Category: ethers-buliding-blocks

Related Products of 35896-58-3, These common heterocyclic compound, 35896-58-3, name is 1,2,3,4-Tetramethoxy-5-methylbenzene, 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.

A mixture of 2,3,4,5-tetramethoxytoluene (2.12 g, 10 mmol) and 1,1-dichlorodimethyl ether (1.8 mL, 20 mmol) in DCM (200 mL) was stirred at room temperature (rt), then the solution was allowed to cool to 0 oC and was added titanium tetrachloride (2.18 mL, 20 mmol). The mixture was allowed to warm to rt and stirred for 4 hours. The ice water was added slowly to quench the reaction and extracted with DCM, washed with brine and dried over Na2SO4, filtered and evaporated in vacuo. The resulting residue was purified by flash column chromatography on silica gel (EtOAc / petroleum ether = 1 / 20) to yield the target products (2 g, 83%) as colorless oil. 1H NMR (400 MHz, CDCl3) delta 10.43 (s, 1H), 4.02 (s, 3H), 3.94 (s, 3H), 3.91 (s, 3H), 3.76 (s, 3H), 2.46 (s, 3H). MS (ESI): m/z 241.1 [M+H]+.

The synthetic route of 35896-58-3 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Ding, Yuyang; Tang, Fei; Xue, Xiaoqian; Luo, Jinfeng; Hussain, Muzammal; Huang, Yanhui; Wang, Zhen; Jiang, Hao; Tu, Zhengchao; Zhang, Jiancun; Bioorganic Chemistry; vol. 89; (2019);,
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Reference of 3616-56-6, 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. 3616-56-6, name is 2,2-Diethoxy-N,N-dimethylethanamine belongs to ethers-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below.

Synthesis Example B17Synthesis of 8-bromo-12H-benzofuranyl[2,3-a]carbazole (compound 17)Under nitrogen, compound 16 (4.6 g, 1 eq) is initially charged and dissolved with acetic acid (185 ml) while heating to reflux.Then (dimethylamino)acetaldehyde diethyl acetal (95percent; 25 g, 10 eq.) is added dropwise to the reaction within 1 h and the mixture is stirred at reflux for 7 h.The mixture is cooled to room temperature and diluted with methylene chloride.In a separating funnel, the organic phase is washed with distilled water and then with saturated NaCl solution.The organic phase is dried with sodium sulfate and concentrated. LC (reverse phase, acetonitrile) gives 1.35 g of product (27.3percent yield).1H NMR (CD2Cl2; 400 MHz): delta=8.73 (s, 1H), 8.17 (s, 1H), 8.16 (d, 1H), 8.08 (d, 1H), 7.78 (d, 1H), 7.60 (d, 1H), 7.56 (m, 2H), 7.49 (dd, 1H), 7.31 (dd, 1H).

The synthetic route of 2,2-Diethoxy-N,N-dimethylethanamine has been constantly updated, and we look forward to future research findings.

Reference:
Patent; BASF SE; OSRAM OPTO SEMICONDUCTORS GMBH; KONINKLIJKE PHILIPS ELECTRONICS N.V.; US2011/266528; (2011); A1;,
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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 14869-41-1 as follows. Computed Properties of C4H7ClO3

2-(2-Chloroethoxy)acetic acid (1.0 g, 7.2 mmol) was dissolved in dichloromethane (10.0 mL)Then oxalyl chloride (1.2 mL, 14 mmol) was added and stirred at room temperature for 4 hours.Evaporate the solvent under reduced pressure.The crude product was used directly in the next reaction.

According to the analysis of related databases, 14869-41-1, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Guangdong Dongyangguang Pharmaceutical Co., Ltd.; Wang Xiaojun; Zuo Yinglin; Yu Chuan; Yang Chuanwen; Wang Jiancheng; Li Jing; Cao Shengtian; Wu Fangyuan; Zhang Yingjun; S ¡¤geerdeman; (79 pag.)CN108690016; (2018); A;,
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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. 20781-20-8, name is (2,4-Dimethoxyphenyl)methanamine, This compound has unique chemical properties. The synthetic route is as follows., category: ethers-buliding-blocks

Saturated NaHC03 (100 mL) was added to a solution of (2,4- dimethoxyphenyl)methanamine (10 mL, 66.4 mmol) in CH2CI2 (100 mL) and the mixture was stirred vigorously at 25 C for 15 min. Then thiophosgene (10 mL, 131 mmol) was added via syringe to the bottom layer. The mixture was stirred at 25 C for 1.5 h. The aqueous layer was separated and the organic layer was washed with brine (100 mL), dried over NaSC>4, filtered, and concentrated in vacuo to afford l-(isothiocyanatomethyl)-2,4-dimethoxy benzene. HNMR (400 MHz, CDCI3): delta 7.19 (d, J = 7.6 Hz, 1H), 6.47-6.50 (m, 2H), 4.61 (s, 2H), 3.84 (s, 3H), 3.82 (s, 3H).

According to the analysis of related databases, 20781-20-8, the application of this compound in the production field has become more and more popular.

Reference:
Patent; MERCK SHARP & DOHME CORP.; THE WALTER AND ELIZA HALL INSTITUTE OF MEDICAL RESEARCH; KHAN, Tanweer, A.; CUMMING, Jared, N.; OLSEN, David, B.; BODDEY, Justin, A.; COWMAN, Alan, F.; SLEEBS, Brad, E.; (86 pag.)WO2017/142825; (2017); A2;,
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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. 112970-44-2, name is 2-Bromo-3-methoxyaniline, A new synthetic method of this compound is introduced below., category: ethers-buliding-blocks

A mixture of compound 58-1 (200 mg, 989.86 umol, 1 eq.), compound 58-1 (243.76 mg, 1.19 mmol, 1.2 eq.) and EDCI (284.64 mg, 1.48 mmol, 1.5 eq.) in pyridine (3 mL) was stirred at 20 C for 12 hours. The mixture was diluted with EtOAc (30 mL), washed with 1 N hydrochloric acid solution (20 mL*3) dried with sodium sulfate, filtered and concentrated. The residue was purified by prepTLC (PE:EA = 3:1) to give compound 58-2 (150 mg,, yield: 38 %) as brown oil. LCMS: 391.1 [M+ 11

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; TREVENA, INC.; PITIS, Philip Michael; BOYD, Robert Eugene; DAUBERT, Tamara Ann Miskowski; HAWKINS, Michael John; LIU, Guodong; SPEERSCHNEIDER, Aimee Crombie; (355 pag.)WO2018/231745; (2018); A1;,
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Synthetic Route of 116557-46-1, A common heterocyclic compound, 116557-46-1, name is 3-Bromo-2-methoxyaniline, molecular formula is C7H8BrNO, 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.

Preparation 10 To a reaction vial charged with 3-bromo-2-methoxyaniline (from Step 4 of Preparation 9, 1.12 g, 5.54 mmol), l-methyl-4-(4,4,5,5-tetramethyl-l,3,2-dioxaborolan-2- yl)-lH-pyrazole (1.499 g, 7.21 mmol) in dioxane (6 mL) was added aqueous potassium phosphate (2.0 M) (5.54 ml, 11.09 mmol). The resulting mixture was deoxygenated by bubbling argon through the mixture for ~5 min. PdCl2(dppf) (0.122 g, 0.166 mmol) was then added and the mixture was heated at 110 C for 2h. The reaction was cooled, diluted with EtOAc (200 mL), washed with water, brine, dried over anhyd sodium sulfate, filtered and concentrated to afford tan oil as the crude product mixture. This material was purified by silica gel flash chromatography using hexanes/ethyl acetate mixtures as the eluant. Fractions containing the desired product were collected, combined, and concentrated under vacuum to afford 0.87 g (77%) of the desired product (Preparation 10) as an oil which solidified upon standing. HPLC (method N) = 0.89 min. LCMS MH+ 204.1.

The synthetic route of 116557-46-1 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; BRISTOL-MYERS SQUIBB COMPANY; MOSLIN, Ryan M.; WEINSTEIN, David S.; WROBLESKI, Stephen T.; ZHANG, Yanlei; TOKARSKI, John S.; MERTZMAN, Michael E.; LIU, Chunjian; WO2015/69310; (2015); 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. 102-52-3, name is 1,1,3,3-Tetramethoxypropane, A new synthetic method of this compound is introduced below., Product Details of 102-52-3

100 g of Compound 1 was added to 96 ml of water, and 5.4 ml of hydrochloric acid and 105.6 g of liquid bromine were slowly added dropwise at 0 C, and stirred at room temperature overnight.The water was spun off at 45 C, filtered, and the solid was washed several times with PE: EA and dried to give 50 g of Intermediate 3.

The synthetic route of 102-52-3 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Yaoya Science And Technology (Shanghai) Co., Ltd.; Zeng Zhaosen; Liang Yonghong; (6 pag.)CN109824586; (2019); A;,
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Adding a certain compound to certain chemical reactions, such as: 168971-68-4, name is 1-Bromo-2-fluoro-4-(trifluoromethoxy)benzene, 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 168971-68-4, Formula: C7H3BrF4O

Example 106Preparation of Compound 416CF3Step A – synthesis of compound 206BCompound 206A (2.14 g, 8.3 mmol) was combined with PdCl2(dppf) (0.20 g, 0.25 mmol), bis(pinicolato)diboron (2.52 g, 9.9 mmol), and KOAc (2.43 g, 24 mmol) in DMSO (10 mL). The mixture was put under N2 atmosphere, heated to 1000C and allowed to stir at this temperature for 4 hours, then partitioned with water and 1 : 1 EtOAc/hexane. The organic phase was dried (MgSO4) and concentrated in vacuo, and the resulting residue was purified using flash column chromatography on silica (10% EtOAc/hexane) to provide compound 206B as a white solid.

At the same time, in my other blogs, there are other synthetic methods of this type of compound, 1-Bromo-2-fluoro-4-(trifluoromethoxy)benzene, and friends who are interested can also refer to it.

Reference:
Patent; SCHERING CORPORATION; WO2008/130581; (2008); 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. 1758-46-9, name is 2-Phenoxyethylamine, A new synthetic method of this compound is introduced below., HPLC of Formula: C8H11NO

[0070] [6-CHLORO-N- (2-METHOXYBENZYL)-NAPOS;- (2-PHENOXYETHYL)- [1,] 3, 5] triazine- 2, 4-diamine (3). Procedure 1 : 1.00 eq. of 2 in [CH2C12] is cooled to ODC under nitrogen and Et3N or Hunig’s base (3.00 eq. ) is added. To the stirring solution, 1.00 eq. [OF 2-PHENOXY-ETHYLAMINE] is added dropwise. The temperature rises several degrees upon completion of addition ; warming is then allowed to continue until the reaction reaches room temperature. The reaction is allowed to stir at room temperature for 12 hours and then the mixture is partitioned between [CHUCK] and 1.0 N [HC1.] The acid layer is extracted once with [CH2C12] and then the pooled [CH2C12] layers washed several times with H20 and once with brine. The [CH2CI2] extract is dried over [NA2S04,] and the solvent removed under reduced pressure to provide crude 3, which is purified by flash chromatography using 1: 4 ethyl acetate (EtOAc)/hexanes as eluent. [0071] Procedure 2: 1.00 eq. of 2 in CH2C12 is cooled to [OOG] under nitrogen and Et3N or Hunig’s base (3.00 eq. ) is added. To the stirring solution, 1.00 eq. of 2- [PHENOXY-ETHYLAMINE] is added dropwise. The temperature rises several degrees upon completion of addition; warming is then allowed to continue until the reaction reaches room temperature. The resulting mixture is heated to [100¡ãC] for 30 minutes, cooled to room temperature, and partitioned between [H20/CH2C12.] The aqueous layer is extracted with [CH2C12] and combined organic extracts were dried over [NA2S04.] The solvent is removed under reduced pressure and the resulting residue is purified by flash chromatography [(1] : 4 EtOAc/hexanes) to yield 3.

The synthetic route of 1758-46-9 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; CELLULAR GENOMICS, INC.; WO2004/820; (2003); A2;,
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Reference of 22483-09-6, 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 22483-09-6 as follows.

A solution of phthalic anhydride (10.00 g), aminoacetaldehyde (7.81 g) and N,N-diisopropylethylamine (13.09 g) in toluene under an atmosphere of nitrogen was heated at 120 C for 16 h and then quenched with NH4C1(aq) (100 mL, 2 M). The aqueous phase was extracted with ethyl acetate (3×50 mL). The combined organic extracts were washed with water and brine, dried over anhydrous sodium sulfate, filtered. The filtrate was concentrated to get the crude residue S-I-I (15.49 g, y: 98%).

According to the analysis of related databases, 22483-09-6, the application of this compound in the production field has become more and more popular.

Reference:
Patent; NATIONAL HEALTH RESEARCH INSTITUTES; SHIH, Chuan; SHIA, Kak-Shan; WU, Chien-Huang; CHOI, Ming-Chen; SONG, Jen-Shin; WANG, Yun; (84 pag.)WO2018/132326; (2018); A1;,
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