) and the mixture was stined at RT for 12 hr. Water was added to quench the reaction and the mixture was extracted with DCM. The solvent was removed under and the residue was purified by silica gel chromatography to afford 3-Fluoro-4-methoxy-N-(pentan-2-yl)aniline(2.1 g, 50percent yield). MS m/z=212 [M+H].

According to the analysis of related databases, 366-99-4, the application of this compound in the production field has become more and more popular.

Reference:
Patent; JIANGSU ASCENTAGE BIOMED DEVELOPMENT INC.; CHEN, Jianyong; ZHOU, Yunlong; WANG, Shaomeng; GUO, Ming; YANG, Dajun; JIAO, Lingling; JING, Yu; QIAN, Xu; LIU, Liu; BAI, Longchuan; YANG, Chao-Yie; MCEACHERN, Donna; WO2015/127629; (2015); A1;,
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910251-11-5, name is Potassium trifluoro(methoxymethyl)borate, belongs to ethers-buliding-blocks compound, is considered to be a conventional heterocyclic compound, which is widely used in drug synthesis. The chemical synthesis route is as follows. COA of Formula: C2H5BF3KO

Under an argon atmosphere a mixture of 70 mg of tert-butyl 10-bromo-8-cyclopropyl-3,4,7,8-tetrahydro-1H-[1,4]diazepino[6,7,1-ij]quinoline-2(6H)-carboxylate (0.172 mmol, 1.00 eq) from step 8.2, 52.2 mg of potassium trifluoro (2-methoxymethyl)borate (0.344 mmol, 2.00 eq), 168 mg of cesium carbonate (0.516 mmol, 3.00 eq), 1.43 mg of Pd(OAc)2 (0.006 mmol, 0.04 eq) and 5.73 mg of X-Phos (0.012 mmol, 0.07 eq) in degassed dioxane (4 mL) and water (0.5 mL) was heated in a microwave at 130 C. for 40 h. Then the mixture was extracted with DCM and the organic phase was washed with water and dried over MgSO4, filtrated and solvent was evaporated to yield the title compound. ESI-MS: m/z (%): 373.30 (100, [M+H]+).

The synthetic route of 910251-11-5 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; AbbVie Deutschland GmbH & Co. KG; BACKFISCH, Gisela; BAKKER, Margaretha Henrica Maria; BLAICH, Guenter; BRAJE, Wilfried; DRESCHER, Karla; ERHARD, Thomas; HAUPT, Andreas; KOOLMAN, Hannes; LAKICS, Viktor; LINSENMEIER, Anna; MACK, Helmut; PETER, Raimund; RELO, Ana Lucia; US2015/259343; (2015); A1;,
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Ether | (C2H5)2O – PubChem

Electric Literature of 7664-66-6, 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. 7664-66-6 name is 4-Isopropoxyaniline, 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.

The compound obtained in Step 5 (19 mg) was dissolved in dioxane (1 mL), 4 isopropoxyphenylaniline (12mg) and 4N hydrochloric acid dioxane (64muL), and the mixture was stirred for 20 minutes in a microwave irradiation under 180 . The reaction solution was extracted three times with chloroform after adding a saturated aqueous sodium hydrogen carbonate solution, and the organic layer was concentrated after dried over sodium sulfate. The resulting residue to give the title compound purified by silica gel column chromatography (13mg, 57%).

At the same time, in my other blogs, there are other synthetic methods of this type of compound, 4-Isopropoxyaniline, and friends who are interested can also refer to it.

Reference:
Patent; TAIHO PHARMACEUTICAL COMPANY LIMITED; MINAMIGUCHI, KAZUHISA; OKAJIMA, SHIGEO; AOKI, SHINICHI; ASAI, MASANORI; ASAI, TAKAHIRO; YAMANAKA, HIROYOSHI; DOHI, SUGURU; (149 pag.)JP5851663; (2016); B1;,
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Adding a certain compound to certain chemical reactions, such as: 261762-35-0, name is 5-Bromo-1,2-difluoro-3-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 261762-35-0, Computed Properties of C7H5BrF2O

To a mixture of 6-methoxy-1,2,3,4-tetrahydro-2,7-naphthyridine (500 mg, 3.04 mmol) and 5-bromo-2,3-difluoroanisole (883 mg, 3.96 mmol) in dioxane (8 mL) was added t-BuONa (438 mg, 4.56 mmol), Pd2(dba)3 (40 mg, 0.04 mmol) and Ruphos (30 mg, 0.06 mmol) under N2. After being heated with stirring at 100 C for 12 hrs, the resulting reaction mixture was filtered. Thefiltrate was concentrated in vacuo, diluted with DCM (100 mL), washed with water (30 mL) and brine (30 mL), dried over anhydrous Na2SO4 and concentrated in vacuo. The residue was purified by flash column to give 2- (3 ,4-difluoro-5-methoxy-phenyl)-6-methoxy-3 ,4-dihydro- 1H- 2,7-naphthyridine (560 mg) as a gray 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; F. HOFFMANN-LA ROCHE AG; HOFFMANN-LA ROCHE INC.; CHENG, Zhanling; WANG, Min; YANG, Song; (208 pag.)WO2016/107832; (2016); A1;,
Ether – Wikipedia,
Ether | (C2H5)2O – PubChem