Category: ethers-buliding-blocks

These common heterocyclic compound, 4393-09-3, name is (2,3-Dimethoxyphenyl)methanamine, 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. name: (2,3-Dimethoxyphenyl)methanamine

Step A. tert-Butyl 4-[(1-{[(2,3-dimethoxybenzyl)amino]carbonyl}-4-piperidinyl)amino]phenethylcarbamate The title compound (0.32 g, 0.64 mmol) was prepared from 2,3-dimethoxy benzyl amine (0.668 g, 4.0 mmol) and {2-[4-(piperidin-4-ylamino)-phenyl]-ethyl}-carbamic acid tert-butyl ester (1.276 g, 4.0 mmol) according to Procedure C.

The synthetic route of (2,3-Dimethoxyphenyl)methanamine has been constantly updated, and we look forward to future research findings.

Reference:
Patent; American Home Products Corporation; US2002/28832; (2002); A1;,
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Related Products of 59557-91-4, The chemical industry reduces the impact on the environment during synthesis 59557-91-4, name is 4-Bromo-2-methoxyaniline, I believe this compound will play a more active role in future production and life.

General procedure: To a solution of 3k (300 mg, 1.48 mmol) in anhydrous CH2C12 (15 mL) was added pyridine (0.24 mL, 2.97 mmol) and 1-propanesulfonyl chloride (0.18 mL, 1.63 mmol) under argon, and the mixture was stirred at room temperature for 16 h. After being quenched with 1 N HC1(aq) (1.0 mL), water, and CH2C12 were added, the layers were separated. The combined organic phases were washed with brine, dried over anhydrous Na2SO4, filtered, and concentrated. The residue was purified by column chromatography on silica gel (EtOAc/hexane, 10:90 to 15:85) to give 6k (490.1 mg, 99%) as a light yellow oil; ?H NMR (CDC13, 500 MHz) 7.41 (1 H, d, J = 8.6 Hz), 7.08 (1 H, dd, J = 8.3, 2.3 Hz), 7.03 (1 H, d, J = 2.5 Hz), 6.74 (1 H, br) , 3.88 (3 H, s), 3.02-2.98 (2 H, m), 1.83-1.79 (2 H, m), 1.00 (3 H, t, J = 7.4 Hz); ?3C NMR (CDC13, 125 MHz) 149.5, 125.5, 124.2, 121.0, 117.5, 114.3, 56.1, 53.1, 17.1, 12.8.

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, 4-Bromo-2-methoxyaniline, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; UNIVERSITY OF HOUSTON SYSTEM; TRUSTEES OF TUFTS COLLEGE; CUNY, Gregory; SUEBSUWONG, Chalada; DEGTEREV, Alexei; (139 pag.)WO2018/183633; (2018); A1;,
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Synthetic Route of 95970-05-1, A common heterocyclic compound, 95970-05-1, name is 2,6-Dibromo-4-methoxyaniline, molecular formula is C7H7Br2NO, 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.

To a solution of 2,6-dibromo-4-methoxyphenylamine (3 g, 10.67 mmol, 1 eq) in 10 ml of toluene cooled at 0° C. are added 6.6 ml of concentrated sulfuric acid and 17.5 ml of H3PO2 50percent (15 eq). To the reaction mixture, sodium nitrite (1.47 mg, 21.35 mmol, 2 eq) is added, and all is stirred at 0° C. for 4.5 h. After neutralization with a sodium hydroxide solution, extraction with diethyl ether is performed. The organic phase is dried over magnesium sulfate, filtered and evaporated to dryness on a rotary evaporator. Purification of the raw product was not necessary (yield 96percent, 2.7 g). C7H6Br2O; MW 264/266/268; 1H-NMR (CDCl3): delta 7.23-7.22 (m, 1H), 6.97 (s, 1H), 6.96 (s, 1H), 3.75 (s, 3H); 13C-NMR: delta 160.8, 126.4, 123.1, 116.5, 55.7; IR: 2925, 1599, 1569, 1464 1/cm

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; Hartmann, Rolf; Frotscher, Martin; Oberwinkler, Sandrine; Ziegler, Erika; Messinger, Josef; Thole, Heinrich-Hubert; US2010/204234; (2010); A1;,
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Related Products of 104197-14-0, A common heterocyclic compound, 104197-14-0, name is 4-Bromo-2,6-difluoroanisole, molecular formula is C7H5BrF2O, 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 4 2.5-Difluoro-4-methoxy-benzaldehyde A mixture of 4-bromo-2,6-difluoroanisole (4.46 g, 20.0 mmol), toluene (200 mL), and THF (10 mL) was cooled to -78 C. To the mixture was added n-BuLi (8.00 mL of a 2.5 M solution in hexanes, 20 mmol). After stirring at -78 C. for 1 h, DMF (3.10 ml, 40.0 mmol) was added. The mixture was stirred at -78 C. for 2 h and then H2O (100 mL) was added. After warming to rt, the mixture was extracted with EtOAc (2*75 mL). The combined extracts were dried (MgSO4), filtered and concentrated to provide 3.00 g of 2,5-difluoro-4-methoxy-benzaldehyde as a solid. 1H NMR (400 MHz, CDCl3): delta 10.18 (d, 1, J=2.9), 7.54 (dd, 1, J=10.6, 6.4), 6.72 (dd, 1, J=11.4, 6.4), 3.95 (s, 3).

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; Pfizer Inc; US2006/58361; (2006); 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., category: ethers-buliding-blocks

Example 111 Preparation of 4-phenoxyphenyl-phenylmethanol (127) To a stirred solution of 4-bromodiphenyl ether (2.0 g, 8.03 mmol) in THF (15 mL) at -78 C. was added n-butyllithium (3.85 mL, 2.6 M solution in hexanes). The reaction was stirred under argon for 2 hrs before a solution of benzaldehyde (0.85 g, 8.03 mmol) in THF at -78 C. was added. After stirring at -78 C. for 2 hrs, the reaction was quenched with water and extracted with ether. The organic layer was washed with brine, dried over magnesium sulfate, filtered, and concentrated under reduced pressure to give the crude product. The crude mixture was purified via flash SiO2 chromatography (ethyl acetate/hexanes (10%/90%) to (15%/85%)) to give 127 (2.22 g, 97% yield): 1H-NMR (400 MHz, chloroform-d) delta 7.28-7.40 (m, 9H), 7.10 (t, J=7.6, 1 H), 6.94-7.01 (m, 4H), 5.84 (d, J=3.6 Hz, 1H), 2.17 (d, J=3.6 Hz, 1H).

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; Scanlan, Thomas S.; Hart, Matthew E.; Grandy, David K.; Bunzow, James R.; Miyakawa, Mononori; Tan, Edwin Saavedra; Suchland, Katherine L.; US2005/96485; (2005); A1;,
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Reference of 1758-46-9,Some common heterocyclic compound, 1758-46-9, name is 2-Phenoxyethylamine, molecular formula is C8H11NO, 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 2-phenoxy-ethylamine (5 eq.) or 2-(2-methoxyphenoxy-)ethylamine (5 eq.) in 2-methoxyethanol(25 mL per mmol of amine) the appropriate aliphatic chloride33-39 (1 eq.) and KI (cat.) was added. The mixturewas refluxed for18-48 h and concentrated. The residue was suspended in CHCl3and washed with 1M NaOH, brine, dried over anhydrous Na2SO4and concentrated. The crude was purified by flash chromatographyto give the titled compound.

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

Reference:
Article; Franchini, Silvia; Sorbi, Claudia; Linciano, Pasquale; Carnevale, Gianluca; Tait, Annalisa; Ronsisvalle, Simone; Buccioni, Michela; Del Bello, Fabio; Cilia, Antonio; Pirona, Lorenza; Denora, Nunzio; Iacobazzi, Rosa Maria; Brasili, Livio; European Journal of Medicinal Chemistry; vol. 176; (2019); p. 310 – 325;,
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Synthetic Route of 41365-75-7, 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 41365-75-7 as follows.

General procedure: To a solution of 2.05 g (14 mmol) of 3,3-diethoxypropan-1-amine 3 and 2.83 g (28 mmol) of triethylamine in 15 ml of benzene 14 mmol of N,N-di(alkyl, aryl)carbamoyl chloride was added dropwise at cooling (5-7 C). The reaction mixture was stirred under cooling for 2 hours. The precipitate was filtered off, the filtrate was evaporated in vacuum to give the target compound 4 as a yellow oil, which was used in subsequent reactions without further purification.

According to the analysis of related databases, 41365-75-7, the application of this compound in the production field has become more and more popular.

Reference:
Article; Smolobochkin, Andrey V.; Gazizov, Almir S.; Burilov, Alexander R.; Pudovik, Michail A.; Synthetic Communications; vol. 48; 19; (2018); p. 2545 – 2552;,
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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. 67191-35-9, name is 1-Isopropoxy-2-vinylbenzene belongs to ethers-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below. name: 1-Isopropoxy-2-vinylbenzene

General procedure: The product was synthesized using in-situ generated Grubbs-Hoeyda 2nd generation catalyst.Therefore Grubbs 2nd generation catalyst (0.1 mmol, 0.02 equiv.) was dissolved in drydichloromethane (5 mL), 1-Isopropoxy-2-vinylbenzene (0.1 mmol, 0.02 equiv.) and copper(I)chloride(0.1 mmol, 0.02 equiv.) were added and the reaction mixture was stirred at reflux for 45 min until thecolour turned green. After cooling to room temperature VCP XX (5 mmol, 1 equiv.) and methylacrylate (30 mmol, 6 equiv.) were added and the reaction mixture was stirred at reflux for 16 h, afterwhich additional methyl acrylate (10 mmol, 2 equiv.) was added and stirred for another 7 h at reflux.The product was obtained via column chromatography on silica gel (5:1 petroleum ether/ethylacetate) as a white powder

The synthetic route of 67191-35-9 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Pursley, Dominik; Plietker, Bernd; Synlett; vol. 25; 16; (2014); p. 2316 – 2318;,
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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 7252-83-7 as follows. Quality Control of 2-Bromo-1,1-dimethoxyethane

To a suspension of 2-amino-3,5-dibromopyrazine (2 g, 7.91 mmol) in water (25 mL) was added 2-bromo-1,1-dimethoxyethane (0.96 mL, 8.15 mmol, 1.03 equiv.) and the reaction mixture was heated at 100C for 2h. The reaction mixture was then cooled down to r.t. and the resulting precipitate was collected by filtration and dried under reduced pressure overnight to afford the title product as a beige solid (2 g, 7.22 mmol, 91 %) that was used without further purifi25 cation. ESI-MS: 275.95/277.95/279.95 [M+H]+.

According to the analysis of related databases, 7252-83-7, the application of this compound in the production field has become more and more popular.

Reference:
Patent; SELVITA S.A.; BOBOWSKA (NEE WITKOWSKA), Aneta; GALEZOWSKI, Michal; NOWAK, Mateusz; COMMANDEUR, Claude; SZEREMETA-SPISAK, Joanna; NOWOGRODZKI, Marcin; OBARA, Alicja; DZIELAK, Anna; LOZINSKA, Iwona; DUDEK (NEE SEDLAK), Marcelina; JANIGA, Anita; REUS, Jacek; WRONOWSKI, Marek; ZASTAWNA, Magdalena; RADZIMIERSKI, Adam; SWIRSKI, Mateusz; ZACHMANN, Julian; FABRITIUS, Charles-Henry; PORTER, Rod; FOGT, Joanna; (276 pag.)WO2019/2606; (2019); A1;,
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Some common heterocyclic compound, 22236-08-4, name is 3-(Difluoromethoxy)aniline, molecular formula is C7H7F2NO, 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. Application In Synthesis of 3-(Difluoromethoxy)aniline

General procedure: Atwo neck round bottom flask under argon equipped with a condenser was chargedwith aldehyde 4 (1.0 mmol, 1.0 equiv.)and 4-chloroaniline 3b (1.1 mmol, 1.1equiv.) in 2-pentanol (3.3 mL, 0.3 M) and stirred at reflux for two hours. Thetetronic acid 5 (1.1 mmol, 1.1 equiv.)in 2-pentanol (0.8 mL) was then added at reflux, after 10 mins. The thirdcomponent aniline 3 (1.0 mmol, 1.0 equiv.)was added dropwise and was refluxed for 30 min. The solvent was evaporated under vacuum and theproduct purified by recrystallization in ethanol (5.0 mL) or by flashchromatography

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 22236-08-4, its application will become more common.

Reference:
Article; Jeedimalla, Nagalakshmi; Johns, Jennifer; Roche, Stephane P.; Tetrahedron Letters; vol. 54; 44; (2013); p. 5845 – 5848;,
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