Category: ethers-buliding-blocks

Reference of 59557-91-4, These common heterocyclic compound, 59557-91-4, name is 4-Bromo-2-methoxyaniline, 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.

At 5 C., a solution of bromine (9.8 mL, 192.5 mmol, 1.1 eq) in dichloromethane (120 mL) was added slowly to a dichloromethane solution (240 mL) of 4-bromo-2-methoxyaniline (35.35 g, 175 mmol) under vigorous stirring. The reaction mixture was kept at this temperature for 2 h. After the completion monitored by TLC, the reaction mixture was poured into ice water and extracted with ethyl acetate (3*200 mL). The organic layer was combined, washed with brine (3*50 mL) and dried over sodium sulfate. Then the reaction mixture was purified by flash column chromatography (ethyl acetate/hexanes (v/v)=5/95). The product (40.3 g, yield=82%) was obtained as a red liquid. 1H NMR (600 MHz, CDCl3) delta 7.20 (d, J=1.9 Hz, 1H), 6.84 (d, J=1.8 Hz, 1H), 4.21 (s, 2H), 3.86 (s, 3H). LRMS m/z 280.0 [M+H]+.

The synthetic route of 59557-91-4 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; The Regents of the University of Michigan; Cierpicki, Tomasz; Grembecka, Jolanta; Huang, Huang; Zari, Sergi; Cho, Hyo Je; Potopnyk, Mykhaylo; Dudkin, Sergeii; Chen, Wenbing; Adam, Yassir; Howard, Christina; Kim, EunGi; US2019/183865; (2019); 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. 22483-09-6, name is 2,2-Dimethoxyethanamine belongs to ethers-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below. Formula: C4H11NO2

(a) Ethyl N-(2,2-dimethoxyethyl)-carbamate 214 g (2 mol) of ethyl chloroformate are added dropwise to 214 g (2 mol) of aminoacetaldehyde dimethyl acetal in 1 l of toluene and 90 g of NaOH in 500 ml of water at 10 C. The mixture is stirred at room temperature for a further 2 hours and the aqueous phase is separated off, saturated with sodium chloride and extracted with toluene. The toluene solutions are dried over magnesium sulphate and concentrated and the residue is distilled. Yield: 338 g (95.4% of theory) Boiling point: 60 C./0.03 mbar

The synthetic route of 22483-09-6 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Bayer Aktiengesellschaft; US4990517; (1991); A;,
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Synthetic Route of 175278-09-8,Some common heterocyclic compound, 175278-09-8, name is 4-Bromo-2-(trifluoromethoxy)aniline, molecular formula is C7H5BrF3NO, 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.

General procedure: Triphosgene (0.14 g, 0.48 mmol) was dissolved in anhydrous CH2Cl2 (15 mL) and the mixture was stirred on the ice-bath for 15 min. 3-Bromo-5-(trifluoromethyl)aniline (0.3 g, 1.2 mmol) in anhydrous CH2Cl2 (10 mL) was added dropwise to the above mixture and stirring continued for 20 min. Et3N (0.2 mL, 1.44 mmol) diluted with CH2Cl2 (5 mL) was then added into the mixture. Stirring was continued for 20 min and a solution of Et3N (0.2 mL, 1.44 mmol), 4-pyridin-3-ylaniline (5) (0.2 g, 1.2 mmol) in anhydrous CH2Cl2 (20 mL) was added. After completion of the action, the reaction was quenched with dilute Na2CO3. The organic layer was washed with water and brine, and dried over Na2SO4. After filtration and concentration in vacuo, the residues was purified by silica gel flash chromatography (PE/AcOEt = 6:1) yielding (L1). yield 73%

The synthetic route of 175278-09-8 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Su, Ping; Wang, Jinfeng; Shi, Yaling; Pan, Xiaoyan; Shao, Ruili; Zhang, Jie; Bioorganic and Medicinal Chemistry; vol. 23; 13; (2015); p. 3228 – 3236;,
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Related Products of 112970-44-2, 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 112970-44-2 as follows.

Step 2. Synthesis of N-(2-bromo-3-methoxyphenyl)-2,2,2-trifluoroacetamide (C24) Trifluoroacetic anhydride (3.0 mL, 22 mmol) was added to a solution of 2-bromo-3-methoxyaniline (C23) (2.57 g, 10.77 mmol) and triethylamine (4.51 mL, 32.3 mmol) in dichloromethane (30 mL) at -78 C. The reaction was allowed to warm to room temperature and stirring was continued for 18 hours, whereupon the mixture was poured into water (40 mL) and extracted with dichloromethane (2*20 mL). The combined organic layers were dried over sodium sulfate and concentrated in vacuo. Purification via silica gel chromatography (Gradient: 0% to 30% methyl tert-butyl ether in hexanes) afforded the title compound as a colorless solid. Yield: 2.97 g, 9.96 mmol, 92%. GCMS m/z 297, 299 (M+). 1H NMR (400 MHz, CDCl3) delta 3.94 (s, 3H), 6.81 (dd, J=8.4, 1.2 Hz, 1H), 7.35 (dd, J=8.4, 8.3 Hz, 1H), 7.97 (dd, J=8.3, 1.3 Hz, 1H), 8.59 (br s, 1H).

According to the analysis of related databases, 112970-44-2, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Pettersson, Martin Youngjin; Johnson, Douglas Scott; Subramanyam, Chakrapani; O’Donnell, Christopher John; Ende, Christopher William Am; Fish, Benjamin Adam; Green, Michael Eric; Mullins, Patrick Bradley; Stiff, Cory Michael; Tran, Tuan Phong; Navaratnam, Thayalan; US2012/252758; (2012); 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. 1663-61-2, name is (Triethoxymethyl)benzene, A new synthetic method of this compound is introduced below., Recommanded Product: (Triethoxymethyl)benzene

1,1,1-Trimethoxyethane (35 mg, 0.291 mmol) and 3 mgcamphorsulfonic acid (0.012 mmol) were added to asolution of 113 mg heptoside 1 (0.242 mmol) in 1 cm3dry CH2Cl2 and stirred for 1 h at rt when TLC showed fullconversion of 1 into intermediate 11 (Rf = 0.33, hexane/EtOAc = 2/1).

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:
Article; Walter, Martin; Kohout, Claudia; Blaukopf, Markus; Kosma, Paul; Monatshefte fur Chemie; vol. 148; 1; (2017); p. 111 – 119;,
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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. 7025-06-1, name is 1-Bromo-2-phenoxybenzene, A new synthetic method of this compound is introduced below., Formula: C12H9BrO

The THF solution (50 mL) of the compound 3 (g [ 7.5 ], 40mmol) was dropped at the roomtemperature at metal magnesium (1 g, 40mmol), 1,2dibromoethane (0.2 mL), and themixture of THF (50 mL), and was stirred into them for 3 hours. The THF solution (20 mL) ofthe phosphorus trichloride (2.6 mL, 30mmol) was dropped here at 78 degree C, and it stirredat the room temperature for 1 hour. It removed under decompression of a solvent and anexcessive phosphorus trichloride, THF (50 mL) was newly added, and the solution of thecompound 4 was obtained. The solution of the compound 2 of the preceding paragraph wasdropped here at 78 degree C, and it stirred at the room temperature for 2 hours to make the solution of the compound 5.

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; JAPAN POLYETHYLENE CORPORATION; JAPAN POLYPROPYLENE CORPORATION; XIN, SHIXUAN; SHIMIZU, FUMIHIKO; SATO, NAOMASA; TANNA, AKIO; (45 pag.)JP5812764; (2015); B2;,
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Synthetic Route of 592-55-2, These common heterocyclic compound, 592-55-2, name is 1-Bromo-2-ethoxyethane, 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.

Example 2: 4- {3-Hydroxy-3- [4- (2-ethoxyethoxy)-5, 5, 8, 8- tetramethyl-5,6, 7, 8-tetrahydronaphth-2-yl] prop-1-ynyl}- benzoic acid; a. 5,5, 8, 8-Tetramethyl-4- (2-ethoxyethoxy)- 5,6, 7,8-tetrahydronaphthalene-2-carbaldehyde 36 g (156 mmol) of 4-hydroxy-5,5, 8,8-tetra- methyl-5,6, 7, 8-tetrahydronaphthalene-2-carbaldehyde are dissolved in 400 mL of anhydrous DMF. 6.5 g (163 mmol) of 60% sodium hydride are added portionwise and the reaction medium is stirred for 1 hour. 25 g (163 mmol) of 2-ethoxyethyl bromide are added portionwise and the medium is stirred at room temperature for 2 hours and then hydrolysed and extracted with ethyl ether. The organic phase is washed with 1N sodium hydroxide solution, and then three times with water. The residue obtained is purified by chromatography (eluent: heptane). A yellow oil is obtained (m = 40.7 g; yield = 86%).

The synthetic route of 592-55-2 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; GALDERMA RESEARCH & DEVELOPMENT, S.N.C.; WO2005/56510; (2005); A2;,
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Adding a certain compound to certain chemical reactions, such as: 2062-98-8, name is Perfluoro(2-methyl-3-oxahexanoyl) fluoride, 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 2062-98-8, COA of Formula: C6F12O2

While the solution containing compound (c1-1) was stirred at 0C, 1.7 g of triethylamine was added. Then, 4.4g of 2-(heptafluoropropoxy)-2,3,3,3-tetrafluoropropionic acid fluoride (compound d1-1) was dropwise added. After completionof dropwise addition, the solution was stirred at room temperature for 1 hour to obtain a solution containingcompound (m1-1). The solution containing compound (m1-1) was poured into ice water, followed by extraction three times withethyl acetate. Then, the resulting organic layer was dried over magnesium sulfate to remove the solvent, and the residuewas purified by silica gel column chromatography (eluent: ethyl acetate/hexane=1/2 (volume ratio)) to obtain 2.0 g ofcompound (m1-1). Compound (m1-1) was identified by 1H-NMR and 19F-NMR. NMR spectra of compound (m1-1): 1H-NMR (300.4MHz, solvent:CDCl3, standard:TMS) delta (ppm): 1.85(s, 6H), 4.27(t, J=4.8, 2H), 4.52(t, J=4.8, 2H),5.87(dd, J=10.5, 10.8, 1 H), 6.16(dd, J=10.5, 17.1, 1H), 6.45(dd, J=17.1, 17.4, 1H), 6.92(d, J=9.0, 2H), 7.90(d,J=9.0, 2H). 19F-NMR(282.7MHz, solvent:CDCl3, standard:CFCl3)delta5(ppm):-132.0(m, 1F), – 129.6(m, 2F), -85.4(m, 1F), -81.2(m, 6F), -79.5(m, 1F).

At the same time, in my other blogs, there are other synthetic methods of this type of compound, Perfluoro(2-methyl-3-oxahexanoyl) fluoride, and friends who are interested can also refer to it.

Reference:
Patent; Asahi Glass Company, Limited; ITO, Masahiro; TSURUOKA, Kaori; EP2792665; (2014); A1;,
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Reference of 929-75-9, A common heterocyclic compound, 929-75-9, name is 1,11-Diamino-3,6,9-trioxaundecane, molecular formula is C8H20N2O3, 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.

General procedure: All macrocyclic compounds were obtained as previously described. 20,21 The corresponding diester (1-3) (10 mmol) and diamine (4-8) (10 mmol) were dissolved in MeOH (100 ml). The reaction mixture was stirred for 7 d at rt. After completion of the reaction (monitored by TLC), the solvent was evaporated and the residue was puriofied by chromatography on a silica gel column using 0-5% solutions of MeOH/CH2Cl2. Analytical and spectroscopic data are collected in the Supplementary Materials.

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:
Article; Pikus, Grzegorz; Pa?niczek, Ewa; Jurczak, Janusz; Arkivoc; vol. 2017; 2; (2017); p. 534 – 545;,
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Electric Literature of 20781-20-8, 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. 20781-20-8, name is (2,4-Dimethoxyphenyl)methanamine belongs to ethers-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below.

To a solution of 2,4-dimethoxybenzylamine (6.6 mL, 43.5 mmol) in DCM (85 mL) was added saturated aqueous sodium bicarbonate solution (85 mL) and the mixture was stirred vigorously at RT for 15 min. Stirring was stopped then thiophosgene (6.6 mL, 87 mmol) was added via syringe to the bottom layer. The mixture was stirred at RT for 90 min then the aqueous layer was separated and the organic layer was washed with brine, dried over Na2SC>4 and concentrated in vacuo twice from DCM to give 9.1 g of l-(isothiocyanatomethyl)-2,4-dimethoxybenzene as yellow oil.

The synthetic route of (2,4-Dimethoxyphenyl)methanamine has been constantly updated, and we look forward to future research findings.

Reference:
Patent; MERCK SHARP & DOHME CORP.; MCKITTRICK, Brian; CALDWELL, John, P.; MCCAULEY, John, A.; VACCARO, Henry; CHAN, Tin-Yau; KIM, Hyunjin; SMITH, Elizabeth; HONG, Liwu; KHAN, Tanweer; YING, Shihong; WANG, Hongwu; (66 pag.)WO2018/118827; (2018); A1;,
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