Month: September 2021

Reference of 5905-69-1, 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 5905-69-1 as follows.

A. 2-(4-(difluoromethoxy)phenyl)-4,4,5,5-tetramethyl-l,3,2-dioxaborolaneA mixture of commercially available l-bromo-4-(difluoromethoxy)benzene (1 g, 4.48 mmol), 4,4,4′,4′,5,5,5′,5′-octamethyl-2,2′-bi(l,3,2-dioxaborolane) (1.2g, 4.71 mmol), potassium acetate (1.3 g, 13.4 mmol), and PdCl2(dppf)-CH2Cl2 Adduct (0.18 g, 0.22 mmol) in DMF (15 mL) was stirred under nitrogen at 90 0C for 1 hour. Diluted with DCM, washed with water, sat. NaHCC^, brine, dried (MgSC^), and concentrated.The crude was purified using ISCO flash chromatography (silica gel/ hexanes/ethyl acetate 100:0 to 50:50 gradient) to afford the desired product 2-(4- (difluoromethoxy)phenyl)-4,4,5,5-tetramethyl-l,3,2-dioxaborolane 13A (1.12 g, 3.32 mmol, 74.0 % yield) as a brown oil.

According to the analysis of related databases, 5905-69-1, the application of this compound in the production field has become more and more popular.

Reference:
Patent; BRISTOL-MYERS SQUIBB COMPANY; AHMAD, Saleem; WASHBURN, William, N.; HERNANDEZ, Andres, S.; ROBL, Jeffrey, A.; NGU, Khehyong; WANG, Zhenghua; WO2010/104830; (2010); A1;,
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Adding a certain compound to certain chemical reactions, such as: 18800-30-1, name is 1-Bromo-4-(2-bromoethoxy)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 18800-30-1, Application In Synthesis of 1-Bromo-4-(2-bromoethoxy)benzene

KOr-Bu (14.0 g, 125 mmol) was added in portions over 10 min to l-bromo-4- (2-bromoethoxy)benzene (19.9 g, 100 mmol see step (a) above) in THF (120 mL) at 0 0C. After 16 h at rt, water (400 mL) was added and the mixture was extracted with petroleum ether (4 x 100 mL). The combined extracts were washed with brine, dried (Na2SO4), concentrated and distilled under vacuum to yield the subtitle compound (11.5 g, 58%).

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, 1-Bromo-4-(2-bromoethoxy)benzene, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; BIOLIPOX AB; WO2006/77364; (2006); A1;,
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Related Products of 5414-19-7,Some common heterocyclic compound, 5414-19-7, name is 1-Bromo-2-(2-bromoethoxy)ethane, molecular formula is C4H8Br2O, 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 ethylsulfone acid 833a (2.06 g, 8.79 mmol) in anhydrous THF at-78C under N2 was added LiHMDS solution (19.3 mL, 1.0 Min THF). The mixture was stirred at-78C for 30 min before it was allowed to warmed to 0C along with a cold acetone bath. It was then re-cooled to-78C and to it was added 2-bromoethyl ether (1.8 mL, 13. 2 mmol). After stirred at- 78C for 30 min, the mixture was warmed to rt and stirred for 2 h. It was again re-cooled to-78C and to it was added LiHMDS solution (10.6 mL, 10.6 mmol). After stirred at-78C for 30 min, the mixture was warmed to rt and stirred for 3 h before it was quenched with 1 N aqueous HCI solution until the pH is about 1-2. The solution was extracted with CH2CI2 (2×450 mL). Combined organic solution was dried (MgS04), filtered and concentrated. The crude product was dissolved in 1 N NaOH solution (300 mL) and extracted with EtOAc (100 mL). After layers were separated, the organic solution was washed with 1 N NaOH (2×150 mL). The combined aqueous solution was acidified to pH-1 using 6 N HCI solution. It was extracted with EtOAc (3 x 300 mL). The organic solutions were combined, dried (MgSO4), filtered and concentrated to give 2.3 g product (833b; 7.56 mmol, 89%).

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-(2-bromoethoxy)ethane, its application will become more common.

Reference:
Patent; SCHERING CORPORATION; WO2005/87731; (2005); A1;,
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Reference of 39538-68-6, 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. 39538-68-6, name is 2-Methoxy-4-methylaniline, This compound has unique chemical properties. The synthetic route is as follows.

A solution of 2-methoxy-4-methylaniline (18, 10.9 mmol), bis-(2-chloroethyl)amine hydrochloride (12.0 mmol), potassium carbonate (15.2 mmol) in 1-butanol (5 mL) was refluxed under nitrogen overnight. The hot reaction mixture was filtered and the filtrate was concentrated under vacuum. The resulting residue was triturated with acetone and filtered to give 19 as an off-white powder (14% yield), mp 212-213 C (dec); 1H NMR (free base, CDCl3) delta 9.14 (s, 1H), 6.68-6.82 (m, 3H), 3.77 (s, 3H), 3.11-3.19 (m, 8H), 2.25 (s, 3H).

The chemical industry reduces the impact on the environment during synthesis 2-Methoxy-4-methylaniline. I believe this compound will play a more active role in future production and life.

Reference:
Article; Vangveravong, Suwanna; Zhang, Zhanbin; Taylor, Michelle; Bearden, Melissa; Xu, Jinbin; Cui, Jinquan; Wang, Wei; Luedtke, Robert R.; MacH, Robert H.; Bioorganic and Medicinal Chemistry; vol. 19; 11; (2011); p. 3502 – 3511;,
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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 886762-08-9 as follows. name: 5-Bromo-2-(trifluoromethoxy)aniline

10.74 g (93.75 mmol) of tert-butyl nitrite and 28.5 g (150 mmol) of copper iodide are suspended in 270 ml of acetonitrile and heated to 60 C. A solution of 15 g (62.5 mmol) of 5-bromo-2-trifluoromethoxyaniline in 130 ml of acetonitrile is slowly added dropwise to this suspension and the mixture is left to stir at 60 C. for another hour. The reaction solution is then poured on to a mixture of 250 ml of 2 N aqueous HCl and 250 ml of ethyl acetate. The organic phase is washed twice more with aqueous NaCl solution, filtered through a little silica gel and concentrated. The residue is separated by chromatography on silica gel (ethyl acetate/n-heptane=1/18). This affords 12.2 g (52% yield) of product 96 as a colorless oil.

According to the analysis of related databases, 886762-08-9, the application of this compound in the production field has become more and more popular.

Reference:
Patent; SANOFI-AVENTIS; US2011/59910; (2011); A1;,
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A common compound: 363-47-3, name is 3,5-Difluoro-4-methoxyaniline, belongs to ethers-buliding-blocks compound, it can change the direction of chemical reaction, and react with certain compounds to generate new functional products. A new synthetic method of this compound is introduced below. 363-47-3

Example 19 N-(3,5-difluoro-4-methoxyphenyl)-2-(imidazo[1,2-a]pyridin-5-yl)acetamide (0299) To a mixture of 3,5-difluoro-4-methoxyaniline (54 mg), 2-(imidazo[1,2-a]pyridin-5-yl)acetic acid (50 mg) and anhydrous DMF (1 mL) were added HATU (160 mg) and DIPEA (0.074 mL) at room temperature, and the mixture was stirred at room temperature for 3 days. The reaction mixture was diluted with saturated aqueous sodium hydrogen carbonate solution, and extracted with ethyl acetate. The extract was washed with water and saturated brine, and dried over anhydrous magnesium sulfate. The solvent was evaporated under reduced pressure and the obtained residue was purified by silica gel column chromatography (NH, ethyl acetate/methanol) and recrystallized from ethyl acetate-hexane to give the title compound (46 mg). 1H NMR (300 MHz, DMSO-d6) delta3.86 (3H, s), 4.15 (2H, s), 6.88 (1H, d, J = 6.8 Hz), 7.25 (1H, dd, J = 9.0, 6.8 Hz), 7.35 (2H, d, J = 10.5 Hz), 7.55 (1H, d, J = 9.0 Hz), 7.62 (1H, d, J = 1.1 Hz), 7.85 (1H, s), 10.66 (1H, s).

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, 363-47-3, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; Takeda Pharmaceutical Company Limited; KIMURA, Eiji; MIYANOHANA, Yuhei; OGINO, Masaki; TANAKA, Yuta; FUSHIMI, Makoto; OKAWA, Tomohiro; HANYA, Yuki; KOIKE, Tatsuki; (67 pag.)EP3239150; (2017); A1;,
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Related Products of 627527-23-5, 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. 627527-23-5, name is 1-Bromo-3-methoxy-5-(trifluoromethyl)benzene belongs to ethers-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below.

Step 2: Preparation of 8-[3-methoxy-5-(trifluoromethyl)phenyl]-1,4-dioxa-8- azaspiro[4.5]decane To a mixture of 1-bromo-3-methoxy-5-(trifluoromethyl)benzene (500 mg, 1.96 mmol), 1,4-dioxa-8-azaspiro[4.5]decane (281 mg, 1.96 mmol) and sodium tert-butoxide (377 mg, 3.92 mmol) in dioxane (10 mL) was added Pd2(dba)3 (71.8 mg, 78.4 mumol) and Ruphos (18.3 mg, 39.2 mumol) under N2. The resulting mixture was then heated with stirring at 100oC overnight. After being cooled down to rt, the resulting mixture was diluted with H2O (10 mL) and extracted with EA (30 mL) for three times. The organic layers were combined, dried over anhydrous Na2SO4 and concentrated in vacuo to give crude 8-(3-methoxy-5-(trifluoromethyl)phenyl)-1,4- dioxa-8-azaspiro[4.5]decane (650 mg) which was used in the next step directly without an further purification.

The synthetic route of 1-Bromo-3-methoxy-5-(trifluoromethyl)benzene has been constantly updated, and we look forward to future research findings.

Reference:
Patent; F. HOFFMANN-LA ROCHE AG; HOFFMANN-LA ROCHE INC.; CHENG, Zhanling; HAN, Xingchun; JIANG, Min; WANG, Jianhua; WANG, Min; WANG, Yongguang; YANG, Song; (319 pag.)WO2016/177655; (2016); A1;,
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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. 103-50-4, name is Benzyl ether, This compound has unique chemical properties. The synthetic route is as follows., name: Benzyl ether

General procedure: To a sealed tube containing the respective azobenzene 1 (0.25 mmol), dibenzyl ether 2 (0.75 mmol), Pd(OAc)2 (0.025 mmol), and DCE/AcOH (1:1, v/v, 1 mL in all) was added TBHP (1.5 mmol). After stirring vigorously at 60 C for 12 h, the mixture was evaporated under vacuum. The corresponding product 3 was isolated by silica gel column chromatography with a PE/EtOAc mixture as eluent.

According to the analysis of related databases, 103-50-4, the application of this compound in the production field has become more and more popular.

Reference:
Article; Hong, Gang; Aruma, Alfred Njasotapher; Zhu, Xiaoyan; Wu, Shengying; Wang, Limin; Synthesis; vol. 48; 8; (2016); p. 1147 – 1158;,
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Some common heterocyclic compound, 6298-96-0, name is 1-(4-Methoxyphenyl)ethylamine, molecular formula is C9H13NO, 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: C9H13NO

The solution of 4-oxo-4-(pyridin-2-yl)butanal (326 mg, 2 mmol) in dichloromethane (15 mL) was added NaBH(OAc)3(1.27 g, 6 mmol) and HOAc (20 mg, 0.33 mmol) at -70C. The resulting suspension was stirred at the same temperature for 30 min. The reaction was warmed to 0C and added (5)-l-(4- methoxyphenyl)ethanamine (332 mg, 2.2 mmol). The resulting suspension was stirred at room temperature overnight. The reaction mixture was evaporated and the residue was purified by silica gel column chromatography (petroleum ether/ethyl acetate = 1/10) to give the desired product (400 mg, 71 %) as a red solid. H NMR (400 MHz, CDC13) delta 8.42 (s, 1H), 7.58- 7.45 (m, 1H), 7.35 (d, / = 7.2 Hz, 1H), 7.15 (d, / = 7.6 Hz, 2H), 7.02 (s, 1H), 6.68 (d, / = 8.0 Hz, 2H), 3.91 (s, 1H), 3.74-3.71 (m, 4H), 3.09 (s, 1H), 3.62 (d, / = 7.2 Hz, 1H), 2.26-2.15 (m, 1H), 1.99- 1.89 (m, 1H), 1.76 (s, 2H), 1.34 (d, J = 4.8 Hz, 3H).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 6298-96-0, its application will become more common.

Reference:
Patent; SUZHOU YUNXUAN YIYAO KEJI YOUXIAN GONGSI; ZHANG, Xiaohu; ZHENG, Jiyue; MA, Haikuo; (184 pag.)WO2019/60860; (2019); 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. 450-88-4, name is 1-Bromo-4-fluoro-2-methoxybenzene, A new synthetic method of this compound is introduced below., Quality Control of 1-Bromo-4-fluoro-2-methoxybenzene

10504] Under a nitrogen atmosphere, into a reaction vessel equipped with a dropping flannel were added 1.00 g of 2-bromo-5-fluoroanisole and 20 mE of tetrahydrofuran. The resultant solution was cooled down to -78 C., then, 3.0 mE of n-butyllithium (1.62 Mlhexane solution) was dropped. The resultant mixture was stirred at the same temperature for 3 hours, then, a solution obtained by dissolving 1.00 g of chlorodicyclopentylphosphine in 13 ml of tetrahydroffiran was dropped at -78 C. The resultant mixture was stirred at room temperature for 3 hours. The resultant reaction mixture was concentrated, to obtain 1.75 g of a mixture in the form of viscous liquid containing dicyclopentyl(4-fluoro-2-methox- yphenyl)phosphine.

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; Sumitomo Chemical Company, Limited; ODA, Seiji; KAMIKAWA, Takashi; US2015/322101; (2015); A1;,
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