Month: June 2021

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. 1077-01-6, name is 1-Fluoro-3-(trifluoromethoxy)benzene belongs to ethers-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below. Quality Control of 1-Fluoro-3-(trifluoromethoxy)benzene

(Comparative Example 6); 4-Fluoro-l-nitro-2- (trifluoromethoxy) benzeneFuming nitric acid (20 mL) was added dropwise to concentrated sulfuric acid (40 ml) under cooling (-100C), and subsequently, 1- fluoro-3- (trifluoromethoxy) benzene (15 g, 83 mmol) was added to the mixture at -100C, and the mixture was stirred for 0.5 hours. After the mixture was added into ice-water to stop the reaction, it was extracted with dichloromethane . After the obtained organic layer was washed with a IN aqueous sodium hydroxide solution and water, it was dried with anhydrous sodium sulfate. After filtration, the solution was concentrated and the residue was purified by silica gel column chromatography (100:0-97:3, hexane : ethyl acetate) to give the title compound (3.1 g, 16%) as an oil.1H-NMR (400 MHz, CDCl3) delta: 8.10 (IH, dd, J = 5.5, 9.4 Hz) , 7.23-7.15 (2H, m) .

The synthetic route of 1077-01-6 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; EXELIXIS, INC.; Daiichi Sankyo Company, Limited; NUSS, John; WILLIAMS, Matthew; MOHAN, Raju; MARTIN, Richard; WANG, Tie-lin; TSURUOKA, Hiroyuki; AOKI, Kazumasa; HONZUMI, Masatoshi; ASOH, Yusuke; SAITO, Keiji; HOMMA, Tsuyoshi; WO2010/42626; (2010); A1;,
Ether – Wikipedia,
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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. 171290-52-1, name is 3,5-Dimethoxyphenylacetylene, A new synthetic method of this compound is introduced below., COA of Formula: C10H10O2

Formula 7 of the azide compound (300 mumol), alkynyl (750 mumol), CuSO4 (9.6 mg, 60 mumol) and Na. An ascorbate (60.0 mg, 300 mumol) 1: was dissolved in 1 t-BuOH / H2O (3 mL). The mixture was stirred at room temperature for 2 hours. After the reaction was completed, the mixture was filtered of and washed using H2O (70 mL) (solid A). The filtrate was extracted with EtOAc (3 × 70 mL). The combined organic extracts were then dried using anhydrous MgSO4, filtered and concentrated by rotaryevaporation (residue B). It was combined and the solid residue A and B, was purified by column chromatography to give the compound of formula 2 and 3. Following the general method for the general formula 2, 1: 1 t-BuOH / H2O (1 mL) Compound 7g (31.2 mg, 100 mumol), in a 1-Ethynyl -3,5-dimethoxy-benzene (40.5 mg, 250 mumol), CuSO4 (3.2 mg, 20 mumol) and Na. Using ascorbate (20.0 mg, 100mumol) was prepared the desired compound. After stirring at 60 the reaction mixture for 5 hours, was purified by column chromatography (5: 1 hexane / EtOAc ? 20: 1 CH2Cl2 / MeOH) using afford 2g as a brown solid (33,6mg, 71% ).

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; EWHA UNIVERSITY INDUSTRY-ACADEMIC COOPERATION FOUNDATION; YOO, JAE SANG; SONG, DOO HUI; (33 pag.)KR2015/134731; (2015); A;,
Ether – Wikipedia,
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Synthetic Route of 59557-91-4,Some common heterocyclic compound, 59557-91-4, name is 4-Bromo-2-methoxyaniline, molecular formula is C7H8BrNO, 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.

4-Bromo-2-methoxyaniline (50.0 g, 247 mmol) was added to a mixture of sodium 3- nitrobenzenesulfonate (86.8 g, 385 mmol) and propane-1 ,2,3-triol (108 g, 1 .18 mol) in cone. H2SO4 (97 ml.) and water (75.7 ml.) at 0 C over a period of 30 min under nitrogen. After stirring at 120 C for 24 h and then cooling to RT, the reaction mixture was quenched slowly with 2M NaOH (1 L). The aq. solution was extracted with EtOAc (3 x 500 ml_). The combined organic phases were dried over Na2S04, filtered and concentrated to afford 6-bromo-8- methoxyquinoline (Intermediate 49, 60.0 g, 100%); M/Z (ES+), [M+H]+= 237.1H NMR (300 MHz, DMSO-ofe) delta 3.99 (s, 3H), 7.30 (d, 1 H), 7.58-7.60 (m, 1 H), 7.79 (s, 1 H), 8.28 (dd, 1 H), 8.86 (dd, 1 H).

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

Reference:
Patent; ASTRAZENECA AB; PACKER, Martin, John; PERKINS, David, Robert; SWALLOW, Steven; HIRD, Alexander; YE, Qing; PENG, Bo; ZHENG, Xiaolan; JOHANNES, Jeffrey; MLYNARSKI, Scott; LAMB, Michelle; HUYNH, Hoan; ROBBINS, Daniel, William; (182 pag.)WO2018/178226; (2018); A1;,
Ether – Wikipedia,
Ether | (C2H5)2O – PubChem

Application of 52189-63-6, 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. 52189-63-6 name is 1-Fluoro-3,5-dimethoxybenzene, 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.

Step 4: Intermediate 5-f: To a solution of 1-fiuoro-3,5-dimethoxybenzene (12.5 g, 80 mmol) in dichloromethane (80 ml) cooled to 0C was added dropwise over a period of 30 minutes a 1.0 M solution of BBr3 in dichloromethane (200 ml, 200 mmol). The reaction was stirred for 1 hour at 0C and then slowly warmed to room temperature and stirred for 18 hours. The reaction was cooled to 0C and quenched by slow addition of MeOH and water. After stirring at room temperature for 1 hour the mixture was filtered and volatiles were removed under reduced pressure. Ethyl acetate was added to the residue; a precipitate formed and was collected by filtration to provide intermediate 5-f as orange solid

At the same time, in my other blogs, there are other synthetic methods of this type of compound, 1-Fluoro-3,5-dimethoxybenzene, and friends who are interested can also refer to it.

Reference:
Patent; PHARMASCIENCE, INC.; LAURENT, Alain; ROSE, Yannick; WO2014/29007; (2014); A1;,
Ether – Wikipedia,
Ether | (C2H5)2O – PubChem

Application of 5467-58-3,Some common heterocyclic compound, 5467-58-3, name is 1-Bromo-4-methoxynaphthalene, molecular formula is C11H9BrO, 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.

4-a. Synthesis of 1-methoxy-4-{4-(naphthalen-2-yl)phenyl}naphthalene 1-Methoxy-4-{4-(naphthalen-2-yl)phenyl} was synthesized as follows. 1-Bromo-4-methoxynaphthalene (25 g, 0.105 mol), 4-(naphthalen-2-yl)phenylboronic acid (30.4 g, 0.137 mol), potassium carbonate (21.9 g, 0.16 mol), tetrakis(triphenylphosphine)palladium(0) (2.4 g, 0.01 mol), water (25 mL), tetrahydrofuran (75 mL) and toluene (75 mL) were stirred in a 250 mL round-bottom flask for 12 hours under reflux. After completion of the reaction, the reaction mixture was cooled to room temperature and extracted with ethyl acetate (300 mL) and water (1000 mL). The organic layer was dried with magnesium sulfate and concentrated under reduced pressure. The resulting solid was dissolved in hot toluene (400 mL) and filtered. The filtrate was recrystallized in methanol (800 mL). The resultant solid was filtered and washed with hexane (300 mL) to obtain a product (26 g, 0.072 mol, 68.4%).

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

Reference:
Patent; SFC CO., LTD.; US2011/108827; (2011); A1;,
Ether – Wikipedia,
Ether | (C2H5)2O – PubChem

Reference of 82830-49-7, The chemical industry reduces the impact on the environment during synthesis 82830-49-7, name is 2-Fluoro-1,4-dimethoxybenzene, I believe this compound will play a more active role in future production and life.

To a stirred solution of 2-fluoro-l,4-dimethoxybenzene (500 mg, 3.2 rnmol) in THF (10 mL) at -78 0C was added dropwise a 2.5M solution of n-BuLi in hexane (1.28 mL, 3.2 mmol). The reaction mixtured was stirred for Ih, and then DMF (0.27 mL, 3.5 mmol) was added at such a rate as to keep the temperature below -70 0C. Upon completion of addition, the reaction mixture was stirred for 3h and then quenched at -78 by addition of a solution of acetic acid (“HOAc”) in THF. Water was added and the reaction mixture was extracted with ethyl acetate. The organic extracts were dried over MgSO4, filtered, and the solvent was removed under reduced pressure to provide Intermediate 20 as a yellow solid (518 mg, 88%), which was used without further purification.

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-Fluoro-1,4-dimethoxybenzene, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; BRISTOL-MYERS SQUIBB COMPANY; WO2007/30582; (2007); A2;,
Ether – Wikipedia,
Ether | (C2H5)2O – PubChem

Electric Literature of 332-48-9,Some common heterocyclic compound, 332-48-9, name is 1-(2-Bromoethoxy)-4-fluorobenzene, molecular formula is C8H8BrFO, 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 flask containing tetrahydrofuran (5.0 niL) was charged with sodium amide (109 mg, 2.65 mmol; Alfa Aesar), chilled to 0 0C, and treated with 2,1 l-dimethyl-5,6,7,8,9,10- hexahydro-7,10-epiminocyclohepta[delta]indole (300 mg, 1.326 mmol; Example IA), added in portions. After 5 minutes, the ice bath was removed and the mixture was heated to 60 0C for 15 minutes. The solution was cooled to room temperature and l-(2-bromoethoxy)-4- fluorobenzene (348 mg, 1.591 mmol; Aldrich) was added slowly. The reaction mixture was stirred overnight at room temperature, then diluted with water (5 mL) and extracted with dichloromethane (2×10 mL). The combined organic extracts were dried over magnesium sulfate, filtered, concentrated in vacuo, and the resulting residue was purified by reverse- phase HPLC (Phenomenex Luna C8(2) 5 mum IOOA AXIA column, 30×75 mm, 10-95% gradient of acetonitrile in 0.1% aqueous trifluoroacetic acid, flow rate 50 mL/minute) to afford the title compound as the trifluoroacetic acid salt: 1H NMR (300 MHz, methanol-^) delta ppm 1.79 – 2.07 (m, 1 H), 2.12 – 2.30 (m, 1 H), 2.34 – 2.50 (m, 4 H), 2.50 – 2.66 (m, 1 H), 2.93 (s, 3 H), 3.02 – 3.20 (m, 1 H), 3.66 (d, J=17.1 Hz, 1 H), 4.13 – 4.37 (m, 3 H), 4.42 – 4.58 (m, 2 H), 4.93 – 5.12 (m, 1 H), 6.61 – 6.84 (m, 2 H), 6.81 – 7.01 (m, 2 H), 7.01 – 7.14 (m, 1 H), 7.31 (s, 1 H), 7.34 – 7.43 (m, 1 H); MS (ESI) m/z 365 (M+H)+.

The synthetic route of 332-48-9 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; ABBOTT LABORATORIES; SCHRIMPF, Michael R.; LEE, Chih-Hung; LI, Tao; GFESSER, Gregory A.; MORTELL, Kathleen H.; FAGHIH, Ramin; NERSESIAN, Diana L.; SIPPY, Kevin B.; BUNNELLE, William H.; SCANIO, Marc; SHI, Lei; GOPALAKRISHNAN, Murali; DONNELLY-ROBERTS, Diana; HU, Min; WO2010/36998; (2010); A2;,
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Reference of 4342-46-5, The chemical industry reduces the impact on the environment during synthesis 4342-46-5, name is 4-Methoxycyclohexanamine, I believe this compound will play a more active role in future production and life.

General procedure: To a solution of 7a-d (1.0 equiv.) and amine (2.0 equiv.) in dioxane was added glacial acetic acid (0.2 equiv.), then the mixture was stirred and heated at 110 C in a sealed tube for 10-20 h. The mixture was concentrated under vacuum, and the residue was purified by column chromatography on silica gel, using petroleum ether/ethyl acetate to afford target products 8-25.

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, 4-Methoxycyclohexanamine, other downstream synthetic routes, hurry up and to see.

Reference:
Article; Zhang, Dongfeng; Liu, Yang; Zhang, Chunlin; Zhang, Hao; Wang, Bin; Xu, Jian; Fu, Lei; Yin, Dali; Cooper, Christopher B.; Ma, Zhenkun; Lu, Yu; Huang, Haihong; Molecules; vol. 19; 4; (2014); p. 4380 – 4394;,
Ether – Wikipedia,
Ether | (C2H5)2O – PubChem

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. 1484-26-0, name is 3-Benzyloxyaniline, This compound has unique chemical properties. The synthetic route is as follows., Product Details of 1484-26-0

A suspension of 2-chloro-5-bromopyrimidine (300 mg, 1.55 mol), 3-benzyloxyaniline (680 mg, 3.41 mmol), tpi’5′(dibenzylideneacetone)palladium(0) (56 mg, 61.1 mumol), 4,5-fos(diphenylphosphino)-9,9-dimethylxanthene (71 mg, 122.7 mumol) and cesium carbonate (1.21 g, 3.72 mmol) in degassed 1,4-dioxan (7 mL) was heated at 80°C for 4 days. After cooling to room temperature, the mixture was diluted with ethyl acetate and washed with water, 0.5 M hydrochloric acid and brine. The organic phase was dried (MgSO4) and the solvent removed under reduced pressure to give a thick orange- brown oil. The crude product was purified by column chromatography on silica gel eluting with 1:3 ethyl acetate/petroleum ether to afford the title compound as an off- white solid (203 mg, 28 percent). deltaH (4-DMSO, 400 MHz): 5.08 (2 H, s), 5.10 (2 H, s), 6.42-6.50 (3 H, m), 6.58 (1 H, d), 7.11 (1 H, t), 7.20 (1 H, t), 7.30-7.50 (11 H, m), 7.62 (1 H, s), 7.91 (1 H, s), 8.38 (2 H, s) and 9.53 (1 H, s).LCMS (ES+): 475 (MH+, 100 percent).

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 1484-26-0.

Reference:
Patent; SENEXIS LIMITED; WO2007/125351; (2007); A1;,
Ether – Wikipedia,
Ether | (C2H5)2O – PubChem

Synthetic Route of 886762-08-9, The chemical industry reduces the impact on the environment during synthesis 886762-08-9, name is 5-Bromo-2-(trifluoromethoxy)aniline, I believe this compound will play a more active role in future production and life.

General procedure: Triphosgene (0.74 g, 2.5 mmol) was dissolved in anhydrousCH2Cl2 (20 mL) and the mixture was stirred on the ice-bath for15 min. A solution of the [3-bromo-5-(trifluoromethyl)phenyl]amine (1.66 g, 6.9 mmol) in anhydrous CH2Cl2 (10 mL) was addeddropwise to the above mixture and stirring continued for 30 min.Then triethanolamine (0.75 mL, 5.5 mmol) diluted with CH2Cl2(10 mL) was then added into the mixture. Stirring was continuedfor 20 min, a solution of triethanolamine (0.75 mL, 5.5 mmol) andintermediate (4a) (1.50 g, 6.3 mmol) in anhydrous CH2Cl2 (10 mL)was added. After completion of the action, the reaction wasquenched with dilute NaHCO3. The organic layer was washed withwater and brine, and dried over Na2SO4. After filtration and concentrationin vacuo, the residues was purified by silica gel flash chromatography (PE/AcOEt 5:1) gave as white solid (5a) (1.36 g,43%).

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, 5-Bromo-2-(trifluoromethoxy)aniline, other downstream synthetic routes, hurry up and to see.

Reference:
Article; Shan, Yuanyuan; Gao, Hongping; Shao, Xiaowei; Wang, Jinfeng; Pan, Xiaoyan; Zhang, Jie; European Journal of Medicinal Chemistry; vol. 103; (2015); p. 80 – 90;,
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