Category: ethers-buliding-blocks

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. 588-63-6, name is (3-Bromopropoxy)benzene, This compound has unique chemical properties. The synthetic route is as follows., Computed Properties of C9H11BrO

To a flame-dried Schlenk tube containing CpFe(CO)2Cl (6) (10.3 mg, 0.05 mmol),3-bromopropyl phenyl ether (1j) (223 mg, 1.04 mmol), THF (0.25 mL), n-BuMgCl (2a)(2M in THF, 0.75 mL, 1.5 mmol), and 1,3-butadiene (90 mL as gas, 4.0 mmol) wereadded successively at ?78 C followed by stirring at 0 °C for 2 h and rt for 22 h. Thereaction was quenched by the addition of sat NH4Cl aq., extracted with Et2O (10 mL x3), concentrated, and purified by PTLC (eluent: hexane/Et2O = 99/1) to obtain heptylphenyl etherS2 (3ja) as yellow oil (79.5 mg, 40percent).

According to the analysis of related databases, 588-63-6, the application of this compound in the production field has become more and more popular.

Reference:
Article; Iwasaki, Takanori; Shimizu, Ryohei; Imanishi, Reiko; Kuniyasu, Hitoshi; Kambe, Nobuaki; Chemistry Letters; vol. 47; 6; (2018); p. 763 – 766;,
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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. category: ethers-buliding-blocks

In an open ChemGlass vial with pressure -release top, a stirred mixture of 3- bromobenzaldehyde diethylacetal (Aldrich, St. Louis, MO) (65 mg, 0.25 mmol), palladium(II) acetate (5.5 mg, 0.025 mmol), 2-dicyclohexylphosphino-2′,6′- diisopropoxybiphenyl (23 mg, 0.05 mmol), K2C03 (138 mg, 1.0 mmol) and trans-2- (trifluoromethyl)cyclopropylboronic acid MIDA ester (99 mg, 0.38 mmol) in toluene (2.5 mL) and H20 (0.5 mL) was de-gassed with N2 for 15 minutes, then the reaction mixture placed under nitrogen, sealed and heated to 100 C and stirred overnight. After allowing to cool, the reaction mixture was diluted with H20 (15 mL) and EtO Ac (20 mL), filtered through Celite and the filter cake washed with EtO Ac (2 x 20 mL). The filtrate was partitioned and the aqueous layer extracted with EtOAc (2 x 15 mL). The combined organic extracts were dried (Na2S04), filtered and concentrated under vacuum to leave a crude residue. The residue was purified by preparative thin-layer chromatography (3 prep TLC plates used) using EtOAc / hexane (1:4) as eluent to give the product (58.6 mg, 69% – yield adjusted for purity) as an oil [note: desired product contaminated with another compound after prep TLC – approximately 85% pure by 1H NMR and LC/MS].[00221] 1H NMR (CDC13, 300MHz): delta 7.34-7.24 (m, 3H), 7.08 (dt, / = 7.1, 1.7 Hz, 1H), 5.46 (s, 1H), 3.67-3.48 (m, 4H), 2.40-2.34 (m, 1H), 1.88-1.75 (m, 1H), 1.40-1.31 (m, 1H), 1.24 (t, 7 = 7.1 Hz, 6H), 1.20-1.14 (m, 1H). 19F NMR (CDC13, 282 MHz): -66.8 (d, / = 6.8 Hz), m/z = no mass-ion by LC/MS or HRMS.

The synthetic route of 3-Bromobenzaldehyde Diethyl Acetal has been constantly updated, and we look forward to future research findings.

Reference:
Patent; RIGEL PHARMACEUTICALS, INC.; DUNCTON, Matthew; SINGH, Rajinder; WO2012/75316; (2012); A2;,
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Synthetic Route of 1462-37-9, 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. 1462-37-9, name is ((2-Bromoethoxy)methyl)benzene, This compound has unique chemical properties. The synthetic route is as follows.

Mg turnings (1.50 g, 61.70 mmol) stirred in THF (80 ml) under Ar was added ((2- bromoethoxy)methyl)benzene (13.10 g, 61.21 mmol) dropwise for 2 h, then kept to stirring for another 3 h. To the mixture was added phosphorus(V) oxychloride (1.90 ml. 20.40 mmol) at -78°C. After stirred at -78°C for 4 h, the mixture was diluted with 0.1 M NaHCQ3 solution (80 ml), NaCl (sat. 100 ml) and EtOAc (50 ml), separated, and the aqueous solution was extracted with EtOAc ( 2 x 50 ml). The organic layers were combined, dried over MgSOj. filtered, concentrated and purified on Si02 column eluted with EtOAc (1 :10 -1:6) to afford the title compound, 6.11 g (66.2percent yield). ESI MS m//+ 475.2 (M + Na).

The chemical industry reduces the impact on the environment during synthesis ((2-Bromoethoxy)methyl)benzene. I believe this compound will play a more active role in future production and life.

Reference:
Patent; HANGZHOU DAC BIOTECH CO., LTD; ZHAO, Robert Yongxin; WO2015/28850; (2015); A1;,
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Electric Literature of 5414-19-7, 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. 5414-19-7 name is 1-Bromo-2-(2-bromoethoxy)ethane, 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.

A suspension of phthalimide potassium salt (4.6 g, 19.9 mmol), 2,2 bromoethoxy ether (5.54 g, 3.00 mL, 29.9 mmol) and NaHC03 (1 .64 g, 19.9 mmol) in DMF (50 mL) was stirred for 6 h. The reaction mixture was diluted with ethyl acetate (150 mL) and washed with water (2 x 150 mL) and brine (150 mL). The organic layer was dried over Na2S04, concentrated in vacuo and purified by silica gel chromatography eluting with 1 :5 ethyl acetate/hexane to give an off white solid (Yield: 4.08 g, 69%) (0294) 1 H NMR (400 MHz, CDCI3): : delta 7.78 – 7.84 (m, 2H), 7.65 – 7.70 (m, 2H), 3.87 (t, J = 7.2 Hz, 2H), 3.71 – 3.77 (m, 4H), 3.63 (t, J = 7.5 Hz, 2H); 13C NMR (101 MHz, CDCL3): delta 168.3, 156.8, 135.7, 134.1 , 132.3, 129.6, 128.6, 128.5, 123.4, 81 .5, 77.1 , 67.7, 67.3, 49.8, 37.5, 28.4.

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

Reference:
Patent; THE UNIVERSITY OF SYDNEY; CODD, Rachel; KATSIFIS, Andrew; LIFA, Tulip; TIEU, William; RICHARDSON-SANCHEZ, Tomas; (90 pag.)WO2017/96430; (2017); A1;,
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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;,
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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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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;,
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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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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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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;,
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