Category: ethers-buliding-blocks

Related Products of 2106-18-5, These common heterocyclic compound, 2106-18-5, name is 2-(Trifluoromethoxy)fluorobenzene, 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 500 mL three-necked flask, concentrated sulfuric acid (20 mL, 0.35 mol, 3.5 eq)The raw material o-fluorotrifluoromethoxybenzene (18 g, 0.1 mol, 1 eq) was added portionwise with stirring,After stirring for half an hour the solution is clear,Cool to -5 C with ice-salt bath,Concentrated nitric acid (6.6 mL, 0.1 mol, 1 eq) was slowly added dropwise,The reaction is exothermic, the dropping rate to maintain the internal temperature does not exceed 0 ,After the addition is completed,After stirring at 0 C for 1 hour,Heated to 40 C and stirred for 12h,After the reaction solution was cooled to room temperature,Slowly poured into crushed ice, and constantly stirring,A large number of yellow solid precipitation, suction filtration,The filter cake was washed three times with water, drained,Dried under vacuum to give a yellow solid 18g, yield 80%, HPLC purity 95%.

The synthetic route of 2106-18-5 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Wuxi Jiehua Pharmaceutical Technology Co., Ltd.; Bao Liang; Gu Shuyin; (7 pag.)CN106986886; (2017); A;,
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Application of 92028-21-2, As we all know, there are many different methods for the synthesis of a compound, and people can choose the synthesis method that suits their own laboratory according to the actual situation. 92028-21-2 name is 6-Methoxy-[1,1′-biphenyl]-3-amine hydrochloride, This compound is widely used in many fields, so it is necessary to find a new synthetic route. The downstream synthesis method of this compound is introduced below.

Example 6 N-(4-Methoxy-3-phenyl)phenyl-(2-chloro-5-nitrophenyl)carboxamide The title compound (0.586 g) was obtained as a crystalline solid according to the procedure described in Example 2 using (4-methoxy-3-phenyl)aniline hydrochloride (0.478 g), pyridine (5 ml) and 2-chloro-5-nitrobenzoyl chloride (0.535 g). 1H-NMR (400 MHz, CDCl3, TMS): delta(ppm) 3.95 (3H, s), 7.31-7.46 (4H, m), 7.63-7.69 (3H, m), 8.27 (1H, dd, J=8.8, 2.7 Hz), 8.67 (1H, d, J=2.7 Hz), 8.54 (1H, d, 2.2 Hz).

At the same time, in my other blogs, there are other synthetic methods of this type of compound, 6-Methoxy-[1,1′-biphenyl]-3-amine hydrochloride, and friends who are interested can also refer to it.

Reference:
Patent; SANKYO COMPANY, LIMITED; US2003/134859; (2003); A1;,
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Synthetic Route 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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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. 126940-10-1, name is 1-Fluoro-3-(methoxymethoxy)benzene, This compound has unique chemical properties. The synthetic route is as follows., category: ethers-buliding-blocks

To a solution of n-BuLi (76.85 ml_, 192.122 mmol, 1 eq) in THF (300 ml_) was added TMEDA (29.89 ml_, 99.807 mmol, 1 .04 eq) cooled to – 78C and stirred for 1 h. 1 -Fluoro-3-(methoxymethoxy)benzene (30 g, 192.122 mmol, 1 eq) in THF (75 ml_) was added to the mixture dropwise under argon, then the reaction mass was stirred for 2 hr at -78C, followed by addition of trimethylborate at the same temperature then slowly warmed to rt and stirred for 16 h. Then the reaction mass was cooled to 0C, then 30% H202 (18 mL) solution was added slowly dropwise. The reaction mass was warmed to rt and stirred for 1 h. TLC analysis indicated formation of a polar spot. The reaction mixture was dissolved in EtOAc (300 mL) and washed with brine (2×50 mL) and water (2×50 mL). The separated organic layer was dried over Na2S04 and concentrated under reduced pressure to afford crude product; which was purified by column chromatography (silica gel, 100-200mesh) using 8% EtOAc in petroleum ether as an eluent to afford 2-fluoro-6-(methoxymethoxy)phenol (25 g, 75.55%) as a colorless oil.

Chemical properties determine the actual use. Each compound has specific chemical properties and uses. We look forward to more synthetic routes in the future to expand reaction routes of 126940-10-1.

Reference:
Patent; ONTARIO INSTITUTE FOR CANCER RESEARCH (OICR); AL-AWAR, Rima; ISAAC, Methvin; CHAU, Anh My; MAMAI, Ahmed; WATSON, Iain; PODA, Gennady; SUBRAMANIAN, Pandiaraju; WILSON, Brian; UEHLING, David; (191 pag.)WO2019/119145; (2019); A1;,
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Reference of 13985-15-4, As we all know, there are many different methods for the synthesis of a compound, and people can choose the synthesis method that suits their own laboratory according to the actual situation. 13985-15-4 name is 2,3,6,7-Tetramethoxy-9,10-dimethylanthracene, This compound is widely used in many fields, so it is necessary to find a new synthetic route. The downstream synthesis method of this compound is introduced below.

General procedure: To a gently refluxing solution of the anthracene (1a-1c) (1mmol) in 1,2-dichloroethane (50mL) was added portionwise 5-nitrobenzenediazonium-2-carboxylate (2.5mmol). When TLC showed that the starting anthracene was consumed, the reaction mixture was concentrated under reduce pressure. The residue was purified by flash column chromatography on silica gel with petroleum ether: CH2Cl2=4:1 (v/v) as eluent to yield the triptycene as a pale yellow solid. 2b: 67mg, 15% yield. 1H NMR (300MHz, CDCl3): delta 8.08 (s, 1H), 7.87 (d, 1H, J=6.9Hz), 7.37 (d, 1H, J=8.2Hz), 6.98 (s, 2H), 6.97 (s, 2H), 3.86 (s, 12H), 2.46 (s, 3H), 2.43 (s, 3H). 13C NMR (75MHz, CDCl3): delta 156.4, 151.2, 146.3, 146.2, 145.1, 140.4, 139.9, 120.9, 120.4, 115.0, 106.2, 106.0, 56.42, 56.38, 48.5, 48.3, 13.9, 13.7. EI-TOF-MS: m/z 447 [M]+. Anal. calcd. for C26H25NO6·0.1CH2Cl2: C, 68.75; H, 5.57; N, 3.07. Found: C, 68.81; H, 5.80; N, 2.97.

At the same time, in my other blogs, there are other synthetic methods of this type of compound, 2,3,6,7-Tetramethoxy-9,10-dimethylanthracene, and friends who are interested can also refer to it.

Reference:
Article; Li, Peng-Fei; Han, Ying; Chen, Chuan-Feng; Chinese Chemical Letters; vol. 26; 7; (2015); p. 839 – 842;,
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Related Products of 1036724-54-5, 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 1036724-54-5 as follows.

Six reactions were carried out in parallel and combined for work-up. To a solution of the product of the previous step (200 g, 711 mmol) in 15 THF (100 mL) was added 11 potassium carbonate (197 g, 1.4 mol). The reaction mixture was purged with nitrogen 3 times, followed by addition of Pd(dppf)Cl2-CH2Cl2 (11.6 g, 14.2 mmol). The reaction mixture was cooled to 0 C., diethylzinc (1 M, 1.07 L) was added drop-wise, and the reaction mixture was stirred at 70 C. for 1 h. The reactions were combined, cooled to 20 C. and poured into water (7 L) slowly. To the mixture was added aq. 4 M 16 HCl to pH 6. The organic layer was separated, and the aqueous phase was extracted with EtOAc (3×2 L). The combined organic layer was washed with brine (5 L), dried over sodium sulfate, concentrated, and purified through a silica gel pad (eluted with 50:1 17 petroleum ether:EtOAc)) to give the title intermediate (900 g, 92% yield) as a light yellow 18 oil. 1H NMR (400 MHz, CDCl3) delta 7.29-7.43 (m, 5H), 6.94-6.97 (m, 1H), 6.82 (d, J=8.0 Hz, 1H), 6.70 (m, 1H), 5.09 (s, 2H), 2.52-2.58 (m, 2H), 1.17 (t, J=7.6 Hz, 3H).

According to the analysis of related databases, 1036724-54-5, the application of this compound in the production field has become more and more popular.

Reference:
Patent; THERAVANCE BIOPHARMA R&D IP, LLC; FATHEREE, PAUL R.; JIANG, LAN; MCKINNELL, ROBERT MURRAY; THALLADI, VENKAT R.; ZHANG, HAO; DABROS, MARTA; NZEREM, JERRY; BENJAMIN, NOAH; KLEINSCHEK, MELANIE A.; CRATER, GLENN D.; (40 pag.)US2018/311255; (2018); A1;,
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Synthetic Route of 13024-17-4,Some common heterocyclic compound, 13024-17-4, name is N-Methyl-3-phenoxyaniline, molecular formula is C13H13NO, 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: S7 (0.35 g, 2 mmol) was dissolved in Et2O (5 mL) and converted into its hydrochloride salt by drop-wise addition of aq. HCl (1 M) in Et2O. The resulting precipitate was collected byfiltration, dried for 10 min, and used in the subsequent reaction. A mixture of S7 hydrochloride (212 mg, 1 mmol), S1 (185 mg, 1.1 mmol), and toluene (2 mL) was heated to 130 oC,stirred for 21 h, cooled to rt, and diluted with MeOH (5 mL). This solution was concentrated onto silicagel and purified on a silica gel column with gradient elution (EtOAc EtOAc-MeOH;4: 1 v/v). The fractions containing the desired guanidine were collected, concentrated under reduced pressure, andapplied to a second silica gel column eluted with Et3N-EtOAc-hexanes(5: 20: 75 by vol.) to afford 20 asa white solid

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route N-Methyl-3-phenoxyaniline, its application will become more common.

Reference:
Article; Naumiec, Gregory R.; Cai, Lisheng; Pike, Victor W.; Bioorganic and Medicinal Chemistry Letters; vol. 25; 2; (2015); p. 225 – 228;,
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Application of 2338-54-7, A common heterocyclic compound, 2338-54-7, name is 4-Fluoro-3-methylanisole, molecular formula is C8H9FO, 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.

The 4-fluoro-3-methylanisole (7.32 g, 52.28 mmol) was dissolved in 30 ml of carbon tetrachloride. To this solution was added N-bromosuccinimide (9.772 g, 1.05 eq) and A1 EN 428 mg, 5% eq). The mixture was refluxed for 1 hr and then cooled. The solid was filtered out and the filtrate was evaporated. The residue was extracted with ethyl acetate and washed with concentrated sodium bicarbonate. The organic layer was dried and solvents were removed to give an oil (13.0 g). The crude oil was dissolved in 150 ml of ethanol and sodium cyanide (12.8 g, 261 mmol) was added followed by the addition of water (20 ml). The mixture was refluxed for 2.5 hrs. The insoluble material was filtered out and the filtrate was concentrated. The residue was extracted with water and ether. The organic layer was dried and solvents were evaporated to give an oil (8.0 g). This oil was dissolved in 120 ml of ethanol. To that solution was added water (40 ml) and solid sodium hydroxide (20.9 g, 10.0 eq). The mixture was refluxed overnight to give a clear solution. Solvents were evaporated and the residue was suspended in 200 ml of hot water. The solution was cooled down and extracted with ether twice. The aqueous layer was acidified with 6N hydrochloric acid and then extracted with ether. The organic layer was washed with brine and dried. After the evaporation of solvents, 2-fluoro-5-methoxyphenylacetic acid was obtained (6.56 g, 68% in three steps).

The synthetic route of 2338-54-7 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; F. HOFFMANN-LA ROCHE AG; WO2004/101528; (2004); A2;,
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Application of 1236000-51-3, A common heterocyclic compound, 1236000-51-3, name is N-Methyl-1-(4-(trifluoromethoxy)phenyl)methanamine hydrochloride, molecular formula is C9H11ClF3NO, 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.

Intermediate 28 To a solution of 1.0 g of 3-iodobenzoic acid in 20 ml of CH2CI2 under argon atmosphere was added via cannula a solution of 1.11 g of DCC in 22 ml of CH2CI2. The resulting mixture was stirred for 1 h, then was added a solution of 0.65 g of Intermediate 1 and 0.414 ml of Et3N in 13 ml of CH2CI2. The resulting mixture was stirred overnight, diluted with Et2O, filtered off and the filter cake washed with Et2O. The filtrate was washed with 10% NaHCO3 and brine, dried over MgSO4, filtered and concentrated under vacuum. The residue was purified by chromatography on silica gel eluting with EtOAc-Hex 10:90 to 50:50 to afford 1.063 g (91 %) of the title compound as a colourless oil. 1H NMR (delta, ppm, CDCI3): 7.79 and 7.75 (s, 1 H); 7.39 (s, 1 H); 7.23 (d, 2H); 7.21-7.1 1 (m, 2H); 4.72 and 4.49 (s, 2H); 3.02 and 2.88 (s, 3H). [ES MS] m/z: 436 (MH+).

The synthetic route of 1236000-51-3 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; GLAXO GROUP LIMITED; BUENO-CALDERON, Jose Maria; FERNANDEZ-MOLINA, Jorge; LEON-DIAZ, Maria Luisa; MALLO-RUBIO, Araceli; MANZANO-CHINCHON, M Pilar; WO2010/81904; (2010); A1;,
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Adding a certain compound to certain chemical reactions, such as: 172282-50-7, name is 4-(Difluoromethoxy)benzene-1,2-diamine, 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 172282-50-7, SDS of cas: 172282-50-7

Preparation of Intermediate C7. Step 1 . Preparation of C7-1 : To a solution of C4-1 (1 .84 g, 10.93 mmol) and 4-(difluoromethoxy)benzene-1 ,2-diamine (1 .90 g, 10.93 mmol, prepared according to Reference Example 30y of International Patent Publication No. WO 2003/035065, p. 51 1 .) in DMF (40 mL) at rt was added DIPEA (9.5 mL, 54.65 mmol) and HATU (6.23 g, 16.4 mmol). The reaction mixture was stirred at room temperature for 24 h, diluted with ethyl acetate (100 mL), washed with water (100 mL) and brine (50 mL). The mixture was concentrated in vacuo. Purification via silica gel chromatography (EtOAc in hexanes: 20% to 60%) provided C7-1 as the later eluting fraction of two with the similar mass spectra. LCMS-ESr (m/z): [M+H]+ calcd for Ci2H9F4N2O: 289.2; found: 289.0.

At the same time, in my other blogs, there are other synthetic methods of this type of compound, 4-(Difluoromethoxy)benzene-1,2-diamine, and friends who are interested can also refer to it.

Reference:
Patent; GILEAD SCIENCES, INC.; BJORNSON, Kyla; KARKI, Kapil K.; LINK, John O.; PYUN, Hyung-Jung; SCHRIER, Adam J.; STEVENS, Kirk L.; TAYLOR, James G.; VIVIAN, Randall W.; ZABLOCKI, Jeff; ZIPFEL, Sheila; WO2014/145095; (2014); A1;,
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