Ethers-buliding-blocks

Application of 17715-69-4,Some common heterocyclic compound, 17715-69-4, name is 1-Bromo-2,4-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.

General procedure: A suspension of Pd2(dba)3 (6.9mg, 0.0075mmol), tBu3PHBF4 (8.7mg, 0.03mmol), KOH (42mg, 0.75mmol), aryl bromide 4 (0.36mmol) and tetralone 3 (0.3mmol) in a mixture of dioxane/water (4:1, v/v, 3mL) was degassed and heated under Ar and microwave irradiation (80W of initial power, 100°C, 40min, infrared probe). Then, the mixture was allowed to cool to rt, diluted in AcOEt, washed with saturated NH4Cl solution, dried over anhydrous Na2SO4, filtered and concentrated under reduced pressure. The crude material was purified by silica gel chromatography. Dioxane quality is extremely important for the success of the reaction. Characterization of alpha-aryl-alpha-tetralones is given in Ref.[26].

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 1-Bromo-2,4-dimethoxybenzene, its application will become more common.

Reference:
Article; Fernandes, Talita de A.; Costa, Paulo R. R.; Manvar, Dinesh; Basu, Amartya; Kaushik-Basu, Neerja; Domingos, Jorge L. O.; Nichols, Daniel Brian; European Journal of Medicinal Chemistry; vol. 112; (2016); p. 33 – 38;,
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Application of 2398-37-0, A common heterocyclic compound, 2398-37-0, name is 1-Bromo-3-methoxybenzene, molecular formula is C7H7BrO, 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 reaction tube charged with NBS (1.5 equiv, 0.3 mmol), catalyst (10 mol%, 0.02 mmol) and CH3CN (1.0 mL),was added para-chloroanisole 1a (0.2 mmol). After being stirred at room temperature for 12 h in dark, the reaction was quenched by saturated aq. solution of Na2S2O3 (2 mL). The resulting mixture was extracted by ethyl acetate (3 5 mL). The combined organic extracts were washed by brine (10 mL), dried over Na2SO4 and filtered through a pad of Celite. The filtrate was concentrated under reduced pressure and the residuewas purified by flash chromatography on a silica gel column with petroleum ether/dichloromethane (5:1) as the eluent to give 4.3.1. 2-Bromo-4-chloroanisole (2a)

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; Pramanick, Pranab Kumar; Hou, Zhen-Lin; Yao, Bo; Tetrahedron; vol. 73; 50; (2017); p. 7105 – 7114;,
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Related Products of 169247-46-5,Some common heterocyclic compound, 169247-46-5, name is 1-(Benzyloxy)-4-bromo-2-(trifluoromethyl)benzene, molecular formula is C14H10BrF3O, 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.

Then, 5.10 g of 4-bromo-2-trifluoromethyl-1-benzyloxybenzene, 2.34 g of p-ethoxyphenol, 2.13 g of potassium carbonate, 100 mg of copper and 200 mg of cuprous chloride were charged into a reaction vessel, and stirred at 130° C. to 140° C. for 5 hours. The reaction solution was cooled to room temperature, poured into ice-water and then acidified by adding 10percent hydrochloric acid. The solution was extracted twice with 100 ml of diethyl ether. Then, the ether layers were combined, washed with water, dried over anhydrous magnesium sulfate and concentrated to give a crude product. This crude product was subjected to silica gel chromatography to give 2.50 g of 2-trifluoromethyl-4-(4-ethoxyphenoxy)-1-benzyloxybenzene (yield, 41percent).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 1-(Benzyloxy)-4-bromo-2-(trifluoromethyl)benzene, its application will become more common.

Reference:
Patent; Sumitomo Chemical Company, Limited; US5530015; (1996); A;,
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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 121588-79-2 as follows. Recommanded Product: 121588-79-2

General procedure: To a suspension of 9 (26.6 g, 76.3 mmol) in N,N-dimethylformamide (380 mL) was added 1-amino-2-methyl-propan-2-ol (8.16 g, 91.5 mmol) and triethylamine (31.9 mL, 228 mmol) at 0 C. The reaction mixture was stirred at room temperature for 5.5 h. Then the reaction mixture was diluted with cold water (1000 mL) and the mixture was stirred at room temperature for 1 h. The resulting precipitate was collected and washed with water. The precipitate was triturated with a mixture of diethyl ether and diisopropyl ether (1:1, 60 mL) to give the title compound (27.7 g, 83%) as a tan colored powder.

According to the analysis of related databases, 121588-79-2, the application of this compound in the production field has become more and more popular.

Reference:
Article; Koizumi; Tanaka, Yoshihito; Matsumura, Takehiko; Kadoh, Yoichi; Miyoshi, Haruko; Hongu, Mitsuya; Takedomi, Kei; Kotera, Jun; Sasaki, Takashi; Taniguchi, Hiroyuki; Watanabe, Yumi; Takakuwa; Kojima, Koki; Baba, Nobuyuki; Nakamura, Itsuko; Kawanishi, Eiji; Bioorganic and Medicinal Chemistry; vol. 27; 15; (2019); p. 3440 – 3450;,
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Electric Literature of 2752-17-2, 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 2752-17-2 as follows.

Compounds 1 and 2 were prepared by the following procedure: 2-(4-chloro-3-nitrophenyl)-2-oxoethyl 2-aminobenzoate or 2-(4-amino-3-nitrophenyl)-2-oxoethyl 2-aminobenzoate (44.8 mmol) was suspended in polyphosphoric acid (167.3 g). The reaction mixture was heated to 100 C and stirred for 90 min. The mixture was then poured into H2O/crushed ice (700 ml). The precipitated product was filtered, washed with H2O, dried and recrystallized from 2-methoxyethanol. Compounds 3-17 were prepared by the following general procedure: quinolinone 1 (200 mg, 0.63 mmol) was added to a solution of amine (6.3 mmol) and N-methylpyrrolidone (1.0 ml) and the mixture was stirred at 110 C for 2 h. After cooling to room temperature, H2O (20 ml) was added and the pH adjusted to 7 with dilute HCl (1:3). The precipitated solid was collected by suction, washed thoroughly with H2O and dried at 80 C. The crude product was recrystallized from 2-methoxyethanol.

According to the analysis of related databases, 2752-17-2, the application of this compound in the production field has become more and more popular.

Reference:
Article; Motyka, Kamil; Hlava?, Jan; Soural, Miroslav; Hradil, Pavel; Krej?i, Petr; Kvapil, Lubomir; Weiss, Milo?; Tetrahedron Letters; vol. 52; 6; (2011); p. 715 – 717;,
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Application of 93919-56-3,Some common heterocyclic compound, 93919-56-3, name is (4-(Trifluoromethoxy)phenyl)methanamine, molecular formula is C8H8F3NO, 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.

[000214] To a stirred solution of 6 (40 mg, 0.14 mmol) in DMF (3 mL) under argon atmosphere was added CDI (71.7 mg, 0.17 mmol) at 0 C; warmed to RT and stirred for 2 h. To this were added (4-(trifluoromethoxy) phenyl) methanamine 172 (33.8 mg, 0.17 mmol), and diisopropyl ethyl amine (0.05 mL, 0.29 mmol) and stirred for 16 h. The reaction was monitored by TLC; after completion of the reaction, the reaction mass was diluted with water (15 mL) and stirred for 1 h. The precipitate was filtered or extracted with EtOAc or CH2C12 and the obtained solid was dried in vacuo or purified by column chromatography or triturated to afford the desired product.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route (4-(Trifluoromethoxy)phenyl)methanamine, its application will become more common.

Reference:
Patent; INDIANA UNIVERSITY RESEARCH AND TECHNOLOGY CORPORATION; ASSEMBLY BIOSCIENCES, INC.; TURNER, William W.; ARNOLD, Lee Daniel; MAAG, Hans; ZLOTNICK, Adam; WO2015/138895; (2015); A1;,
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Application of 171290-52-1, The chemical industry reduces the impact on the environment during synthesis 171290-52-1, name is 3,5-Dimethoxyphenylacetylene, I believe this compound will play a more active role in future production and life.

(S) -3- (5-amino-3-bromo-4-cyano-1H -Pyrazol-1-yl) pyrrolidine-1-carboxylic acid third butyl ester 7c (5g, 14.1mmol), cuprous iodide (0.6g, 2.8mmol), triethylamine (9mL), [1,1′-bis (diphenylphosphino) ferrocene] palladium dichloride (2g, 2.8mmol) And N, N-dimethylformamide (150mL) were heated to 80 C under the protection of argon, and 1-ethynyl-3,5-dimethoxybenzene (14g, 84.5mmol) was added in portions. And stir for 2 hours.After cooling to room temperature, the reaction solution was poured into water and extracted with ethyl acetate (200 mL × 3).The organic phases were combined, dried over anhydrous sodium sulfate, filtered to remove the drying agent, and concentrated under reduced pressure. The residue was purified by silica gel column chromatography (petroleum ether / ethyl acetate = 5/1) to obtain the target product (S) -3- ( 5-amino-4-cyano-3-((3,5-dimethoxyphenyl) ethynyl) -1H-pyrazol-1-yl) pyrrolidine-1-carboxylic acid third butyl ester 7d (5 g, brown oil), yield: 81%.

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, 3,5-Dimethoxyphenylacetylene, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; BEIJING TIANCHENG PHARMA CO., LTD.; CHEN, XIANGYANG; GAO, YINGXIANG; KONG, NORMAN XIANGLONG; (118 pag.)TW2019/38538; (2019); A;,
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Some common heterocyclic compound, 645-36-3, name is 2,2-Diethoxyethanamine, molecular formula is C6H15NO2, 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. HPLC of Formula: C6H15NO2

[00114] To a glass reactor was charged 3,5-dichlorobenzaldehyde. Absolute ethanol was added to the batch slowly (this addition is mildly exothermic) and agitation started. 2,2- Diethoxyethylamine (1.03 equiv) was slowly added to the batch, keeping the batch temperature at 20-78 C. The batch was then heated to 76-78 C for 2 h. GC-MS analysis indicated reactioncompletion (starting material < 1%). The batch was cooled to ambient temperature for work-up. The batch was concentrated in vacuo to a residue and azeotroped with heptanes (x2). The residue was cooled and held at 0-5 C for 12 h to form a suspension. The solids were collected by filtration and the cake was washed with cold (0-5 C) heptanes, and dried under hot nitrogen (45-5 0 C) to afford Compound 2? as a white solid (94% yield). These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 645-36-3, its application will become more common. Reference:
Patent; SARCODE BIOSCIENCE INC.; ZELLER, James, Robert; VENKATRAMAN, Sripathy; BROT, Elisabeth, C.A.; IYER, Subashree; HALL, Michael; WO2014/18748; (2014); A1;,
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Application of 4316-51-2, A common heterocyclic compound, 4316-51-2, name is 4-Methoxytriphenylamine, molecular formula is C19H17NO, 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.

Boron tribromide was added to a dichloromethane solution of 4-methoxytriphenylamine (formula (6)) while cooling, and the mixture was stirred at room temperature for 3 hours to obtain diphenylaminophenol (formula (7) in a yield of 90% It was.

The synthetic route of 4316-51-2 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; YOKOHAMA NATIONAL UNIVERSITY; NAKAGAWA, TETSUYA; YOKOYAMA, YASUSHI; MIYASAKA, YOSUKE; (14 pag.)JP2018/20988; (2018); A;,
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Reference of 707-07-3, These common heterocyclic compound, 707-07-3, name is (Trimethoxymethyl)benzene, 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: 2-Nitroaniline derivative (1 mmol) was added to a mixture of indium powder (574 mg, 5.0 mmol for 2-nitroaniline, 918 mg 8.0 mmol for 1,2-dinitroarene), and acetic acid (0.572 mL, 10 mmol) in ethyl acetate (2 mL), followed by the addition of trimethyl orthoester (2.0 mmol) in ethyl acetate (3 mL for 2-nitroaniline; 8 mL for 1,2-dinitroarene). The reaction mixture was stirred at reflux under a nitrogen atmosphere. After the reaction was completed, the reaction mixture was diluted with ethyl acetate (30 mL), filtered through Celite, poured into 10% NaHCO3 (30 mL), and then extracted with ethyl acetate (30 mL×3). The combined organic extracts were dried over MgSO4, filtered, and concentrated. The residue was eluted with ethyl acetate/hexane (v/v=10/90) for 2-phenylbenzimidazole derivatives or methanol/dichloromethane (v/v=1/99) for 2-methylbenzimidazole derivatives through a silica gel column to give the corresponding benzimidazoles. The structures of the benzimidazoles were characterized by 1H NMR, 13C NMR, FTIR, and GC-MS, and were mostly known compounds. HRMS data were reported in addition for unknown compounds.

Statistics shows that (Trimethoxymethyl)benzene is playing an increasingly important role. we look forward to future research findings about 707-07-3.

Reference:
Article; Kim, Jaeho; Kim, Jihye; Lee, Hyunseung; Lee, Byung Min; Kim, Byeong Hyo; Tetrahedron; vol. 67; 41; (2011); p. 8027 – 8033;,
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