Ethers-buliding-blocks

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., 3616-56-6

Synthesis example B17: Synthesis of 8-bromo-12H-benzofuranyl[2,3-a]carbazole (compound 17); (1 7); Under nitrogen, compound 16 (4.6 g, 1 eq) is initially charged and dissolved with acetic acid (185 ml) while heating to reflux. Then (dimethylamino)acetaldehyde diethyl acetal (95percent; 25 g, 10 eq.) is added dropwise to the reaction within 1 h and the mixture is stirred at reflux for 7 h. The mixture is cooled to room temperature and diluted with methylene chloride. In a separating funnel, the organic phase is washed with distilled water and then with saturated NaCI solution. The organic phase is dried with sodium sulfate and concentrated. LC (reverse phase, acetonitrile) gives 1 .35 g of product (27.3percent yield).1 H N MR (CD2CI2; 400 MHz): “5 = 8.73 (s, 1 H), 8.17 (s, 1 H), 8.16 (d, 1 H), 8.08 (d, 1 H), 7.78 (d, 1 H), 7.60 (d, 1 H), 7.56 (m, 2H), 7.49 (dd, 1 H), 7.31 (dd, 1 H).

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; BASF SE; BASF (CHINA) COMPANY LIMITED; KONINKLIJKE PHILIPS ELECTRONICS N.V.; OSRAM OPTO SEMICONDUCTORS GMBH; PHILIPS INTELLECTUAL PROPERTY & STANDARDS GMBH; LANGER, Nicolle; SCHILDKNECHT, Christian; WATANABE, Soichi; FUCHS, Evelyn; WAGENBLAST, Gerhard; LENNARTZ, Christian; MOLT, Oliver; DORMANN, Korinna; HUNZE, Arvid; KRAUSE, Ralf; SCHMID, Guenter; HEUSER, Karsten; VAN ELSBERGEN, Volker; BOERNER, Herbert Friedrich; WO2011/125020; (2011); A1;,
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Some common heterocyclic compound, 929-75-9, name is 1,11-Diamino-3,6,9-trioxaundecane, molecular formula is C8H20N2O3, 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. 929-75-9

General procedure: A mixture of cinnamic acid (6.30 mmol), EDCI (7.50 mmol), DMAP (0.60 mmol), and anhydrous dichloromethane (20 mL) was stirred to dissolve, then diamino-ether (3 mmol) was added and stirred at room temperature for 12 h. Then, the solid was filtered off, the filtrate was added with H2O (50 mL) and extracted by dichloromethane three times. The combined organic layers were washed with H2O and brine, dried with anhydrous sodium sulfate for 8 h, filtered, and evaporated. The resulting residue was purified by preparative TLC with petroleum ether/ethyl acetate = 2:1-1:1 to give pale white solid or light yellow oil.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 929-75-9, its application will become more common.

Reference:
Article; Wang, Jiawen; Hong, Ge; Li, Guoliang; Wang, Wenzhi; Liu, Tianjun; Molecules; vol. 24; 24; (2019);,
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946-80-5, 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. 946-80-5, name is Benzyl Phenyl Ether belongs to ethers-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below.

To 45 mL of the reaction tube were added 0.5 mmol of benzyl phenyl ether, 0.25 mmol of I2, 1.5 mL of acetonitrile solution of nitrosonium tetrafluoroborate (1.5 mL of solution containing 0.1 mmol of nitrosonium tetrafluoroborate), a sealed reaction tube , The temperature was controlled at 30 C, and the reaction was carried out under magnetic stirring for 5 hours, followed by cooling the reaction system to room temperature. The reaction mixture was purified by column chromatography to give 4-benzyloxyiodobenzene with an isolation yield of 60%. The structure of the product was determined using 1H-NMR, 13C-NMR, and GC-MS, see Figures 15-17

The synthetic route of 946-80-5 has been constantly updated, and we look forward to future research findings.

Reference:
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54149-17-6, name is 1-Bromo-2-(2-methoxyethoxy)ethane, 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. 54149-17-6

(2S,6R, I lR)-6,l l -dimethyl-l-oxo- l ,2,3,4,5,6-hexahydro-2,6-methanobenzo[d]azocin-8-y trifluoromethanesulfonate hydrochloride (120 mg, 0.33 mmol), Cs2C03 (214.9 mg, 0.6494 mmol) and mPEG2-Br (78.45 mg, 0.4286 mmol) were dissolved in acetonitrile. The mixture was heated to 75 C for 16 h and cooled to room temperature. The mixture was concentrated under vacuum and purified by flash chromatography to yield (2S,6R,l lR)-8-hydroxy-3-(2- (2-methoxyethoxy) ethyl)-6,l l-dimethyl-3,4,5,6-tetrahydro-2,6-methanobenzo[d]azocin- l(2H)-one (14) (51.5 mg, 47% yield). NMR (500 MHz, CDC13): delta 8.02 (d, 1 H), 6.85 (m, 2H), 4.21-4.23 (m, 2H), 3.89 (t, 2H), 3.57-3.59 (m, 2H), 3.39 (s, 3H), 3.27 (d, 1H), 2.72-2.75 (m, 1 H), 2.55-2.61 (m, 1 H), 2.08-2.13 (m, 1H), 1.87-1.94 (m, 1H), 1.45-1.48 (m, 1H), 1.41 (s, 3H), 0.85 (d, 3H); MS (ESI) for C19H27N04: 334.1965 (MH+). The free base was dissolved in 4M hydrochloride in 2-propanol. The mixture was concentrated to afford product as hydrochloride salt.

Statistics shows that 54149-17-6 is playing an increasingly important role. we look forward to future research findings about 1-Bromo-2-(2-methoxyethoxy)ethane.

Reference:
Patent; NEKTAR THERAPEUTICS (INDIA) PVT.LTD.; NEKTAR THERAPEUTICS (Incorporated under the Laws of Delaware and domiclled in the State of California); DUARTE, FRANCO; ANAND, NEEL; SHARMA, PANKAJ; SINGH, DEVENDRAPRATAP U.; WO2015/79459; (2015); A1;,
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75148-49-1, 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.

To a mixture of 3-bromobenzaldehyde diethylacetal (1.495 g, 5.77 mmol) and bis(triphenylphoshine)palladium(II) dichloride (206 mg, 0.29 mmol) in dimethoxyethane (30 mL) at room temperature under nitrogen, 2-thiopheneboronic acid (1.189 g, 9.29 mmol) and aquesou sodium bicarbonate (1M, 29 mL) were added. The mixture was heated to reflux overnight, cooled to room temperature, and diluted with ethyl acetate. The organic layer was washed with water and brine, dried over magnesium sulfate, filtered, and concentrated. The residue was purified by silica gel chromatography to give a mixture of 2-(3-(diethoxymethyl)phenyl)thiophene and 14-1. This material was taken up in 1:1 methanol:water (30 mL) and concentrated sulfuric acid (1 mL) was added. The mixture was heated to reflux for 2 hours, cooled to room temperature and concentrated. The residue was taken up in ethyl acetate, washed with saturated aqueous sodium bicarbonate, water and brine, dried over magnesium sulfate, filtered and concentrated.

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 75148-49-1.

Reference:
Patent; Aviara Pharmaceuticals, Inc.; Biediger, Ronald J.; Benish, Michele A.; Hardy, Lindsay Bonner; Boyd, Vincent A.; Market, Robert V.; Thrash, Thomas P.; Young, Brandon M.; (83 pag.)US2018/312523; (2018); A1;,
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1535-73-5, 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 1535-73-5 as follows.

General procedure: Two mmol 5b1?5b20 was added to a dichloromethane solution containing 0.3 mL triethylamine at 0 ¡ãC. Then 1.2 equiv. 3-chloropropionyl chloride was dissolved in dry dichloromethane, and the obtained mixture was slowly added to the aniline solution at 0 ¡ãC. The reaction mixture was allowed to slowly warm up to room temperature, extracted with dichloromethane and finally washed with 2 M HCl. The organic phase was combined and dried with anhydrous MgSO4. Filtration and removal of the solvent under reduced pressure gave the crude product. The desired product was further purified by flash column chromatography with petroleum ether-EtOAc (20:1 to 10:1) to produce 6b1?6b20.

According to the analysis of related databases, 3-Trifluoromethoxyaniline, the application of this compound in the production field has become more and more popular.

Reference:
Article; Zhu, Kongkai; Song, Jia-Li; Tao, Hong-Rui; Cheng, Zhi-Qiang; Jiang, Cheng-Shi; Zhang, Hua; Bioorganic and Medicinal Chemistry Letters; vol. 28; 23-24; (2018); p. 3693 – 3699;,
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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 126-38-5 as follows. 126-38-5

To a solution of 4-bromopyridin-2-amine (1.08 g, 6.24 mmol) in H20 (20 mL) were added l-bromo-2,2-dimethoxypropane (5.59 g, 30.5 mmol) and 4-methylbenzenesulfonic acid (209.4 mg, 1.216 mmol). The reaction mixture was heated to reflux and stirred for 12 hours and then adjusted to pH = 10 with saturated Na2C03 aqueous solution, the resulting mixture was extracted with EtOAc (100 mL x 3). The combined organic layers were dried over anhydrous Na2S04, filtered and concentrated in vacuo. The residue was purified by silica gel column chromatography (PE/EtOAc(v/v) = 3/1) to give the title compound as a yellow solid (750 mg, yield 57%).MS (ESI, pos. ion) m/z: 211.1 [M+H]+.

According to the analysis of related databases, 126-38-5, the application of this compound in the production field has become more and more popular.

Reference:
Patent; SUNSHINE LAKE PHARMA CO., LTD.; CALITOR SCIENCES, LLC; XI, Ning; LI, Minxiong; PENG, Ju; LI, Xiaobo; ZHANG, Tao; HU, Haiyang; CHEN, Wuhong; BAI, Changlin; KE, Donghua; CHEN, Peng; (281 pag.)WO2019/99311; (2019); A1;,
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366-99-4, These common heterocyclic compound, 366-99-4, name is 3-Fluoro-4-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.

To cyanuric chloride(0. 368 g, 2 mmol) inCH3CN atabout-20 C was added3-fluoro-p-anisidine (0.28 g, 2 mmol) in CH3CN followed by the addition of DIEA (0.39mL, 2.2 mmol) and stirred for about1 hour. The reaction mixture was then stirred at room temperature for about1 hour. Then cyclopropylamine (1.39 mL, 20 mmol) and DIEA (0.39 mL, 2.2 mmol) were added and the reaction mixture was stirred overnight at rt. The reaction mixture was worked up as usual, diluted with ethyl acetate and washed with brine. The organic layer was separated and dried over sodium sulfate, filtered, concentrated under reduced pressure, and compound 157 was purified by silica gel column chromatography (200 mg,30percent), mp91-92 C ; HPLC : Inertsil ODS-3V C18, 40: 30: 30[KH2PO4(0. 01 M, pH3. 2):CH30H : CH3CN], 264nm, Rt 8.6 min, 99.1percent purity; MS(ESI) : m/z 331 (M+H, 100), 305 (0.8), 151 (. 3).

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 366-99-4.

Reference:
Patent; REDDY US THERAPEUTICS, INC.; WO2004/26844; (2004); 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. 2062-98-8, name is Perfluoro(2-methyl-3-oxahexanoyl) fluoride belongs to ethers-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below. 2062-98-8

Put 0.51 g (4.2 mmol) of 4-ethylphenol into a three-necked flask, add 20 mL of dichloromethane, and add 1.99 g (6 mmol) of hexafluoropropylene oxide dimer (CF3CF2CF2OCF (CF3 ) COF, provided by Zhejiang Huanxin Fluorine Materials Co., Ltd., recorded as FEOCOF), after the addition, add 0.05mL (0.0007mmol) N, N-dimethylformamide (DMF), and slowly add 0.4mL ( 0.003 mmol) dry triethylamine,After the dropwise addition was completed, the reaction was stirred at 40 C. for 2 h.After the reaction, 20 mL of deionized water was added and extracted with dichloromethane (20 mL ¡Á 3). The organic phases were combined and dried over MgSO 4, filtered, and rotary evaporated to obtain a crude product. The crude product was separated by silica gel column chromatography (eluted with petroleum ether). Agent) to obtain a colorless slightly viscous liquid, that is, the target product, with a yield of 99.1%.

The synthetic route of 2062-98-8 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Shaanxi Normal University; Yang Le; Chen Jiangang; Liu Zhaotie; Zhang Qiyu; Li Ruiqing; Shen Shukun; Liu Zhongwen; (11 pag.)CN110776426; (2020); A;,
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1579-40-4, The chemical industry reduces the impact on the environment during synthesis 1579-40-4, name is Di-p-tolyl Ether, I believe this compound will play a more active role in future production and life.

Representative Experimental Protocol: 2,7-Dimethyl-9-(4-nitro)phenyl xanthen-9-ol (R = NO2: 3e): Di-p-tolyl ether (1, 5 g, 25.5 mmol), 4-nitro benzoic acid (5.13 g, 30.7 mmol) and ZnCl2 (10 g, 73.4 mmol) are taken into a 100 ml double neck RB flask and charged with POCl3 (7.5 mL) and heated to 95 C for 4 h. The reaction mixture turned into a brown viscous mass that was difficult to stir. The reaction mixture was then cooled to room temperature and crushed ice was added slowly while keeping the low temperature. To the above mixture was added H2O (75 mL) and stirred for 12 h. The above reaction mixture was filtered and the residue was washed with H2O (20 mL) and hexane (20 mL) to afford 4-nitro-DMPx 3e as white powder. The crude product was dissolved in EtOAc and washed with NaHCO3 to remove the excess of 4-nitro benzoic acid. The EtOAc layer was evaporated under reduced pressure to furnish the desired product as fine powder 7.5 g (86%).

The chemical industry reduces the impact on the environment during synthesis Di-p-tolyl Ether. I believe this compound will play a more active role in future production and life.

Reference:
Article; Banerjee, Shyamapada; Srishylam; Rajendra Prasad; Migawa, Michael T.; Swayze, Eric E.; Sanghvi, Yogesh S.; Tetrahedron Letters; vol. 53; 35; (2012); p. 4669 – 4672;,
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