Month: June 2021

Application of 1978-39-8, The chemical industry reduces the impact on the environment during synthesis 1978-39-8, name is 5-Fluoro-2-methoxyaniline, I believe this compound will play a more active role in future production and life.

Step (c): Preparation of 1-(3-fluoro-6-methoxyphenyl)piperazine 5-fluoro-2-methoxyaniline (0.092 mol) and bis(2-chloroethyl)aminehydrochloride (0.1 mol) in xylene (300 ml) was refluxed with stirring for a period of 20 hrs. Water was added to the reaction and the organic layer discarded. The aqueous layer was basified with sodium hydroxide and extracted with methylene chloride (2*100 ml). The methylene chloride extract was dried (sodium carbonate), filtered, and concentrated. Residual material was distilled to provide 8.8 g (45% yield) of piperazine product, b.p. 111-114 C. 0.15 mmHg:

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, 5-Fluoro-2-methoxyaniline, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; Bristol-Myers Company; US4585773; (1986); A;,
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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. 7664-66-6, name is 4-Isopropoxyaniline, This compound has unique chemical properties. The synthetic route is as follows., HPLC of Formula: C9H13NO

General procedure: N,N’-di(2-fluorophenyl)-4-methoxyl-isophthalamide(1a): Equipped a stirrer in a three-necked flask (100 ml), to a mixture of 2-fluoroaniline (1.11 g, 10.0 mmol),anhydrous tetrahydrofuran (15 ml) and dry pyridine (1 ml), dropwise added 4-methoxyl-isophthaloyl dichloride (1.17 g, 5.0 mmol) which had been dissolved in dry tetrahydrofuran (10 ml). After the mixture reaction at room temperature for 8 h under continuous stirring, the excess tetrahydrofuran was distilled off in vacuum. The residue was recrystallized by acetone. Its melting point is 204-206 C, and yield is 67%. The other compounds 1b-1j, 2a-2k, 3a-3l and 4a-4h were prepared in the same manner.

According to the analysis of related databases, 7664-66-6, the application of this compound in the production field has become more and more popular.

Reference:
Article; Liu, Xiu Jie; Shi, Xin Xin; Zhong, Yong Liang; Liu, Ning; Liu, Kai; Bioorganic and medicinal chemistry letters; vol. 22; 21; (2012); p. 6591 – 6595,5;,
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Synthetic Route of 202865-80-3, 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. 202865-80-3, name is 4-Bromo-2-fluoro-1-isopropoxybenzene belongs to ethers-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below.

To a mixture of 5-amino-3-t-butyl-1-(4-chlorobenzyl)pyrazole (50.0 mg, 0.190 mmol) and dioxane (1 mL) were added 4-bromo-2-fluoro-1-isopropoxybenzene (49 mg, 0.21 mmol), tris(dibenzylideneacetone)(0) (2.2 mg, 0.0024 mmol), 4,5-bis(diphenylphosphino)-9,9-dimethylxanthene (3.3 mg, 0.0057 mmol) and sodium phenoxide trihydrate (48 mg, 0.28 mmol), and the resulting mixture was stirred at 170C for 30 minutes under microwave irradiation. To the reaction mixture was added saturated aqueous sodium bicarbonate, and the mixture was extracted with ethyl acetate. The extract was washed by brine, dried over anhydrous sodium sulphate, and concentrated in vacuo. The resulting residue was purified by silica gel column chromatography (ethyl acetate/hexane) and reversed-phase HPLC (0.3%fomic acid/acetonitrile) to give 3-t-butyl-1-(4-chlorobenzyl)-5-(3-fluoro-4-isopropoxyphenylamino)pyrazole (33 mg, Yield: 42%) as pale yellow solid. 1H-NMR (delta ppm TMS/DMSO-d6): 1.20-1.24 (15H, m), 4.30-4.37 (1H, m), 5.18 (2H, s), 5.92 (1H, s), 6.53-6.65 (2H, m), 6.96 (1H, t, J = 9.0 Hz), 7.06 (2H, d, J = 8.1 Hz), 7.34 (2H, d, J = 8.1 Hz), 7.91 (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, 4-Bromo-2-fluoro-1-isopropoxybenzene, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; Shionogi & Co., Ltd.; KAI, Hiroyuki; ENDOH, Takeshi; JIKIHARA, Sae; ASAHI, Kentaro; HORIGUCHI, Tohru; EP2604260; (2013); A1;,
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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.

Add methyl 2-[(£’)-2-(dimethylamino)vinyl]-5-nitro-benzoate (2.4 Kg crude, 9.65 mol), 2,4-dimethoxybenzylamine (2.14 Kg, 12.8 mol) and toluene (30 L). Heat the mixture to 95-100 C and stir at that temperature for 16 hours. Cool to 20-25 C and collect the precipitated solid by filtration. Dry the yellow solid in the air for two days to give the crude product (2.17 Kg, 66%) which is used without further purification. ES/MS (m/z): 341.1 (M+H).

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

Reference:
Patent; ELI LILLY AND COMPANY; BROOKS, Harold Burns; DALLY, Robert Dean; DURHAM, Timothy Barrett; FALES, Kevin Robert; FRIMPONG, Kwame; MCCOWAN, Jefferson Ray; NJOROGE, Frank George; SHEPHERD, Timothy Alan; SI, Chong; THRASHER, Kenneth Jeff; TOTH, James Lee; WU, Zhipei; (106 pag.)WO2016/89670; (2016); A1;,
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These common heterocyclic compound, 1535-73-5, name is 3-Trifluoromethoxyaniline, 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. category: ethers-buliding-blocks

Preparation of A/-(3-(5-(3-(trifluoromethoxy)phenylamino)pyridin-3- vDphenvDacetamide (Compound 152) [00296] A mixture of 3,5 -dibromopyridine (2.0Og, 8.44mmol), 3-acetamidophenylboronic acid (1.5 Ig, 8.44mmol), potassium carbonate (1.17g, 8.44mmol) and palladium (tetrakis)triphenylphosphine (294mg, 0.025mmol) in DME/H20 (4OmL, 3:1) was refluxed for 16h. The solvent was removed in vacuo, the resulting yellow solid was partitioned between DCM (30OmL) and brine (15OmL) and the two layers were separated. The aqueous layer was extracted further with DCM (2x10OmL) and the combined extracts were dried over anhydrous MgSO4. Evaporation of the solvent afforded crude iV-(3-(5-bromopyridin-3- yl)phenyl)acetamide in 74percent purity (LC). This material (1.2Og, 4.12mmol), 3- (trifluoromethoxy)aniline (66IuL, 4.95mmol), cesium carbonate (3.36g, 10.3mmol), palladium bis-acetate (47mg, 0.21mmol) and Xantphos (238mg, 0.41mmol) were dissolved in dioxane (7.5mL) and the resulting mixture was heated, under microwave activation, at 15O0C for 20mins. The crude mixture was partitioned between EtOAc (10OmL) and brine (10OmL) and the two layers were separated. The aqueous layer was extracted further with EtOAc (10OmL), the combined layers were dried over anhydrous MgSO4 and evaporated to dryness. The resulting solid was purified by column chromatography eluting using a gradient (EtOAc/hexanes 0:1 v/v to EtOAc/hexanes 1 :0 v/v) to afford 590mg (37percent) of the title compound. LCMS RT= 1.59min, MH+ 388.2. 1U NMR (d6-DMSO): 10.07 (IH, s), 8.83 (IH, s), 8.39 (IH, d, J2.5), 8.36 (IH, d, J 1.9), 7.91 (IH, s), 7.65 (IH, t, J2.2), 7.60 (IH, d, J 8.0), 7.45-7.33 (3H, m), 7.17 (IH, dd, J 8.2 1.8), 7.02 (IH, s), 6.84 (IH, d, J 8.2), 2.07 (3H, s).

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

Reference:
Patent; BioMarin IGA, Ltd.; WREN, Stephen Paul; WYNNE, Graham Michael; LECCI, Cristina; WILSON, Francis Xavier; DAVIS, Paul James; WO2010/57833; (2010); A1;,
Ether – Wikipedia,
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These common heterocyclic compound, 82830-49-7, name is 2-Fluoro-1,4-dimethoxybenzene, 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. Application In Synthesis of 2-Fluoro-1,4-dimethoxybenzene

To a solution of 2-fluoro-l,4-dimethoxybenzene (8.1 g, 52.0 mmol) in anhydrous THF at -78 C, n-BuLi (2.5 M in hexane, 22 mL, 55 mmol) was added dropwise. The resulting mixture was stirred at -78 C for 1 h, and then ethyl chloroformate (5 mL, 52.1 mmol) was added dropwise. The reaction mixture was stirred at -78 C for additional 2 h and quenched with water (200 mL). The mixture was extracted with ethyl acetate (2×180 mL). The combined organic layers were washed with brine (200 mL), dried (Na2S04), and concentrated in vacuo. The residue was purified by silica gel column chromatography (1 :5 EtOAc/petroleum ether) to give ethyl 2-fluoro-3,6-dimethoxybenzoate (8.1 g).

The synthetic route of 2-Fluoro-1,4-dimethoxybenzene has been constantly updated, and we look forward to future research findings.

Reference:
Patent; ARAGON PHARMACEUTICALS, INC.; KAHRAMAN, Mehmet; GOVEK, Steven, P.; NAGASAWA, Johnny, Y.; SMITH, Nicholas, D.; WO2011/156518; (2011); A2;,
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Adding a certain compound to certain chemical reactions, such as: 60876-70-2, name is 1-Bromo-4-(tert-butoxy)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 60876-70-2, Safety of 1-Bromo-4-(tert-butoxy)benzene

Compound (T-22) (179.7 g, 784.5 mmol), bispinacolato diborane (239.0 g, 941.4 mmol), potassium acetate (92.4 g, 941.4 mmol), bis(diphenylphosphino ferrocene dichloropalladium(II) (10.0 g, 13.7 mmol) and 1,3-dioxane (1,000 mL) were mixed, and the resulting mixture was stirred at 90 C. for 4 hours. The reaction mixture was allowed to cool to room temperature, and then poured into water, and subjected to extraction with heptane (800 mL). The extracted layer was washed with water (1,000 mL) and saturated brine (500 mL), dried over anhydrous magnesium sulfate, and concentrated under reduced pressure. The residue was purified by column chromatography (eluent:heptane) to obtain compound (T-23) (182 g, 659 mmol, 84.10).

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:
Patent; JNC Co., Ltd.; JNC Petrochemical Co., Ltd.; Kobayashi, Masahide; Goto, Yasuyuki; Goto, Mayumi; (103 pag.)KR2016/2826; (2016); A;,
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588-96-5, name is p-Bromophenetole, belongs to ethers-buliding-blocks compound, is considered to be a conventional heterocyclic compound, which is widely used in drug synthesis. The chemical synthesis route is as follows. Product Details of 588-96-5

Example XIV.1 2-{4-[1-(4-Ethoxy-phenyl)-piperidin-4-yl]-phenyl}-propionic acid 1.00 g (4.04 mmol) 2-(4-Piperidin-4-yl-phenyl)-propionic acid methyl ester (XI.3) are added to a mixture of 813 mg (4.04 mmol) 1-bromo-4-ethoxy-benzene, 1.60 g (97%, 16.2 mmol) sodium tert-butyrat, 483 mg (1.62 mmol) 2-(di-tert-butylphosphino)biphenyl and 370 mg (0.40 mmol) tris-(dibenzylidenaceton)-dipalladium(0) in 10 mL 1,4-dioxane. The mixture is stirred for 12 h at 70 C. After that time, the precipitate is filtered off and washed with ACN and diethyl ether. The residue is purified by HPLC (column: Waters XBridge 50; eluent A: water+0.3% NH4OH, eluent B: MeOH) to yield the desired product. C22H27NO3 (M=353.5 g/mol) ESI-MS: 354 [M+H]+Rt (HPLC): 1.69 min (method C)

The synthetic route of 588-96-5 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; ROTH, Gerald Juergen; FLECK, Martin; LEHMANN-LINTZ, Thorsten; NOSSE, Bernd; US2013/143876; (2013); 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. 6298-96-0, name is 1-(4-Methoxyphenyl)ethylamine, A new synthetic method of this compound is introduced below., category: ethers-buliding-blocks

B) (4S)-Lambda/-((1 S)-1-r4-(methyloxy)phenyllethyll-3.4-dihvdro-2H-pyranor3.2-lpyridin-4- amine: To a solution of crude 2,3-dihydro-4/-/-pyrano[3,2-]pyridin-4-one (2.43 g) in 1 ,2- dichloroethane was added {(1S)-1-[4-(methyloxy)phenyl]ethyl}amine EPO (2.49 g, 16.5 mmol) and acetic acid (1.4 ml_, 24.5 mmol). The reaction mixture was stirred for 1 hour, then sodium triacetoxyborohydride (5.18 g, 24.4 mmol) was added. The reaction mixture was stirred at room temperature for 16 hours, then diluted with dichloromethane and quenched with saturated aqueous sodium bicarbonate solution. The organic layer was separated and dried over sodium sulfate. Filtration and concentration, followed by flash chromatography (0 to 10% aqueous NH4OH in acetonitrile) provided (4S)- Lambda/-{(1S)-1-[4-(methyloxy)phenyl]ethyl}-3,4-dihydro-2/-/-pyrano[3,2-/j]pyridin-4-amine (1.90 g, 38% two step yield) as a brown oil. 1H NMR (400 MHz, CDCI3) delta 8.15 (dd, J = 3.0, 3.0 Hz, 1 H), 7.35 (d, J = 8.6 Hz, 2 H), 7.07 (d, J = 2.8 Hz, 2 H), 6.86 (d, J = 8.7 Hz, 2 H), 4.19 (ddd, J = 11.0, 7.7, 3.3 Hz, 1 H), 4.07 (q, J = 6.5 Hz, 1 H), 4.00 (ddd, J = 11.1 , 7.3, 3.5 Hz, 1 H), 3.91 (t, J = 5.7 Hz, 1 H), 3.80 (s, 3 H), 2.32 (br, 1 H), 1.70 (m, 2 H), 1.44 (d, J = 6.6 Hz, 3 H).

The synthetic route of 6298-96-0 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; SMITHKLINE BEECHAM CORPORATION; WO2006/76131; (2006); A2;,
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Synthetic Route of 349-65-5,Some common heterocyclic compound, 349-65-5, name is 2-Methoxy-5-(trifluoromethyl)aniline, 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.

5-(Trifluoromethyl)-2-methoxyaniline was treated with CDI, followed by 4-(1-oxoisoindolin-5-yloxy)aniline according to Method C2d to afford the urea. Entry 26: 4-Hydroxyacetophenone was reacted with 4-fluoronitrobenzene according to Method A13, Step 1 to give 4-(4-acetylphenoxy)nitrobenzene.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 2-Methoxy-5-(trifluoromethyl)aniline, its application will become more common.

Reference:
Patent; BAYER CORPORATION; US2003/144278; (2003); A1;,
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