Tag: M.W=200-300

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. 5111-65-9, name is 2-Bromo-6-methoxynaphthalene, This compound has unique chemical properties. The synthetic route is as follows., name: 2-Bromo-6-methoxynaphthalene

Step 21.2: 6-methoxy-naphthalen-2-ylamine A solution of 2-bromo-6-methoxy-naphthalene (237 mg, 1 mmol), Pd (dba)2 mg, 0.05 mmol), tri-t-buthylphosphonium tetrafluoroborate (14 mg, 0.05 mmol), and lithium bis (trimethylsilyl)amide (1 M in hexane, 1.1 mL, 1.1 mmol) is stirred in toluene (2.5 mL) under argon for 6 h. The reaction mixture is taken in diethyl ether (20 mL), and quenched with 1 M HCI. The organic phase is extracted with water, the combined aqueous phases are treated with 1 M sodium hydroxide and extracted with DCM. The combined organic phases are dried over magnesium sulfate, the solvent is evaporated in vacuo and the residue is purified by column flash chromatography on silica gel (ethyl acetate) to afford 6-methoxy- naphthalen-2-ylamine (110 mg, 64 %), HPLC tR : 3.07, (M+H) + = 173.9.

Chemical properties determine the actual use. Each compound has specific chemical properties and uses. We look forward to more synthetic routes in the future to expand reaction routes of 5111-65-9.

Reference:
Patent; NOVARTIS AG; NOVARTIS PHARMA GMBH; WO2005/97135; (2005); A2;,
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These common heterocyclic compound, 75148-49-1, name is 3-Bromobenzaldehyde Diethyl Acetal, 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: C11H15BrO2

Step 1: Preparation of 3-(3-aminooxetan-3-yl)benzaldehyde Hydrochloride 3-Bromobenzaldehyde diethyl acetal (11.65 g, 45 mmol) in dry THF (100 mL) at -78 C. was added n-butyl lithium (2.5 M in hexanes, 19 mL, 47 mmol) dropwise. The sample was stirred at -78 C. for ten minutes then added 2-methyl-N-(oxetan-3-ylidene)propane-2-sulfonamide (7.5 g, 43 mmol) dropwise. The sample was stirred at -78 C. for one hour. The mixture was diluted with 200 mL saturated ammonium chloride solution and 200 mL ethyl acetate. The layers were shaken and separated and the organic phase was dried over magnesium sulfate and concentrated under reduced pressure. The crude mixture was dissolved in ethyl acetate (250 mL). The reaction mixture was cooled to 0 C. was added 1M hydrochloric acid in ethyl acetate dropwise (24 mL, 24 mmol). The reaction mixture was stirred at 0 C. for one hour then vacuum filtered to give the desired product as a slightly off white solid (1.97 g, 9.2 mmol). 1H NMR (400 MHz, DMSO-d6) delta 10.08 (s, 1H), 9.18 (s, 3H), 8.09 (s, 1H), 8.01 (d, J=7.9 Hz, 1H), 7.91 (d, J=7.9 Hz, 1H), 7.79-7.73 (m, 1H), 5.03-4.91 (m, 4H).

The synthetic route of 3-Bromobenzaldehyde Diethyl Acetal has been constantly updated, and we look forward to future research findings.

Reference:
Patent; AMGEN INC.; CYTOKINETICS, INC.; Ashcraft, Luke; Boezio, Alessandro; Butler, John; Chandra, Aroop; Chuang, Chihyuan; Collibee, Scott E.; Debenedetto, Mikkel; DiMassa, Vincent; Graceffa, Russell; Malinowski, Justin; Moebius, David; Morgan, Bradley P.; Payette, Joshua; Romero, Antonio; St. Jean, JR., David; Vargas, Richard; Yeoman, John; Zhang, Hanmo; (146 pag.)US2019/77793; (2019); A1;,
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These common heterocyclic compound, 18800-30-1, name is 1-Bromo-4-(2-bromoethoxy)benzene, 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. HPLC of Formula: C8H8Br2O

A mixture of B32.1 (4.3 g, 25mmol), CH3SNa (6.12 g, 4Smmol) in DMF (50 mL) was heated at 90 C for 18 h. DCM (50 mL) and water (100 mL) was added. The organic phase was separated andconcentrated to give the title compound (2.9 g, 80%). The crude product was used in the next step without further purification.

The synthetic route of 1-Bromo-4-(2-bromoethoxy)benzene has been constantly updated, and we look forward to future research findings.

Reference:
Patent; NOVARTIS AG; CHAN, Ho Man; FU, Xingnian; GU, Xiang-Ju Justin; HUANG, Ying; LI, Ling; MI, Yuan; QI, Wei; SENDZIK, Martin; SUN, Yongfeng; WANG, Long; YU, Zhengtian; ZHANG, Hailong; ZHANG, Ji Yue (Jeff); ZHANG, Man; ZHANG, Qiong; ZHAO, Kehao; (148 pag.)WO2017/221100; (2017); A1;,
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Electric Literature of 13940-96-0, These common heterocyclic compound, 13940-96-0, name is 4-Phenoxybenzene-1,2-diamine, 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.

For preparing the 3,4-diamino-diphenyl ether used as starting material, 172.5 g of 5-chloro-2-nitro-aniline were heated for 4 hours under reflux in 500 ml of dimethylformamide with 94 g of phenol in the presence of 150 g of anhydrous potassium carbonate. After cooling, the reaction mixture was diluted with 1000 ml of water, the 3-amino-4-nitro-diphenyl ether that had precipitated was filtered off with suction and purified by recrystallization from isopropanol. Yield: 110 g; melting point: 142C. 103 g Of the 3-amino-4-nitro-diphenyl ether so obtained were hydrogenated in 800 ml of dimethylformamide with Raney nickel under a pressure of 100 atmospheres gauge at room temperature, the catalyst was then removed by filtration and the solution was evaporated under reduced pressure. The 3,4-diamino-diphenyl ether that had formed was obtained in the form of a sirupy mass which was dissolved in ethanol and used in the reaction as described above.

The synthetic route of 13940-96-0 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Hoechst Aktiengesellschaft; US3954791; (1976); A;,
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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. 1462-37-9, name is ((2-Bromoethoxy)methyl)benzene belongs to ethers-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below. Safety of ((2-Bromoethoxy)methyl)benzene

0.24 g (10 mmo 1) sodium hydride and 15 ml of N, N-dimethylformamide were added to a 50 ml round bottom flask,Stirred at room temperature for 10 minutes,Followed by the addition of 2.5 g (lOmmol) of compound 2 and 1 O of 2-octyloxyethyl bromide,And the reaction was carried out by thin layer chromatography to the end of the reaction. The reaction solution was then poured into 500 ml of ice water and extracted three times with 100 ml of ethyl acetate. The organic phase was combined and the solvent was evaporated. The residue was purified by WATFif = 100: 1 ) To give Compound 3 (2.7 g, 71% yield)

The synthetic route of 1462-37-9 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Guangxi Normal University; Chen Zhenfeng; Liang Hong; Liu Yancheng; Li Liangping; Lu Xing; (13 pag.)CN106478675; (2017); A;,
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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 954235-83-7 as follows. HPLC of Formula: C7H4BrF3O

A mixture of l-bromo-2-(difluoromethoxy)-4-fluorobenzene (intermediate 176a, 150 mg), (4-(2- (4-(ethylsulfonyI)phenyl)acetamido)-2,6-difluorophenyl)boronic acid (intermediate 122a, 404 mg), tri-ierf-butylphosphine, tetrafluoroboric acid salt (217 mg), Pd2(dba)j (171 mg) and sodium carbonate solution (2 M, 1.245 mL) in 1,4-dioxane (4.5 mL) was sealed in a vessel and heated in the microwave at 100C for 45 mins. The reaction mixture was filtered through celite and silica gel. The filtrate was concentrated under reduced pressure and the residue was purified by MDAP to afford N-(2′- (difluoromethoxy) -2,4′,6-trifiuoro-[ 1 , 1 ‘-biphenyl] -4-yl) -2-(4-(ethylsulfonyl)phenyl) acetamide ( 133 mg) as a yellow solid. ?-NMR (400 MHz, DMSO-Patent; GLAXO GROUP LIMITED; WANG, Yonghui; CAI, Wei; LIU, Qian; MENG, Qinghua; CHENG, Yaobang; YANG, Ting; ZHANG, Guifeng; XIANG, Jianing; WU, Chengde; WO2013/29338; (2013); 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. 92248-06-1, name is Bis(3-methoxyphenyl)amine, A new synthetic method of this compound is introduced below., category: ethers-buliding-blocks

(3) The third step: under argon protection, add to the double-mouth bottle4,4 ‘, 4 “, 4” -tetrabromostatrene,3,3’-dimethoxydianiline, palladium acetate, sodium tert-butoxide and tri-tert-butylphosphine, adding 5 mL of toluene, stirring and placing at 130 C., reacting for 12 hours, stopping the reaction, adding saturated chlorinated The ammonium solution was extracted three times with dichloromethane and the organic layer was dried over anhydrous MgSO4. The crude product was subjected to silica gel column chromatography (petroleum ether: dichloromethane = 2: 3, v / v)A yellow solid was obtained,Recrystallization from tetrahydrofuran / petroleum ether. The product TPE-OMe-mm, the product of the formula as shown in formula (VI):

The synthetic route of 92248-06-1 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Sun Yat-sen University; Shao Guang; Kuang Daibin; He Yanjian; Chen Jian; (17 pag.)CN105037179; (2017); B;,
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Electric Literature of 5414-19-7, 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.

The product of Part F (5.0 g, 10.6 mmol), 18-crown-6 (Aldrich, 0.5 g, catalytic amount), potassium carbonate (Aldrich, 4.4 g, 31.8 mmol), and bis(bromoethyl)ether (Aldrich, 4.9 g, 21.2 mmol) were slurried in N,N-dimethylformamide (20 ml) and stirred at 65 C. for 15 hr. Afterward, the mixture was diluted with water (50 ml) and extracted with ethyl acetate (3?100 ml). The organics were combined and washed with water (twice), washed with brine (twice), dried over Na2SO4, and concentrated for a tan oil. The oil was washed with hexanes, and then dried to afford a tan oil. The tan oil was recrystallized from methanol to afford the desired intermediate in the form of a white solid (2.5 g, 44% yield). 1H NMR and LCMS showed desired intermediate.

The chemical industry reduces the impact on the environment during synthesis 1-Bromo-2-(2-bromoethoxy)ethane. I believe this compound will play a more active role in future production and life.

Reference:
Patent; Barta, Thomas E.; Becker, Daniel P.; Bedell, Louis J.; Boehm, Terri L.; Brown, David L.; Carroll, Jeffery N.; Chen, Yiyuan; Fobian, Yvette M.; Freskos, John N.; Gasiecki, Alan F.; Grapperhaus, Margaret L.; Heintz, Robert M.; Hockerman, Susan L.; Kassab, Darren J.; Khanna, Ish K.; Kolodziej, Stephen A.; Massa, Mark A.; McDonald, Joseph J.; Mischke, Brent V.; Mischke, Deborah A.; Mullins, Patrick B.; Nagy, Mark A.; Norton, Monica B.; Rico, Joseph G.; Schmidt, Michelle A.; Stehle, Nathan W.; Talley, John J.; Vernier, William F.; Villamil, Clara I.; Wang, Lijuan J.; Wynn, Thomas A.; US2005/9838; (2005); A1;,
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Synthetic Route of 1663-61-2,Some common heterocyclic compound, 1663-61-2, name is (Triethoxymethyl)benzene, molecular formula is C13H20O3, 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: The orthoester (1.5 equiv) was added to a mixture of the 2-aminobenzamide (1.0 equiv) in absoluteethanol (3 mL). Glacial acetic acid (2 equiv) was added and the reaction was heated at reflux for 12?24 h.The reaction mixture was cooled and concentrated under vacuum. If the crude product was pure by1H-NMR, it was triturated with 5percent ether in pentane. If it was not pure, it was recrystallized fromethanol. In some cases, it was necessary to remove excess orthoester under high vacuum at 50 ¡ãC prior to purification. The following compounds were prepared:

The synthetic route of 1663-61-2 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Gavin, Joshua T.; Annor-Gyamfi, Joel K.; Bunce, Richard A.; Molecules; vol. 23; 11; (2018);,
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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. 20469-65-2, name is 1-Bromo-3,5-dimethoxybenzene, This compound has unique chemical properties. The synthetic route is as follows., Quality Control of 1-Bromo-3,5-dimethoxybenzene

Condensation reaction: in with a thermometer, condenser 250 ml bottle to join four 21.9g 5 – bromo – m dimethyl ether {melting point 62 – 66 C; appearance: white solid; nuclear magnetic:1H NMR (CDCl3, 400MHz) delta (ppm) data are as follows: 3.82 (s, 6H, CH3), 6.37 (t, 1H, Ar – H), 6.81 (d, 2H, Ar – H)}, 12.8g bromopropylene, 20.4g triethylamine, 2.2g dppp nickel chloride, 130 ml methyl tert-butyl ether, magnetic stirring, oil bath heating, when the temperature rises to 50 C and maintaining at 4 hours, after the reaction is cooled to ambient temperature, for 60 ml 10% hydrochloric acid aqueous solution washing the reaction liquid, water washed to neutral, the organic layer is distilled under reduced pressure to obtain 17.4g 5 – propenyl – m dimethyl ether {melting point 97 – 100 C; appearance: white solid; nuclear magnetic resonance:1

According to the analysis of related databases, 20469-65-2, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Weifang Xian Da Chemical Co., Ltd.; Li Kai; Wang Guangyue; Yang Qiwei; Zou Yabo; (7 pag.)CN106748673; (2017); A;,
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