Ethers-buliding-blocks

Synthetic Route of 53087-13-1, 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. 53087-13-1, name is 1-(Benzyloxy)-3-bromobenzene belongs to ethers-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below.

A degassed mixture of 3-benzyloxy-phenyl bromide (28) (0.2 g, 0.76 mmol), 3- cyanophenylboronic acid (0.223 g, 1.52 mmol), barium hydroxide (0.285 g, 1.67 mmol), Pd(PPh3)4 (0.088 g, 0.076 mmol), DME (5 mL) and H2O (3 niL) was heated (80C) for 6 hours with vigorous stirring under an argon atmosphere. The reaction mixture was cooled to RT, diluted with ethyl acetate, and filtered through a plug of celite. The filtrate was diluted with brine; the organic phase was separated, dried (MgSO4), and concentrated in vacuo. The residue obtained was purified by flash column chromatography (20% diethyl ether-hexane) to give 75 (0.130 g, 60% yield) as a viscous liquid.[0411] 75 was confirmed as follows: 1H NMR (500 MHz, CDCl3) delta 7.85 (t, J = 2.5 Hz, 1H), 7.78 (dt, J = 7.5 Hz, J = 1.5 Hz, 1H), 7.63 (dt, J = 8.0 Hz, J = 1.5 Hz, 1H), 7.53 (t, J = 8.0 Hz, 1H), 7.46 (d, J = 7.5 Hz, 2H), 7.44-7.37 (m, 3H), 7.35 (t, J = 7.0 Hz, 1H), 7.18-7.14 (m, 2H), 7.02 (dd, J = 8.5 Hz, J = 2.5 Hz, 1H), 5.17 (s, 2H).

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, 1-(Benzyloxy)-3-bromobenzene, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; NORTHEASTERN UNIVERSITY; WO2009/52319; (2009); A1;,
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Reference of 7252-83-7, 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. 7252-83-7, name is 2-Bromo-1,1-dimethoxyethane belongs to ethers-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below.

A 100-mL, three-neck flask was charged with 2-bromo-l,l-dimethoxyethane 4 (23.2 g (16 mL, 137.2 mmol) and aqueous HBr (47.6% HBr by wt, 8.8 mmol/mL, 6.6 mL, 58.8 mmol), and the reaction mixture was heated to reflux (55C) for 2 hours. The mixture was allowed to cool to 40C, and solid NaHCC3 was added in small portions, until evolution of gas ceased. The resulting suspension was filtered, under vacuum, into a 500-mL, three-neck flask, and the filter cake was washed with isopropanol (200 mL). Solid 3,5-dibromopyrazin-2-amine (3) (12.0 g, 47.2 mmol) was added into the isopropanol filtrate, and the reaction mixture was heated at reflux (78C) for 16 hours. The resulting suspension was cooled to room temperature, filtered, the cake was washed with cold isopropanol (100 mL), and then the cake was dried under vacuum. The cake was transferred into a three-neck flask, into which, water (200 mL) was added, followed by solid K2CC3, in small portions, until gas evolution ceased, after which the reaction was stirred for 30 minutes. The resulting precipitate was isolated by filtration, and washed with water (200 mL). The solid was dried at 50C, to constant weight, then dissolved in THF, filtered through a plug (celite, silica gel, and charcoal). The solvent was removed under vacuum, to give 12.0 g of the desired product (5) as a white solid at 99% purity, as determined by NMR and LC-MS. IH NMR (500 MHz, CDC13) delta 8.26 (s, IH), 7.84 (d, J = 1.0 Hz, IH), 7.78 (d, J = 1.1 Hz, IH); 13C NMR (126 MHz, CDC13) delta 136.93, 134.06, 120.29, 119.26, 115.78.

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, 2-Bromo-1,1-dimethoxyethane, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; DOW GLOBAL TECHNOLOGIES LLC; ROHM AND HAAS ELECTRONIC MATERIALS KOREA LTD.; ONDARI, Mark E.; WELSH, Dean M.; FROESE, Robert DJ; NA, Hong-Yeop; (38 pag.)WO2016/209895; (2016); A1;,
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Related Products of 102503-23-1, 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 102503-23-1 as follows.

Reference Example 60; 1- (2, 4-dimethoxyphenyl) -N- { [4-fluoro-5- (2-fluoropyridin-3-yl) – lH-pyrrol-3-yl]methyl }-N-methylmethanamine; Sodium hydride (60% in oil, 2.23 g) was washed twice with hexane and suspended in tetrahydrofuran (180 mL) . To the suspension was added dropwise a solution of l-(2,4- dimethoxyphenyl) -N-methylmethanamine (9.09 g) in tetrahydrofuran (10 mL) at 0C. After the completion of the dropwise addition, the mixture was stirred at 600C for 18 hr. The reaction mixture was cooled to 0C, a solution of 3- (4, 4- difluoro-3-methylene-3, 4-dihydro-2H-pyrrol-5-yl) -2- fluoropyridine (9.64 g) in tetrahydrofuran (10 mL) was added dropwise, and the mixture was stirred at the same temperature for 1 hr. Ice water and saturated brine were added, and the mixture was extracted with ethyl acetate. The extract was washed successively with saturated aqueous ammonium chloride solution, saturated aqueous sodium hydrogen carbonate solution, water and saturated brine, dried over anhydrous sodium sulfate, and concentrated under reduced pressure. The residue was purified by basic silica gel column chromatography (eluent: ethyl acetate) to give the title compound as a yellow oil (yield 16.8 g, 97%) . 1H-NMR (CDCl3) delta: 2.24(3H,s), 3.51(2H,s), 3.54(2H,s), 3.79(3H,s), 3.80(3H,s), 6.45(lH,s), 6.42-6.50 (IH,m) , 6.68(lH,dd, J=4.7,3.6Hz) , 7.18-7.29 (2H,m) ,7.98 ( IH, ddd, J=4.5, 1.9, 1.5Hz) , 8.25 (IH, ddd, J=IO .2 , 8.0, 1.9Hz) , 8.67(1HzS) .

According to the analysis of related databases, 102503-23-1, the application of this compound in the production field has become more and more popular.

Reference:
Patent; TAKEDA PHARMACEUTICAL COMPANY LIMITED; WO2008/108380; (2008); A2;,
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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. 136-90-3, name is 4-Methoxy-3-methylphenylamine, This compound has unique chemical properties. The synthetic route is as follows., HPLC of Formula: C8H11NO

General procedure: 4-amino-6-chloropyrimidine (200 mg, 1.54 mmol) and KI(127.82 mg, 0.77 mmol) was dissolved in ethanol (35 mL). Trifluoroaceticacid (200 mL) was added after stirring and heating10 min for activating pyrimidine. Then to a stirred solution ofsubstituted aniline (1.23 mmol) in ethanol (15 mL) was added byway of drip for 1 h. The resulting mixture was heated to reflux for36 h, allowed to cool to room temperature, and concentrated invacuo. Then the solid residue was diluted with ethyl acetate and asaturated aqueous solution of NaHCO3. The aqueous layer wasseparated and extracted with ethyl acetate. The organic phase waswashed with brine, dried (Na2SO4), filtered, and concentrated. Purificationof the crude product by silica gel column chromatography(ethyl acetate/light petroleum, 2:1 and 1:1), provided the desiredproduct (batch1). Substituted aniline (2,6-dichloro and 3,5-dimethoxy) (200 mg) was dissolved in CH2Cl2 (15 mL) was addedby way of drip phosgene which dissolved in CH2Cl2 (20 mL)(batch1/phosgene, 2:1 (mol)) at 0 C for 0.5 h. The resulting mixturewas heated to reflux for 3e6 h, allowed to cool to room temperature,and concentrated in vacuo. Then the solid residue was dilutedwith ethyl acetate and a saturated aqueous solution of NaHCO3. Theaqueous layer was separated and extracted with ethyl acetate. Theorganic phase was washed with brine, dried (Na2SO4), filtered, andconcentrated. Purification of the crude product by silica gel columnchromatography (CH2Cl2/MeOH/aqueous NH3, 96:3:1), providedthe desired product (batch2). Batch1 and batch2 (batch1/batch2,5:6 (mol)) were dissolved in toluene (10 mL,18.89 mmol), theresulting mixture was heated to reflux for 8e10 h, allowed to coolto room temperature, then filtered by toluene to provide the endproduct(the residue).

According to the analysis of related databases, 136-90-3, the application of this compound in the production field has become more and more popular.

Reference:
Article; Xie, Zixin; Wu, Kaiqi; Wang, Yuexuan; Pan, Yaqian; Chen, Bo; Cheng, Donghua; Pan, Suwei; Guo, Taoning; Du, Xuze; Fang, Longcheng; Wang, Xuebao; Ye, Faqing; European Journal of Medicinal Chemistry; vol. 187; (2020);,
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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. 39021-83-5, name is 1,4-Dimethoxy-2,3-dimethylbenzene, A new synthetic method of this compound is introduced below., Safety of 1,4-Dimethoxy-2,3-dimethylbenzene

To a solution of 1,4-dimethoxy-2,3-dimethylbenzene (5 g, 30 mmol) in acetic acid (350 ml) was added bromine (1.54 ml, 30 mmol). After stirring for 10 min the mixture was quenched with aqueous bisulphate and extracted into ether (3¡Á50 ml). The organic layer was dried with magnesium sulfate and then the solvent removed under reduced pressure

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; Bedford, Robin B.; Bowen, John G.; Weeks, Amanda L.; Tetrahedron; vol. 69; 22; (2013); p. 4389 – 4394;,
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Synthetic Route of 104197-14-0, 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. 104197-14-0 name is 4-Bromo-2,6-difluoroanisole, 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.

[0241] Step a: Lithium diisopropylamine solution in THF (1 M, 25 mL, 25 mmol) was added slowly to a solution of 5-bromo-1,3-difluoro-2-methoxybenzene (4.5 g, 20.2 mmol) in anhydrous THF (50 mL) under N2 and vigorously stirred at 78 C. The reaction mixture was stirred at 60 C for 1 h, followed by rapid addition of DMF (5 mL). The reaction mixture was stirred at the same temperature and allowed to warm to 50 C over 1 h. The reaction was poured into a mixture of ice (200 g), concentrated hydrochloric acid (20 mL) and MTBE (100 mL) and the mixture was stirred and allowed to warm up to room temperature over 2 h. The oranic layer was separated, washed with brine and dried over MgSO4. The solvent was removed under reduced pressure to give 6-bromo-2,4-difluoro-3-methoxybenzaldehyde . MS: (ES) m/z calculated for C8H6BrF2O2 [M + H]+ 250.9, found 250.9.

At the same time, in my other blogs, there are other synthetic methods of this type of compound, 4-Bromo-2,6-difluoroanisole, and friends who are interested can also refer to it.

Reference:
Patent; CHEMOCENTRYX, INC.; FAN, Pingchen; LANGE, Christopher W.; LUI, Rebecca M.; MALATHONG, Viengkham; MALI, Venkat Reddy; PUNNA, Sreenivas; SINGH, Rajinder; TANAKA, Hiroko; ZENG, Yibin; ZHANG, Penglie; (284 pag.)WO2018/222598; (2018); A1;,
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Reference of 651734-54-2, 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. 651734-54-2, name is 2,6-Difluoro-3,5-dimethoxyaniline belongs to ethers-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below.

To a stirred slurry of 2,6-difluoro-3,5-dimethoxyaniline (1.00 g, 5.29 mmol) in 6.0 M hydrogen chloride in water (9.00 mL, 54.0 mmol), a solution of sodium nitrite (0.383 g, 5.55 mmol) in water (2 mL) was added dropwise over 15 minutes at 0 C. After another 15 minutes, the resulting orange-red slurry was added to a solution of potassium iodide (3.50 g, 21.1 mmol) in water (5 mL) in small portions at 0 C. After addition, the reaction mixture was allowed to warm to room temperature and then it was stirred for 1 hout Solid precipitated which was filtered out. The solid was washed with water and dried under vacuum to give the desired product (1.15 g, 70%). 1H NMR (400 MHz, CDCl3): delta 6.68 (t, J=8.0 Hz, 1H), 3.88 (s, 6H) ppm.

The synthetic route of 2,6-Difluoro-3,5-dimethoxyaniline has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Incyte Corporation; Lu, Liang; He, Chunhong; Yao, Wenqing; US2014/45814; (2014); A1;,
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Related Products of 53087-13-1, The chemical industry reduces the impact on the environment during synthesis 53087-13-1, name is 1-(Benzyloxy)-3-bromobenzene, I believe this compound will play a more active role in future production and life.

The (2S,4R)-4-(3-hydroxyphenyl)-4-methoxy-2-methyltetrahydropyran, used as a starting material, was obtained as follows: A Grignard reagent was prepared by heating a mixture of 3-benzyloxybromobenzene (4.2 g), magnesium (0.4 g), and tetrahydrofuran (10 ml) to reflux for 30 minutes. The mixture was allowed to cool to approximately 40 C. and a solution of (2S)-2-methyltetrahydropyran-4-one (1.55 g) in tetrahydrofuran (7 ml) was added dropwise. The mixture was stirred and warmed to 40 C. for 3 hours. The mixture was partitioned between ethyl acetate and cold dilute aqueous hydrochloric acid solution. The organic phase was washed with a saturated aqueous sodium chloride solution, dried (MgSO4) and evaporated. The residue was purified by column chromatography using a 10:3 v/v mixture of toluene and ethyl acetate as eluent. There was thus obtained, as a mixture of diastereoisomers, (2S,4R)- and (2S,4S)-4-(3-benzyloxyphenyl)-4-hydroxy-2-methyltetrahydropyran (3.71 g, 92%), as an oil, which was partly separated to give a fraction (2.33 g) which was enriched in the less polar diastereoisomer. Sodium hydride (55% w/w dispersion in mineral oil, 0.39 g) was added to a solution of the enriched fraction so obtained (2.33 g) in dimethylformamide (16 ml) which had been cooled to -5 C. and the mixture was stirred at this temperature for 1 hour. Methyl iodide (0.61 ml) was added and the mixture was stirred for 2 hours and allowed to warm to ambient temperature. The mixture was partitioned between ethyl acetate and ice-cold water. The organic phase was washed with a saturated aqueous sodium chloride solution, dried (MgSO4) and evaporated. The residue was purified by column chromatography using a 20:1 v/v mixture of toluene and ethyl acetate as eluent. There was thus obtained (2S,4R)-4-(3-benzyloxyphenyl)-4-methoxy-2-methyltetrahydropyran (1.99 g, 82%), as an oil. NMR Spectrum: (CDCl3, delta values) 1.2(d, 3H), 1.5-1.65(m, 1H), 1.9-2.05(m, 3H), 2.96(s, 3H), 3.8-4.0(m, 3H), 5.1(s, 2H), 6.85-7.05(m, 3H), 7.2-7.5(m, 6H).

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, 1-(Benzyloxy)-3-bromobenzene, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; Imperial Chemical Industries PLC; ICI Pharma; US5134148; (1992); A;,
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Adding a certain compound to certain chemical reactions, such as: 1535-73-5, name is 3-Trifluoromethoxyaniline, 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 1535-73-5, COA of Formula: C7H6F3NO

Pentafluorophenyl chlorothionoformate (2.89 mL, 18.01 mmol) in DCM (10 mL) was added dropwise to 3-(Trifluoromethoxy)aniline (2.189 mL, 16.37 mmol) and Pyridine (1.986 mL, 24.56 mmol) in dichloromethane (180 mL) at O0C. The resulting solution was stirred at ambient temperature for 20 hours. The reaction mixture was washed sequentially with IM citric acid (100 mL), saturated NaHCCbeta (100 mL), and saturated brine (100 mL). The organic layer was dried over MgSO4, filtered and evaporated to afford crude product. The crude product was purified by flash silica chromatography, elution gradient 5 to 15percent ethyl acetate in isohexane. Pure fractions were evaporated to dryness to afford O- perfiuorophenyl 3-(trifluoromethoxy)phenylcarbamothioate (3.70 g, 56.0percent) as a yellow oil. IH NMR (400 MHz, CDC13) delta 7.08 (IH, s), 7.13 – 7.19 (2H, m), 7.38 (IH, t).

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; ASTRAZENECA AB; ASTRAZENECA UK LIMITED; WO2009/24821; (2009); A2;,
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Related Products of 5961-59-1, These common heterocyclic compound, 5961-59-1, name is 4-Methoxy-N-methylaniline, 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.

HATU (1.5 g, 4.0 mmol) was added to a stirred solution of 4-methoxy-N- methylaniline (500 mg, 3.64 mmol) and (S)-2-((tert-butoxycarbonyl)amino)-3-phenylpropanoic acid (1.06 g, 4.0 mmol) in DMF (20 mL) and DIPEA (1.3 mL, 7.3 mmol) and the reaction mixture was stirred at RT for 4h. The reaction was concentrated and the residual crude oil was partitioned between EtOAc (60 mL) and 1/2 sat. NaHCO3 (aq) (60 mL). The organic component was washed with brine (40 mL), dried (Mg504), filtered, concentrated and purified using a Biotage Horizon (80g5i02, 10-40% EtOAc/hexanes) to yield (5)-tert-butyl (1-((4- methoxyphenyl)(methyl)amino)- 1 -oxo-3 -phenylpropan-2-yl)carbamate (1.34 g) as a clear amber viscous oil. LC-MS retention time = 3.17 mm; mlz = 385.3 [M+H]. (Column: Phenonenex-Luna C18 2.0 x 50mm 3 pm. Solvent A = 95% Water:5% Acetonitrile:10 miVi NH4OAc. Solvent B = 5% Water:95% Acetonitrile:10 miViNH4QAc. Flow Rate = 0.8 mL/min. Start % B = 0. Final % B = 100. Gradient Time= 4 mm. Wavelength = 220). ?H NMR (400MHz, CDC13) oe 7.25 – 7.20 (m, 3H),7.03 – 6.64 (m, 6H), 5.20 (d, J=8.8 Hz, 1H), 4.53 (q, J=7.4 Hz, 1H), 3.83 (s, 3H),3.18 (s, 3H), 2.89 (dd, J=13.1, 7.5 Hz, 1H), 2.71 (dd, J=13.1, 6.5 Hz, 1H), 1.39 (s,9H).

The synthetic route of 5961-59-1 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; BRISTOL-MYERS SQUIBB COMPANY; PENDRI, Annapurna; LI, Guo; BENDER, John A.; YANG, Zhong; WANG, Alan Xiangdong; BENO, Brett R.; FRIDELL, Robert A.; BELEMA, Makonen; MEANWELL, Nicholas A.; GENTLES, Robert G.; WO2015/61518; (2015); A1;,
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