Author: Jessica.F

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 10103-06-7 as follows. Application In Synthesis of 2,3-Dimethoxynaphthalene

EXAMPLE 9 2-(4-Chlorobutyl)-6,7-dimethoxynaphthalene Aluminum chloride (25.5 g, 0.19 mole) was added to a solution of 21.5 mL (0.19 mole) of 4-chlorobutyryl chloride in 225 mL of methylene chloride. To the resulting solution, cooled in an ice bath, was added dropwise a solution of 30.0 g (0.16 mole) of 2,3-dimethoxynaphthalene in 150 mL of methylene chloride over 30 minutes. The reaction mixture was stirred at 3 C. for 30 minutes and at 24 C. for 17 hours. The reaction mixture was worked up as Example 5 and the crude product was recrystallized from acetone-hexane, to give 31.5 g (68% yield), mp 98-99, of 4-chloro-1-(6,7-dimethoxy-2-naphthalenyl)-1-butanone. Anal Calcd. for C16 H17 ClO3: C, 65.64; H, 5.85; Cl, 12.11. Found: C, 65.33; H, 5.77; Cl, 12.16.

According to the analysis of related databases, 10103-06-7, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Hoffmann-La Roche Inc.; US4937371; (1990); A;,
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Related Products of 876-32-4,Some common heterocyclic compound, 876-32-4, name is 4-Methoxy-N-methylbenzylamine hydrochloride, molecular formula is C9H14ClNO, 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.

In a sealed tube, mixture of benzamide 24b (38 mg, 0.11 mmol), formaldehyde (37% in water, 0.043 mL, 0.55 mmol), 1-(4-methoxyphenyl)-N-methylmethanamine hydrochloride (102 mg, 0.55 mmol), and 1N NaOH (0.5 mL) in H2O:THF (1 mL:0.5 mL) was heated at 65 C for 2 hours. After cooling to room temperature, the reaction mixture was diluted with ethyl acetate, washed with brine, dried over Na2SO4, and concentrated, then purified by column chromatography to afford the pure product (28 mg, 57% yield) as off white solid. 1H NMR (CDCl3, 300 MHz) delta: 7.73 (d, J= 1.8 Hz, 1H), 7.49 (d, J= 8.7 Hz, 1H), 7.36 (dd, J= 1.8, 8.7 Hz, 1H), 7.23 (d, J= 8.7 Hz, 2H), 7.20- 7.13 (m, 1H), 6.91-6.84 (m, 1H), 6.85 (d, J= 8.7 Hz, 2H), 6.17 (bs, 1H), 5.35 (s, 2H), 4.38 (d, J= 6.3 Hz, 2H), 3.79 (s, 3H), 3.59 (s, 2H), 2.32 (s, 3H).

The synthetic route of 876-32-4 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; RUTGERS, THE STATE UNIVERSITY OF NEW JERSEY; UNIVERSITY OF MEDICINE AND DENTISTRY OF NEW JERSEY; LAVOIE, Edmond J.; PARHI, Ajit; ZHANG, Yongzheng; PILCH, Daniel S.; KAUL, Malvika; WO2013/142712; (2013); A1;,
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These common heterocyclic compound, 64465-53-8, name is 4-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. name: 4-Fluoro-3-methoxyaniline

INTERMEDIATE PREPARATION 145-a nolTo a solution of 4-fluoro-3-(methyloxy)aniline (3.8 g, 26.92 mmol) in methylene chloride (50 mL) at 0C was added boron tribromide (20.2 g, 80.77 mmol). The mixture was quenched with methanol and concentrated in vacuo. The residue was dissolved in methanol and reconcentrated two times. The residue was dissolved in water and NaHC03 was added. The resulting solution was extracted with ethyl acetate, washed with brine, dried over MgS04, filtered and concentrated to afford 5-amino-2-fluorophenol (3.0 g).

The synthetic route of 4-Fluoro-3-methoxyaniline has been constantly updated, and we look forward to future research findings.

Reference:
Patent; GLAXOSMITHKLINE LLC; BROOKS, Carl, A.; CHEUNG, Mui; EIDAM, Hilary, S.; FOX, Ryan, M; HILFKER, Mark, A.; MANAS, Eric, S.; YE, Guosen; WO2011/119704; (2011); A1;,
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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. 103-50-4, name is Benzyl ether belongs to ethers-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below. Formula: C14H14O

General procedure: In the mixture of cyclic/acyclic ether (11 mmol) and acid chloride (10 mmol), nano-ZnO (5 mol%) was added at 0-5 C and stirred at room temperature for an appropriate time. After the TLC monitoring reaction, the ZnO was removed by filtration and washed repeatedly with dichloromethane and water. It was then dried at 60 C for 3 h and used for the next catalytic cycle. The solution was extracted three times with dichloromethane and water, and dried on anhydrous Na2SO4. The product was purified on a silica gel column chromatography using a mixture of petroleum ether/ethyl acetate (150:1, v/v). The product is obtained by vacuum distillation to remove the solvent. The compounds were characterized by 1H NMR and 13C NMR.

The synthetic route of 103-50-4 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Chen, Junqing; Feng, Chengliang; Ji, Min; Tang, Yuqi; Wang, Wei; Yang, Wanfeng; Chemical Papers; (2020);,
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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. 5414-19-7, name is 1-Bromo-2-(2-bromoethoxy)ethane, This compound has unique chemical properties. The synthetic route is as follows., Recommanded Product: 1-Bromo-2-(2-bromoethoxy)ethane

To a stirred solution of 3-amino-1-bromoisoquinoline (444 mg, 2.00 mmol) in anhydrous dimethylformamide (10 mL) was added sodium hydride (60%, unwashed, 96 mg, 2.4 mmol) in one portion. The mixture was stirred at 25 C. for 5 min before 2-bromoethyl ether (90%, 250 muL, 2.00 mmol) was added. The mixture was stirred further at 25 C. for 5 h and at 75 C. for 72 h before it was cooled to 25 C., quenched with saturated ammonium chloride solution and diluted with ethyl acetate. The organic layer was separated, washed with water and brine, dried over Na2SO4, filtered and concentrated. Purification of the residue on silica gel eluting with 0% to 70% ethyl acetate/hexanes afforded Cap-143, step a as a yellow solid (180 mg, 31%). Rt=1.75 min (Cond.-MS-WI); 90% homogenity index; LCMS: Anal. Calc. for [M+H]+ C13H4BrN2O: 293.03; found: 293.04.

According to the analysis of related databases, 5414-19-7, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Bristol-Myers Squibb Company; US2009/233925; (2009); A1;,
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Reference of 101-55-3, A common heterocyclic compound, 101-55-3, name is 1-Bromo-4-phenoxybenzene, molecular formula is C12H9BrO, 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.

General procedure: Suzuki-coupling reaction was carried out in a 25mL round bottom (RB) flask. Initially, RB was cleaned with water and then rinsed with acetone followed by drying at 60C in an oven for one hour. One mmol of bromobenzene and two mmol of phenylboronic acid were poured into RB. Subsequently, 2mL of toluene was inserted into the RB and closed with a rubber septum. The reaction solution was purged with N2 gas for 30min for the complete removal of air from the mixture. After that, RB was charged with 30mg of Ag/TiO2 photocatalyst, and the vessel was sealed with the rubber septum. The reaction mixture again purged with the N2 gas for the residual air and then irradiated with the 20W white LED (lambda ~ 420nm) for 24h. The sample was analyzed with TLC after every two-hour interval. The conversion and the yield were determined with GC-FID (Thermo equipped with Stabilwax w/Integra- Guard 30-m-long column), and confirmation was obtained by the 1H and 13C NMR of the pure samples.

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; Chen, Yuning; Feng, Li; Journal of Photochemistry and Photobiology B: Biology; vol. 205; (2020);,
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Electric Literature of 38336-04-8,Some common heterocyclic compound, 38336-04-8, name is 2-(Benzyloxy)-1-ethanamine, 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.

To a solution of(2S,3R,4R,5S,6R)-6-(acetoxymethyl)-3-isothiocyanato-tetrahydro-2H-pyran-2,4,5-triyl triacetate (9.8 g, 25 mmol) in dichloromethane (100 mL) was added 128 (4 g, 26 mmol) at 0 C. After stirred for 2 hours, trifluoro acetic acid (15.4 g, 159 mmol) was added. The resulting solution was stirred for 12 hours at room temperature, then quenched with ice- water (200 mL) and neutralized by the addition ofNaHCC”3 (26 g, 318 mmol). The organic layer was separated and the aqueous layer was extracted with dichloromethane (3×100 mL). The combined organic layer was washed with brine (2×100 mL), dried over anhydrous sodium sulfate, and concentrated under vacuum to give a residue, which was purified by silica gel column, eluted with 10 % – 50 % ethyl acetate in petroleum ether to afford 129 as a white syrup (9.8 g, 77 %). (ES, m/z) [M+H]+ 481.0; 1H NMR (300 MHz, CDC13) delta 7.31 – 7.38 (m, 5H), 6.24 (d, / = 6.3 Hz, 1H), 5.41 – 5.43 (m, 1H), 4.94 – 4.98 (m, 1H), 4.55 (s, 2H), 4.34 – 4.37 (m, 1H), 4.14 – 4.16 (m, 3H), 3.83 – 3.87 (m, 1H), 3.64 (t, / = 5.4 Hz, 2H), 3.53 (t, / = 5.1 Hz, 2H), 2.12 (s, 3H), 2.10 (s, 3H), 2.09 (s, 3H).

The synthetic route of 38336-04-8 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; ALECTOS THERAPEUTICS INC.; MERCK SHARP & DOHME CORP.; CHANG, Jiang; LIU, Kun; MCEACHERN, Ernest J.; MU, Changwei; SELNICK, Harold G.; SHI, Feng; VOCADLO, David J.; WANG, Yaode; WEI, Zhongyong; ZHOU, Yuanxi; ZHU, Yongbao; WO2012/62157; (2012); A1;,
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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. 767-91-9, name is 2′-Methoxyphenyl acetylene, A new synthetic method of this compound is introduced below., category: ethers-buliding-blocks

General procedure: To a mixture of alpha-azidoamide 16aa (34 mg, 0.20 mmol) and phenylacetylene (9a; 24 L,0.20 mmol) in t-BuOH/H2O (2 mL, 1:1) were added 0.5 M CuSO4 (0.020 mL, 0.010 mmol) and 1.0 M sodium ascorbate (0.020 mL, 0.020 mmol). The reaction mixture was stirred at room temperature for 1 day, and then the resulting reaction mixture was filtered. The separated solid was washed with H2O and hexanes, and triturated with hexane/EtOAc (10:1) to give the 1-morpholino-2-(4-phenyl-1H-1,2,3-triazol-1-yl)ethanone (2aaa; 52 mg, 96%) as a white solid

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; Lee, Doohyun; Kim, Daehun; Lee, Seungyeon; Kim, Taegeum; Kim, Joobin; Kim, Sohee; Liu, Kwang-Hyeon; Lee, Sangkyu; Bae, Jong-Sup; Song, Kyung-Sik; Cho, Chang-Woo; Son, Youn Kyung; Baek, Dong Jae; Lee, Taeho; Molecules; vol. 20; 11; (2015); p. 19984 – 20013;,
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Reference of 7025-06-1, A common heterocyclic compound, 7025-06-1, name is 1-Bromo-2-phenoxybenzene, molecular formula is C12H9BrO, 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.

Preparation of intermediate C01-A: 1-bromodiphenyl ether (2.49 g, 0.01 mol) was dissolved in 100 mL of dry tetrahydrofuran under nitrogen atmosphere, when the internal temperature of the system was lowered to -75 C,Slowly add 4.8 mL of n-hexane solution of n-butyllithium (2.5 mol/L).After the completion of the dropwise addition, the reaction was kept at -75 C for 2 h, and the temperature was maintained.Add 9,9-dimethyl-5H,9H-quinoline[3,2,1-de]acridone solid(2.80g, 0.009 mol), add the insulation reaction for 2h, keep warm,The reaction was continued at room temperature for 2 h, after which 70 g of a 10% by mass dilute hydrochloric acid was added dropwise.Stir for 1 h, separate the liquid, collect the organic phase, remove the solvent, and obtain 5 g of oil;Further, 60 g of glacial acetic acid and 1.0 g of concentrated hydrochloric acid having a concentration of 36.5 wt% were added to the obtained oil.The temperature was raised to reflux, the reaction was kept for 5 hours, the temperature was lowered to 25 C, and 50 g of toluene and 100 g of water were added.The liquid phase is separated, the organic phase is desolvated, the crude oil is passed through a silica gel column, and the petroleum ether is rinsed. The column liquid containing a single product component is collected, and 50 g of petroleum ether is beaten after desolvation, and the filter cake is collected by suction filtration.Obtaining intermediate C01-A,White solid powder 2.52g,Yield 60.4%.

The synthetic route of 7025-06-1 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; CECEP Wanrun Co., Ltd.; Gao Shukun; Zhang Jiangfeng; Sheng Lei; Li Peng; Ma Yongjie; Qin Yuhu; (20 pag.)CN109970775; (2019); A;,
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Electric Literature of 39021-83-5,Some common heterocyclic compound, 39021-83-5, name is 1,4-Dimethoxy-2,3-dimethylbenzene, molecular formula is C10H14O2, 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.

Step 1 2,3-Dimethyl-5,6-dinitro-1,4-dimethoxybenzene A solution of 2,3-dimethyl-1,4-dimethoxybenzene (16.6 g; o.1 mol) in acetic acid (100 mL) was cooled in an ice bath, then conc. HNO3 (40 mL) was added dropwise over 15 minutes. After the addition, the reaction mixture was stirred at ambient temperature for 3 hours, then heated at 50 C. for 20 minutes. Solution was concentrated to 75 mL under vacuum, then poured into ice-H2O (350 mL). The yellow precipitate (8.1 g) was collected. Recrystallization from EtOH gave 5.4 g (18.5% yield) of 2,3-dimethyl-5,6-dinitro-1,4-dimethoxybenzene as a yellow solid, m.p. 147-150 C.

The synthetic route of 39021-83-5 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Wyeth; US6444694; (2002); B1;,
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