Author: Jessica.F

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;,
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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;,
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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;,
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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. 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;,
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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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Application of 24743-14-4, 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. 24743-14-4 name is 3-(3-Methoxyphenyl)-1-propene, 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.

1-Allyl-3-methoxybenzene (prepared in accordance with the reference [Journal of Organic Chemistry, 2013, vol. 78, p.9772-9780]; 2.44 g, 16.5 mmol) was dissolved in THF (19 mL), slowly added with 9-BBN (0.5M THF solution, 39.5 mL, 19.8 mmol), and stirred at room temperature for 2 hours. The reaction mixture was added with the compound obtained in (6.5 g, 18.1 mmol), K2CO3 (6.83 g, 49.3 mmol) and DMF (38mL), and then substituted with nitrogen. Subsequently, the mixture was added with [1,1′-bis(diphenylphosphino)ferrocene]dichloropalladium(II) complex with dichloromethane (672 mg, 0.823 mmol), and then stirred at 110C for 15 hours. The reaction mixture was cooled to room temperature, added with a saturated NH4Cl aqueous solution, and extracted with EtOAc. The organic layer was washed with brine, dried over sodium sulfate, filtered and concentrated under reduced pressure. The residue thus obtained was purified by silica gel chromatography to obtain the title compound (colorless oil, 3.49 g, 55% yield). (1343) 1H NMR (600 MHz, CDCl3) delta 8.09 (d, 1H), 7.21 (t, 1H), 7.00 (d, 1H), 6.79 (d, 1H), 6.76 – 6.74 (m, 2H), 3.92 (s, 3H), 3.80 (s, 3H), 2.76 (dd, 2H), 2.68 (t, 2H), 1.98 – 1.93 (m, 2H).

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

Reference:
Patent; SK Chemicals Co., Ltd.; LEE, Ju Young; LEE, Jeong A; AHN, Jaeseung; RYU, Je Ho; HAN, Min-Young; YOO, Taekyung; SA, Joon Ho; KIM, Jae-Sun; (297 pag.)EP2963027; (2016); 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. 2062-98-8, name is Perfluoro(2-methyl-3-oxahexanoyl) fluoride, A new synthetic method of this compound is introduced below., Computed Properties of C6F12O2

A mixture of ethanolamine (13 g, 28 mmol) and ether (30 mL) was cooled to 15C. Perfluoro-2-methyl-3-oxahexanoyl fluoride (33 g in ether 50 mL) was added dropwise to keep the reaction temperature below 25C. After the addition, the reaction mixture was stirred at room temperature for one hour. The solid was removed by filtration and the filtrate was washed with hydrochloric acid (0.5N, 30 mL), water (2 times 30 mL), sodium hydrogen carbonate solution (0.5N, 20 mL), water (30 mL), and sodium chloride solution (saturated, 20 mL). It was then concentrated and dried in vacuum over night at room temperature to give a white solid 35 g, yield 95%. The product was analyzed using ^HNMR and the structure confirmed as is N-(perfluoro-2-methyl-3-oxahexanoyl)-2-aminoethanol, C3F7OCF(CF3)CONHCH2CH2OH.

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; E. I. DU PONT DE NEMOURS AND COMPANY; MURPHY, Peter, Michael; HEWAT, Tracy; WO2010/2623; (2010); A2;,
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Application of 366-99-4, 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. 366-99-4, name is 3-Fluoro-4-methoxyaniline belongs to ethers-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below.

Acetic anhydride (159 mmol, 1 .495 eq) is added to 3-fluoro-4-methoxyaniline (106 mmol, 1 eq) at RT and the resulting mixture is stirred at this temperature for 30 minutes. Nitric acid (156 mmol, 1.57 eq) is then added dropwise and the resulting suspension is stirred at RT for 3 h. Water is added to quench the reaction, the resulting solid collected by filtration and dried under vacuum. A/-(5-Fluoro-4-methoxy-2-nitrophenyl)acetamide (24.2 g) is obtained as a yellow solid. LC-MS (conditions F): tR = 0.71 min, [M + 1 + CH3CN]+ = 270.25.

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

Reference:
Patent; ACTELION PHARMACEUTICALS LTD; BOSS, Christoph; BROTSCHI, Christine; HEIDMANN, Bibia; SIFFERLEN, Thierry; WILLIAMS, Jodi T.; WO2012/85857; (2012); 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. 437-82-1, name is 2,6-Difluoroanisole belongs to ethers-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below. Quality Control of 2,6-Difluoroanisole

500 ml dry reaction flask, replaced with nitrogen gas, was added the compound (IV) 28.8 g of 100 ml of anhydrous 2-methyltetrahydrofuran, in the system under a nitrogen atmosphere, stirred and cooled to -78C, and slowly added dropwise 1.6M n-hexane solution of n-butyllithium in 185 ml. after completion of the dropwise addition, at -60 ~ -50C reaction was stirred for 2 hours.System cooling to -78C, carbon dioxide gas through for 5 hours after completion through ~ -40 -30C was stirred for 3 hours.The reaction system was allowed to warm to room temperature, 200 ml of water, stirred, and the organic solvent is recovered by distillation under reduced pressure, and the residue with 36% hydrochloric acid, filtered, and the filter cake washed with 100 ml of water, dried to give compound (V) 31.6 g.

The synthetic route of 437-82-1 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; ZHEJIANG ZHONGXIN FU CAI CO LTD/ ZHEJIANG ZHONGXIN CHEMICALS CO., LTD.; YUAN, QILIANG; ZHANG, JIABING; XU, PENGFEI; JIANG, XIANBO; CHEN, YINHAO; WANG, CHAO; (16 pag.)CN103819401; (2016); B;,
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