Month: June 2021

Reference of 27060-75-9, 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. 27060-75-9, name is 1-Bromo-4-methoxy-2-methylbenzene belongs to ethers-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below.

A dry, stir bar-equipped, 3-neck 250 mL round bottom flask was fitted with a reflux condenser and put under nitrogen. 77 1-bromo-4-methoxy-2-methylbenzene (1.39 mL, 2.011 g, 10.0 mmol, 1.00 eq), 121 CCl4 (20.0 mL, 0.50 Molar, not degassed), 122 N-bromosuccinimide (recrystallized, 2.67 g, 15.0 mmol, 1.50 eq), and 123 benzoyl peroxide (0.121 g, 0.50 mmol, 5 mol %) were added by briefly removing a septum while under positive nitrogen pressure. The reaction was heated to reflux for 18 hours. (0187) The next day, the reaction was filtered through a silica gel plug, rinsing with 10/1 Hex/Et2O. The crude product was purified by normal phase column chromatography (5 cm diameter, 300 mL silica gel, isocratic 4/1 Hex/DCM), giving SI-3 as a fluffy, slightly off-white powder (1.404 g, 5.015 mmol, 50% yield). (0188) 1H NMR (500 MHz, CDCl3) delta 7.45 (d, J=8.8 Hz, 1H), 6.99 (d, J=3.0 Hz, 1H), 6.74 (dd, J=8.8, 3.0 Hz, 1H), 4.56 (s, 2H), 3.80 (s, 3H). 13C NMR (126 MHz, CDCl3) delta 159.28, 137.90, 134.06, 116.67, 116.27, 114.85, 55.71, 33.61. HRMS (EI+) Calculated for C8H8OBr2: 277.89422; Found: 277.89402.

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-Bromo-4-methoxy-2-methylbenzene, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; The Board of Trustees of the University of Illinois; BURKE, Martin D.; CROUCH, Ian; LEHMANN, Jonathan; PALAZZOLO, Andrea; SIMONS, Claire; US2018/305381; (2018); A1;,
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Synthetic Route of 52189-63-6,Some common heterocyclic compound, 52189-63-6, name is 1-Fluoro-3,5-dimethoxybenzene, molecular formula is C8H9FO2, 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.

Example 53 3- {4- [3-Fluoro-5- (2-phenoxy-4-trifluoromethyl-phenoxy)-phenoxy]-2-methyl-phenyl}- propionic acid Step A 3-Fluoro-5-methoxy-phenol A-78 C solution of l-fluoro-3, 5-dimethoxybenzene (4. 98 g, 31.9 mmol) in dry CH2C12 (50 mL) is treated with a 1 M CH2C12 solution of boron tribromide (128 mL, 128 mmol), and the mixture is warmed to 0 C and stirred under N2. Upon completion, the mixture is poured into ice water and extracted with Et2O. The organic layer is dried (Na2S04), and the solvent is removed in vacuo to afford crude product that is absorbed on silica gel and purified by flash chromatography using a gradient of 5/1 to 1/1 to hexanes/ethyl acetate to afford 2.40 g (53%) of the title compound. Rf= 0.49 (1/1 hexanes/EtOAc).’H NMR (400 MHz, CDCl3). MS (ES-) m/z mass calculated for C7H702F 142, found 141 (M-1,100%).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 1-Fluoro-3,5-dimethoxybenzene, its application will become more common.

Reference:
Patent; ELI LILLY AND COMPANY; WO2005/37763; (2005); A1;,
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Synthetic Route of 103-50-4, 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 103-50-4 as follows.

General procedure: To a test tube charged with CuCl (2.0 mg, 0.02 mmol) andisochroman (1a; 251 muL, 2.0 mmol) in t-BuOH (20 mL) wasadded TBHP (5.0-6.0 M in decane, 10.9 muL, 0.6 mmol) and themixture was stirred and heated at 50 C for 12 h under open air.After cooling to room temperature, the reaction was quenchedwith 25% aqueous ammonia solution and water then themixture was extracted with EtOAc. The separated organic layerwas dried over Na2SO4 and products were concentrated after filtration.The residue was purified by silica gel column chromatography(EtOAc/hexane, 1:10) to give isochromanone (2a) as acolorless oil in 83% yield.

According to the analysis of related databases, 103-50-4, the application of this compound in the production field has become more and more popular.

Reference:
Article; Tanaka, Hirotaka; Oisaki, Kounosuke; Kanai, Motomu; Synlett; vol. 28; 13; (2017); p. 1576 – 1580;,
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Electric Literature of 702-24-9, 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. 702-24-9, name is 4-Methoxy-N-methylbenzylamine, This compound has unique chemical properties. The synthetic route is as follows.

A solution of 8-bromo-6-chloroimidazo[l,2-b]pyridazine-3-carbonitrile (2.82 g, 13.23 mmol), l-(4-methoxyphenyl)-N-methylmethanamine (2.00 g, 13.23 mmol) and diisopropylethylamine (4.62 mL, 26.5 mmol) in tetrahydrofuran (25 mL) was heated to 60 °C for 3 hours and then concentrated to dryness. The crude product was triturated with methanol and filtered rinsing with methanol. The solid was dried and collected as is (3.85 g, 89percent yield). NMR (400MHz, CHLOROFORM-d) delta 7.99 (s, 1H), 7.16 (d, J=8.8 Hz, 2H), 6.93 – 6.82 (m, 2H), 6.12 (s, 1H), 5.45 (br. s., 2H), 3.80 (s, 3H), 3.20 (br. s., 3H). LC retention time 1.05 min [J]. MS (E+) m/z: 328 (MH+).

The chemical industry reduces the impact on the environment during synthesis 4-Methoxy-N-methylbenzylamine. I believe this compound will play a more active role in future production and life.

Reference:
Patent; BRISTOL-MYERS SQUIBB COMPANY; WEINSTEIN, David S.; MOSLIN, Ryan M.; ZHANG, Yanlei; GARDNER, Daniel S.; SANTELLA, Joseph B.; LANGEVINE, Charles M.; STACHURA, Sylwia; (127 pag.)WO2017/87590; (2017); A1;,
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Application of 39538-68-6, A common heterocyclic compound, 39538-68-6, name is 2-Methoxy-4-methylaniline, molecular formula is C8H11NO, 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.

(Step 1)Synthesis of 2-methoxy-4-methylphenyl isothiocyanate (compound represented by formula (b)) N 1,1′-thiocarbonyldiimidazole (6.10 g), N-dimethylformamide (80 ml) solution, at room temperature, 2-methoxy-4-N methyl aniline (3.43 g), N-dimethylformamide solution (40 ml) was added and stirred for 1 hour. Then water was added at 0 , and extracted with ethyl acetate. The organic layer was washed with water, then washed with saturated brine. Then, the organic layer was dried over anhydrous magnesium sulfate, filtered, then concentrated in vacuo. The resulting crude product was purified by silica gel column chromatography, to obtain the desired product (4.53g).

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; NIPPONSODA COMPANY LIMITED; SHIMIZU, KAZUYA; SAKAMOTO, RIE; TAKAHASHI, JUN; KANAZAWA, JYUN; (37 pag.)JP2016/29022; (2016); A;,
Ether – Wikipedia,
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Synthetic Route of 1535-73-5, 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. 1535-73-5, name is 3-Trifluoromethoxyaniline belongs to ethers-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below.

3-(trifluoromethoxy)phenylamine (50 mg, 0.28 mmol) was dissolved in dry DCM (5 mL) , triethylamine (56 mg, 0.52 mmol) and triphosgene (27 mg, 0.094 mmol) were added to the reaction mixture and stirred at room temperature for three hours. In the reaction solution N-(6-(3-amino-4-fluorophenoxy)benzo[d]thiazol-2-yl)cyclopropanecarboxamide (96 mg, 0.28 mmol) was added thereto, and after reacting for 2 h, the reaction mixture was evaporated to dryness.The residue was directly purified by column chromatography (eluent: dichloromethane / methanol = 100:3). Finally, 32 mg of a white solid was obtained in a yield of 20percent.

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, 3-Trifluoromethoxyaniline, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; Second Military Medical University; Zhuang Chunlin; Miao Zhenyuan; Zhang Hao; Chen Xiaofei; Cai Zhenyu; Zhang Wannian; Xu Lijuan; (36 pag.)CN109053630; (2018); A;,
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Related Products of 204452-91-5, The chemical industry reduces the impact on the environment during synthesis 204452-91-5, name is 7-(Dimethoxymethyl)-1,2,3,4-tetrahydro-1,8-naphthyridine, I believe this compound will play a more active role in future production and life.

[0928] To a solution of phosgene (20% solution in toluene,0.186 ml, 0.353 mmol) in THF (2 ml) was added triethylamine(0.141 ml, 1.01 mmol). To the resulting white suspensionwas added a solution of 7-(dimethoxymethyl)-1,2,3,4-tetrahydro-1,8-naphthyridine (intermediate 4, 70 mg, 0.336mmol) in THF (2 ml) drop wise. The resulting yellow suspensionwas stirred at room temperature for 1 h. 4,5-dichloropyridin-2-amine (65.7 mg, 0.403 mmol) in THF (1 ml) wasadded to the mixture and stirred at room temperature for 16 h.The reaction mixture was filtered through a silica gel plug andwashed with heptanes/EtOAc 1:1 (35 ml), the filtrate wasconcentrated. The residue was dissolved in dioxane (1 ml)and treated with HCl (4 Min dioxane, 1 ml, 4.0 mmol). Themixture was stirred at room temperature for 2 h, diluted withDCM and quenched with saturated aqueous NaHC03 . Theorg. layer was collected and the water layer was extractedwith DCM. The combined org. layers were dried over anhydrousNa2S04 and concentrated under reduced pressure. Thecrude product was dissolved in acetonitrile/NMP/TFA, filteredthrough a syringe filter (0.2 f.tm) and purified by preparativereverse phase LC-MS (RP 1). The clean fractionswere combined and lyophilized to obtain the title compoundas an off white solid.

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, 7-(Dimethoxymethyl)-1,2,3,4-tetrahydro-1,8-naphthyridine, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; Novartis AG; Buschmann, Nicole; Fairhurst, Robin Alec; Furet, Pascal; Knoepfel, Thomas; Leblanc, Catherine; Liao, Lv; Mah, Robert; Nimsgern, Pierre; Ripoche, Sebastien; Xiong, Jing; Han, Bo; Wang, Can; Zhao, Xianglin; US2015/119385; (2015); A1;,
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Electric Literature of 67191-35-9, 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. 67191-35-9 name is 1-Isopropoxy-2-vinylbenzene, 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.

Under anhydrous and anaerobic conditions,Grubbs first generation catalyst 1a (1.22mmol)Add to a 100mL Schlenk bottle,Compound IIIba (2863 mg, 2.43 mmol) andPotassium tert-butoxide (477 mg, 4.25 mmol)It was added to the reaction flask, and 50 mL of n-hexane was added.After reacting for 5 hours at 60 C with stirring, the reaction was monitored by TLC.After the reaction was completed, n-hexane was removed under reduced pressure.The intermediate obtained in the previous step was dissolved in 40 mL of dichloromethane.Add cuprous chloride (300 mg, 1.42 mmol) and stir for 5 min.Compound 2a1 (296 mg, 1.82 mmol)It was added to the reaction flask, and the temperature was raised to 40 C, and the reaction was monitored by TLC.After completion of the reaction, column chromatography gave 568 mg of pale green solid powder IIba1, yield: 32.0%.

At the same time, in my other blogs, there are other synthetic methods of this type of compound, 1-Isopropoxy-2-vinylbenzene, and friends who are interested can also refer to it.

Reference:
Patent; Chengdu Kaimeisi Business Wu Information Advisory Center (Limited Partner); Chen Jianxin; (28 pag.)CN110041262; (2019); A;,
Ether – Wikipedia,
Ether | (C2H5)2O – PubChem

Application of 4342-46-5, 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. 4342-46-5, name is 4-Methoxycyclohexanamine belongs to ethers-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below.

Ethylcyclohexane (1200 mL) was added to the autoclave, stirring was started, and 220 g (2 mol) of formamide was added to the solution at a concentration of 40%. After stirring for 10 minutes, 1-amino-4-methoxycyclohexane (130 g, 1 mol) was added. ,Into the reaction kettle to pass CO, so that the pressure in the kettle reaches 0.2MPa, heated to 130 C, heat 20h, in the control of raw materials <2%, the reaction is over, cooled to 25 ~ 30 C, dilute hydrochloric acid was added dropwise to the reaction solution , Adjust the pH to 5-6, there is a solid precipitation, filter out the product, filter cake shampoo once,cis-8-Methoxy-1,3-diazaspiro[4,5]-nonane-2,4-dione, 184 g, yield 92%. The synthetic route of 4-Methoxycyclohexanamine has been constantly updated, and we look forward to future research findings. Reference:
Patent; Henan Zi Wei Xing Chemical Co., Ltd.; Wu Doucan; Mao Longfei; Li Wei; Lu Zhiguo; Wang Zhenggang; Lu Biao; Jia Shuhong; Yuan Zhiguo; (10 pag.)CN107827881; (2018); A;,
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41365-75-7, name is 1-Amino-3,3-diethoxypropane, 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. Product Details of 41365-75-7

Part A A solution of 1-amino-3,3-diethoxypropane (5.00 ML, 30.9 mmol) in 5 ML of tetrahydrofuran (THF) was treated with triethylamine (4.51 ML, 34.0 mmol) under an atmosphere of nitrogen and cooled to 0 C. The reaction mixture was then treated dropwise with a solution of di-tert-butyl dicarbonate (7.42 g, 34.0 mmol) in 25 ML of THF. The reaction mixture was stirred for 2 h at 0 C. and then allowed to come to room temperature.After 15 h, the reaction mixture was concentrated under reduced pressure, dissolved in ethyl acetate, washed with water (2*) and brine, dried over Na2SO4, filtered and concentrated under reduced pressure to yield tert-butyl (3,3-diethoxypropyl)carbamate (8.40 g) as a clear, faintly yellow oil.

The synthetic route of 41365-75-7 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; 3M Innovative Properties Company; US2004/176367; (2004); A1;,
Ether – Wikipedia,
Ether | (C2H5)2O – PubChem