Tag: M.W=200-300

Synthetic Route of 6358-77-6, A common heterocyclic compound, 6358-77-6, name is 5-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.

A solution of sodium nitrite (1 .78 g, 25.87 mmol) in water (5 mL) was slowly added to a cooled (-10 C) suspension of 5-bromo-2-methoxyaniline (5.0 g, 24.87 mmol) in 6N HCI aq. (13 mL) so as to keep the internal temperature below 0 C. The mixture was stirred for another 20 mm at 0 C, then a solution of stannous chloride dihydrate (14.1 g, 72.1 mmol) in conc. aq. HCI (25 mL) was added slowly. The reaction mixture was stirred an additional 1 .5 h at 0 C. The pH of the reaction mixture was carefully adjusted to -8 with sat. aq. NaHCO3. The mixture was extracted with EtOAc and the combined organic layers were dried over Na2SO4, filtered, and concentrated. The resulting residue was purified by trituration with pentane to give the title compound. MS (ESl+) m/z 217.0 (M(79Br)+H).

The synthetic route of 6358-77-6 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; NOVARTIS AG; ADAMS, Christopher; EHARA, Takeru; (134 pag.)WO2017/103888; (2017); 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. 74137-36-3, name is 1,3-Dibromo-5-methoxybenzene, A new synthetic method of this compound is introduced below., Recommanded Product: 1,3-Dibromo-5-methoxybenzene

step 2-To a solution of 57b (60 g, 0.2256 mol) and anhydrous Et2O (1 L) cooled to -78 C. and maintained under an Ar atmosphere was added dropwise over 30 min n-BuLi (100 mL, 0.2482 mol, 2.5M in hexane). The yellow solution was stirred at -78 C. for 20 min. To the reaction mixture was added dropwise dry DMF (19 mL, 248.2 mmol) over 15 min and the reaction stirred at -78 C. for 10 min before the cooling bath was removed and the reaction allowed to warm to -30 C. over 30 min. The reaction vessel was placed in an ice-water bath and warmed to -10 C. The mixture was slowly added to an ice cold saturated aqueous NH4Cl solution (400 mL). The organic layer was separated and the aqueous phase thrice extracted with Et2O. The combined extracts were washed with water, dried (MgSO4), filtered and evaporated to afford an oil which solidified on standing. The crude product was purified by SiO2 chromatography eluting with a hexane/EtOAc gradient (97:3 to 95:5) to afford 58.

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; Roche Palo Alto LLC; US2006/25462; (2006); 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. 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. name: 1-Bromo-4-methoxy-2-methylbenzene

This experiment was carried out four times. Tributyl(methoxy)stannane (400 g, 1.24 mol), 1-bromo-4-methoxy-2-methylbenzene (250 g, 1.24 mol), prop-1-en-2-ylacetate (187 g, 1.87 mol), palladium(ll) acetate (7.5 g, 33 mmol) and tri-otolylphosphine (10 g, 33 mmol) were stirred together in toluene (2 L) at 100 00 for 18 hours. After it had cooled to room temperature, the reaction mixture was treated with aqueous potassium fluoride solution (4 M, 400 mL) and stirred for 2 hours at 40 00. The resulting mixture was diluted with toluene (500 mL) and filtered through diatomaceousearth; the filter pad was thoroughly washed with ethyl acetate (2 x 1.5 L). The organic layer from the combined filtrates was dried over sodium sulfate, filtered, and concentrated in vacuo. Purification via silica gel chromatography (Gradient: 0% to 5% ethyl acetate in petroleum ether) provided the product as a yellow oil. Combined yield:602 g, 3.38 mol, 68%. LCMS m/z 179.0 [M+H]. 1H NMR (400 MHz, CDCI3) oe 7.05 (d,J=8.3 Hz, 1H), 6.70-6.77 (m, 2H), 3.79 (5, 3H), 3.65 (5, 2H), 2.22 (5, 3H), 2.14 (5, 3H).

The synthetic route of 27060-75-9 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; PFIZER INC.; GRAY, David Lawrence Firman; DAVOREN, Jennifer Elizabeth; DOUNAY, Amy Beth; EFREMOV, Ivan Viktorovich; MENTE, Scot Richard; SUBRAMANYAM, Chakrapani; WO2015/166370; (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. 101-55-3, name is 1-Bromo-4-phenoxybenzene, A new synthetic method of this compound is introduced below., Application In Synthesis of 1-Bromo-4-phenoxybenzene

4-bromodiphenyl ether(6.2g, 25.0mmol) Isopropanol pinacol borate (10.3 mL, 50 mmol)Soluble in dry tetrahydrofuran,Cooled to -78C under nitrogen protection.n-Butyllithium (2.5M, 18 mL, 45 mmol) was added dropwise,After completion of the addition, the mixture was stirred for 6 hours and slowly warmed to -40C for 12 hours.The reaction was added to saturated ammonium chloride solution and extracted three times with ethyl acetate.The organic phases were combined and dried over anhydrous sodium sulfate.It was evaporated to dryness by rotary evaporation and purified by column to give 5.4 g of the target compound in a yield of 72%.

The synthetic route of 101-55-3 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Chinese Academy Of Sciences Shanghai Pharmaceutical Institute; Zhao Yujun; Chen Deheng; Yan Ziqin; Guo Dexiang; (85 pag.)CN107759602; (2018); A;,
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Synthetic Route of 57478-19-0, These common heterocyclic compound, 57478-19-0, name is 4-(4-(Trifluoromethyl)phenoxy)aniline, 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: To a solution of benzoic acid derivatives (5 or 9 or 15 or 19, 1.0 equiv.) and HATU (1.1 equiv.) in DMF at room temperature, substituted amine (1.05 equiv.) and DIPEA (1.2 equiv.) were added sequentially. The reaction mixture was stirred at room temperature for 1-2h. The resulting mixture was diluted with 5% HCl, and extracted with EtOAc. The combined organic layers were washed with saturated aqueous NaHCO3 and brine, dried over anhydrous Na2SO4, concentrated, and recrystallized from MeOH to afford the crude product.

The synthetic route of 57478-19-0 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Xie, Fangzhou; Liang, Yaoyao; Xia, Yu; Luo, Shuhua; Jiang, Faqin; Fu, Lei; Bioorganic Chemistry; vol. 92; (2019);,
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Adding a certain compound to certain chemical reactions, such as: 1663-61-2, name is (Triethoxymethyl)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 1663-61-2, Safety of (Triethoxymethyl)benzene

General procedure: The starting hydrazide 4, 8e-i (10 mmol) was added to a mixture of the appropriate triethyl orthoester (10 mol) and 0.1 g p-TsOH in 20 mL of xylene and kept under reflux for 3 h (TLC). After cooling, the mixture was washed with water (30 mL), dried over MgSO4 and then concentrated under reduced pressure. The oily residue was subjected to column chromatography (silica gel, eluent: hexane/AcOEt, 1:2 v/v) or crystallised from benzene/hexane mixture.

If you are interested in these compounds, you can also browse my other articles.Thank you for taking the time to read this article. I hope you enjoyed it.

Reference:
Article; Kudelko, Agnieszka; Zielin?ski, Wojciech; Ejsmont, Krzysztof; Tetrahedron; vol. 67; 40; (2011); p. 7838 – 7845;,
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Adding a certain compound to certain chemical reactions, such as: 29578-39-0, name is 1-Bromo-3-fluoro-5-methoxybenzene, 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 29578-39-0, HPLC of Formula: C7H6BrFO

To a solution of Compound 187 (0.700 g, 3.41 mmol) in 1,4-dioxane (5 ml) were added Compound 188 (0.861 g, 4.10 mmol) and PdCl2(dtbpf) (0.223 g, 0.341 mmol), and then 2 mol/L aqueous solution of potassium carbonate (2.561 ml, 5.12 mmol), and the reaction mixture was stirred at 70C. After completion of the reaction, water was added to the reaction mixture, and the resulting mixture was extracted with chloroform, which was then concentrated under reduced pressure. The obtained residue was purified by silica gel column chromatography to obtain Compound 189 (0.667 g, 93.8%). Compound 189; Method B LC/MS retention time = 1.99 min. MS (ESI) m/z = 209.35(M+H)+.

At the same time, in my other blogs, there are other synthetic methods of this type of compound, 1-Bromo-3-fluoro-5-methoxybenzene, and friends who are interested can also refer to it.

Reference:
Patent; Shionogi & Co., Ltd.; TAMURA, Yuusuke; HINATA, Yu; KOJIMA, Eiichi; OZASA, Hiroki; (241 pag.)EP3187498; (2017); A1;,
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Application of 25245-34-5,Some common heterocyclic compound, 25245-34-5, name is 2-Bromo-1,4-dimethoxybenzene, molecular formula is C8H9BrO2, 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.

2-Bromo-1,4-dimethoxybenzene 39a (250 mg, 1.15 mmol), 2-formylphenylboronic acid 34 (207 mg, 1.38 mmol), tetrakis(triphenylphosphine)palladium(0) (133 mg, 0.29 mmol) and CsF (437 mg, 2.88 mmol) were added to a microwave vial in dimethoxyethane (2 mL) as solvent and the solution was degassed for 2 min. The reaction mixture was transferred to a microwave reactor at 150 C and 150 W power with vigorous stirring for 30 min. On completion, the reaction mass was filtered off, adsorbed on silica and subjected to column chromatography (5% EtOAc/Hexane) to yield the product 40a as white low melting solid (246 mg, 1.02 mmol, 88%). 1H NMR (500 MHz, CDCl3) d 9.79 (1H, s, CHO), 8.01-7.97 (1H, m, ArH), 7.64 (1H, td, J = 7.5, 1.2 Hz, ArH), 7.48 (1H, t, J = 7.6 Hz, ArH), 7.38-7.34 (1H, m, ArH), 6.94 (1H, dd, J = 8.9, 3.0 Hz, ArH), 6.90 (1H, d, J = 8.9 Hz, ArH), 6.87 (1H, d, J = 3.0 Hz, ArH), 3.81 (3H, s, OMe), 3.67 (3H, s, OMe); 13C NMR (126 MHz, CDCl3) d 192.5, 153.8, 150.7, 141.6, 134.0, 133.7, 131.0, 127.8, 127.7, 126.6, 117.3, 114.4, 111.8, 55.9, 55.8.

The synthetic route of 25245-34-5 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Pradeep, Priyamvada; Ngwira, Kennedy J.; Reynolds, Chevonne; Rousseau, Amanda L.; Lemmerer, Andreas; Fernandes, Manuel A.; Johnson, Myron M.; de Koning, Charles B.; Tetrahedron; vol. 72; 51; (2016); p. 8417 – 8427;,
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Related Products of 6358-77-6, These common heterocyclic compound, 6358-77-6, name is 5-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.

A solution of sodium bicarbonate (3.74 g, 44.5 mmol) in water (75 mL) was added to commercially available 5-bromo-2-methoxy-phenylamine (3 g, 14.8 mmol) in chloroform (75 mL). Thiophosgene (1.42 mL, 18.6 mmol) was then added. The biphasic solution was stirred at room temperature for 1 h. The phases were separated and the aqueous phase was extracted with CH2Cl2. The organic phase was dried (Na2SO4), filtered, and concentrated, yielding the crude title compound as an off-white solid.

The synthetic route of 6358-77-6 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; WANG, Aihua; Zhang, Yan; Leonard, Kristi Anne; Hawkins, Michael; Tounge, Brett Andrew; Maharoof, Umar S.M.; Barbay, Joseph Kent; US2012/129811; (2012); 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 1462-37-9 as follows. Quality Control of ((2-Bromoethoxy)methyl)benzene

Under Ar atmosphere, n-BuLi (1.58M in n-hexane, 0.64mL, 1.00mmol) was added to a solution of 32 (300mg, 0.773mmol) in ether (10mL) at 0¡ãC, and stirred for 1h at room temperature. Then benzyl 2-bromoethyl ether (249mg, 1.16mmol) was added to the mixture and stirred for 18h at room temperature. Then the reaction was quenched with water, and the reaction mixture was diluted with AcOEt. The organic layer was washed with water and brine, dried with Na2SO4 and concentrated. Purification by silica gel column chromatography (eluent; hexane/ethyl acetate, 20:1) gave 265mg (66percent) of 33 as colorless oil. 1H NMR (CDCl3, 400MHz) delta 7.33?7.25 (m, 5H), 4.37 (s, 2H), 3.3?1.3 (br m, 10H), 3.23 (t, J=7.1Hz, 2H), 3.23 (s, 2H), 3.08 (s, 2H), 1.93 (t, J=7.1Hz, 2H), 1.42 (q, J=7.5Hz, 4H), 0.89 (t, J=8.1Hz, 9H), 0.78 (t, J=7.5Hz, 6H), 0.51 (q, J=7.7Hz, 6H).

According to the analysis of related databases, 1462-37-9, the application of this compound in the production field has become more and more popular.

Reference:
Article; Fujii, Shinya; Kano, Atsushi; Songkram, Chalermkiat; Masuno, Hiroyuki; Taoda, Yoshiyuki; Kawachi, Emiko; Hirano, Tomoya; Tanatani, Aya; Kagechika, Hiroyuki; Bioorganic and Medicinal Chemistry; vol. 22; 4; (2014); p. 1227 – 1235;,
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