Ethers-buliding-blocks

These common heterocyclic compound, 538-86-3, name is (Methoxymethyl)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. Quality Control of (Methoxymethyl)benzene

Commercially available from Sigma-Aldrich is benzyl methyl ether, PhCH2OCH3. To 100 ml of diethyl ether in a Parr pressure vessel, 3.62 g (0.032 moles) of potassium t-butoxide is added with stirring. To this suspension 2 ml (0.016 moles) of benzyl methyl ether is slowly added. Oxygen is removed from the flask by alternating cycles (10) of inert gas pressurization and venting. The stirred solution is then exposed to 80 psi NO gas at room temperature for 24 hours. When the reaction is complete, i.e. no more NO gas was consumed, then the head space is purged of NO gas and the tan solid filtered and washed with ether. The UV-vis spectrum of this material has a peak at 258 nm and it yields a positive Greiss reaction. The crude tan product is analyzed for NO release. A solution is made of 6.7 mg of the tan product in 0.1 ml of 10 mM NaOH. In a reactor vessel containing 3 ml of pH 7.4 buffer is injected the 0.1 ml of the tan product solution. The tan product generates 0.13 mg of NO over a 79 minute time period.

The synthetic route of (Methoxymethyl)benzene has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Arnold, Ernst V.; Doletski, Blaine G.; Raulli, Robert E.; US2005/203069; (2005); A1;,
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20469-65-2, name is 1-Bromo-3,5-dimethoxybenzene, 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. SDS of cas: 20469-65-2

To a mixture of 1-bromo-3,5-dimethoxybenzene (15 g, 69.1 mmol) in dichloromethane (500 ml) at 0 C. was added BBr3 (14.37 ml, 152 mmol) dropwise over 5 minutes at 0 C. The reaction mixture was allowed to warm to room temperature and stirred for 5 hours. The reaction was then cooled to 0 C. and BBr3 (7.2 ml, 76 mmol) added dropwise. The reaction mixture was allowed to warm up to room temperature and stirred overnight. The reaction was again cooled to 0 C. and BBr3 (3.6 ml, 38 mmol) added dropwise. The reaction mixture was allowed to warm up to room temperature and stirred for 4 hours. The mixture was then poured slowly onto ice. When the ice melted, DCM (200 ml) was added and the layers separated. The aqueous was extracted with EtOAc (500 ml) and the layers separated. The combined organics were passed through a through a hydrophobic frit and concentrated. The residue was purified via flash chromatography (ISCO Combiflash Rf, 220 g column, 0-100% ethyl acetate/hexanes) to give the title compound as a yellow oil (19.5 g, 70% purity). MS (m/z) 189.0 (M+).

The synthetic route of 20469-65-2 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; GLAXOSMITHKLINE INTELLECTUAL PROPERTY (NO.2) LIMITED; DOWDELL, Sarah E.; EIDAM, Hilary Schenck; ELBAN, Mark; FOX, Ryan Michael; HAMMOND, Marlys; HILFIKER, Mark A.; HOANG, Tram H.; KALLANDER, Lara; LAWHORN, Brian Griffin; MANNS, Sharada; PHILP, Joanne; WASHBURN, David G.; YE, Guosen; (190 pag.)US2016/340328; (2016); A1;,
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Some common heterocyclic compound, 944317-92-4, name is 1-Bromo-4-fluoro-5-isopropyl-2-methoxybenzene, molecular formula is C10H12BrFO, 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. Recommanded Product: 944317-92-4

General procedure: A 500 mL dry flask was charged with 1-bromo-4-fluoro-5-isopropyl-2-methoxybenzene (BrMIP) (24.60 g, 0.10 mol) and dissolved in toluene (80 mL) and THF (80 mL). The resulting solution was flushed with argon, and tri- isopropylborate (32 mL, 0.1 mol) was added. The mixture was cooled to -80 C. Then 2.5 n-BuLi in hexanes (48 mL, 0.12 mol) was added slowly, maintaining a temperature below -55C. After completion of the n-BuLi addition, the reaction mixture was slowly warmed (1 hour) to -10C and water (120 mL) was added, followed by commercially available 2-bromo-5-(trifluoromethyl)benzonitrile (Formula VI’, X = Br, R2 = CN) (25.00 g, 0.10 mmol) and the catalyst, 1 , 1 bis( di-tertbutylphosphino)ferrocene palladium dichloride (265 mg, 0.8 mol%) addition. The organic layer turns dark brown immediately. The biphasic mixture is aged at room temperature with vigorous stirring for 12 hours. The aqueous layer was removed and the organic layer was washed with 1 M NaOH (aq) (100 mL), water (300 mL) and filtered through silica gel. The solvent was removed under reduced pressure to yield brown oil which was crystallized from EtOH/water (300/100 mL). The resulting slurry was filtered and the filter cake was washed with cold 50% EtOH. The product was dried at 40 C under vacuum to yield 4′-fluoro-5′- isopropyl-2′-methoxy-4-(trifluoromethyl)biphenyl-2-carbonitrile (Formula VII’, Ri = CN, R2 = isopropyl) as a pale white solid (25.20 g, 75%). According to the same procedure in various scales and different concentrations of catalyst some other biaryl of Formula Vlh and Vll2 are prepared and listed in Table 3 and Table 4, respectively. For NMR data and melting points see Table 1 and 2.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 944317-92-4, its application will become more common.

Reference:
Patent; LEK PHARMACEUTICALS D.D.; HUMLJAN, Jan; MARAS, Nenad; WO2013/91696; (2013); A1;,
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Application of 16452-01-0, A common heterocyclic compound, 16452-01-0, name is 3-Methoxy-4-methylaniline, molecular formula is C8H11NO, 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.

Reference Production Example 79 (1473) A mixture of 6.85 g of 3-methoxy-4-methylaniline and 150 mL of chloroform was cooled to 0 C. and 26.5 g of tetrabutylammonium tribromide was added, followed by stirring at the same temperature for 20 minutes. To the reaction mixture, chloroform was added. The organic layer was washed with a sodium bicarbonate solution, an aqueous sodium sulfite solution, water, and a saturated saline solution, dried over anhydrous sodium sulfate, and then concentrated under reduced pressure. (1474) The residue thus obtained was subjected to silica gel column chromatography to obtain 7.85 g of 2-bromo-5-methoxy-3-methylalanine. (1475) 1H-NMR (CDCl3) delta: 2.08 (3H, s), 3.76 (3H, s), 3.93 (2H, br s), 6.28 (1H, s), 7.12 (1H, s).

The synthetic route of 16452-01-0 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; SUMITOMO CHEMICAL COMPANY, LIMITED; AZUMA, Shuhei; ARIMORI, Sadayuki; MAEHATA, Nao; (235 pag.)US2016/150787; (2016); A1;,
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Adding a certain compound to certain chemical reactions, such as: 5414-19-7, name is 1-Bromo-2-(2-bromoethoxy)ethane, 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 5414-19-7, SDS of cas: 5414-19-7

General procedure: 1,3-Dibromopropane (2.2 Kg, 10.9 mol) was slowly added to a stirred suspension of 264 g magnesium turnings (11 mol)In tetrahydrofuran (17.6 L).Control the dropping rate to maintain the reaction temperature at minus 40 ~ 50 degrees Celsius.After the addition is complete, the mixture is precooled to minus 50 degrees Celsius for two hours at minus 40 to 50 degrees Celsius,And the reaction mixture prepared from 2-chloropyridine was added.Control the dropping rate to maintain the reaction temperature at minus 40 ~ 50 degrees Celsius.After the addition was completed, the temperature was slowly raised to 60 C and stirred for 3 hours.The reaction mixture was concentrated under reduced pressure to 20 liters of n-hexane (20 L).The resulting solid was removed by filtration.Concentration of the filtrate followed by pressure distillation gave the desired target intermediate (1.16 Kg, 62%) as a colorless liquid.

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Reference:
Patent; Zhejiang Xingyue Pharmaceutical Technology Co., Ltd.; Ying Lv; Chen Qingquan; Hu Junbin; (103 pag.)CN104177394; (2017); B;,
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Synthetic Route of 6358-77-6, A common heterocyclic compound, 6358-77-6, name is 5-Bromo-2-methoxyaniline, molecular formula is C7H8BrNO, 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: Preparation of (±)-12: A pressure glass tube charged with trifluoroborate (±)-10 (31 mg, 0.10 mmol), Cs2CO3 (98 mg, 0.30 mmol) and PdCl2(dppf)·CH2Cl2 (4 mg, 5 mol %) was alternatively evacuated and sparged with argon three times. A solution of 4-bromoanisol (21 mg, 0.11 mol) in toluene (1.5 mL) previously flushed with argon, then water (0.5 mL) were added by syringes. The reaction mixture was stirred at 100 C for 18 h and then cooled to room temperature. Water (5 mL) was added and the mixture extracted with EtOAc (5 mL × 2). The combined organic layers were washed with water (5 mL × 2), dried (MgSO4) and concentrated in vacuo. The residue was purified by column chromatography (cyclohexane/EtOAc 9:1), affording 12 as a colorless oil (24 mg, 75%).

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; Ty, Nancy; Pontikis, Renee; Chabot, Guy G.; Devillers, Emmanuelle; Quentin, Lionel; Bourg, Stephane; Florent, Jean-Claude; Bioorganic and Medicinal Chemistry; vol. 21; 5; (2013); p. 1357 – 1366;,
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These common heterocyclic compound, 14227-17-9, name is 2,4,6-Trimethoxyaniline, 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. HPLC of Formula: C9H13NO3

Intermediate 4 (100 mg) was added to 3 MI of POCl3 at 0 C. 2,4, 6- TNMETHOXYBENZENAMINE (0.13 g) was added and the reaction mixture was stirred for 3 to 5 days. The ice bath was allowed to melt during the first couple of hours. After that, the POC13 suspension was dropped to 200 ml of vigorously stirred diisopropyl ether. The solid material was filtered off and washed with diisopropyl ether. The residue was immediately stirred in ETOAC/SATURATED aqueous NAHCO3 (1/1) (200 ML) for 1 hour. The EtOAc was dried using brine and NA2SO4 successively and evaporated. The residue was purified by preparative TLC using CH2CI2/MEOH (95/5) as the eluent or by precipitation in CH2CLZ/MEOH. Yield: 0.01 g of compound 36 (8%).

The synthetic route of 2,4,6-Trimethoxyaniline has been constantly updated, and we look forward to future research findings.

Reference:
Patent; JANSSEN PHARMACEUTICA N.V.; ARTS, Theodora, Joanna, Francisca; JANSSEN, Graziella, Maria, Constantina; JANSSEN, Herwig, Josephus, Margareta; JANSSEN, Jasmine, Josee, Werner; JANSSEN, Paul, Peter, Maria; JANSSEN, Maroussia, Godelieve, Frank; WO2004/74266; (2004); A1;,
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Reference of 1535-75-7, These common heterocyclic compound, 1535-75-7, name is 2-(Trifluoromethoxy)aniline, 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: Acetamides (1a-1x, 1ab, 1ac and 1ba-1bc). To a solution of 2-phenylacetic acid (7.0mmol), 2-(trifluoromethoxy)aniline (7.7mmol) in anhydrous CH2Cl2 (25mL) were added EDCI (1.745g, 9.1mmol) and DMAP (256.6mg, 2.1mmol). The reaction mixture was stirred at room temperature overnight, diluted with HCl (1M) aqueous solution, and extracted with CH2Cl2 (3×25mL). The combined organic phase was washed with saturated NaHCO3 aqueous solution and brine, dried over anhydrous Na2SO4, and concentrated under vacuum. Purification by flash chromatography (Silica gel, petroleum ether: ethyl acetate=50: 1 as eluent) gave the corresponding 2-phenyl-N-[2-(trifluoromethoxy)phenyl]acetamide compound.

The synthetic route of 1535-75-7 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Zhao, Xiao-Jing; Zhao, Jie; Sun, Xin; Liu, Ji-Kai; Wu, Bin; Tetrahedron; vol. 73; 25; (2017); p. 3463 – 3477;,
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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. 4316-51-2, name is 4-Methoxytriphenylamine, This compound has unique chemical properties. The synthetic route is as follows., Formula: C19H17NO

POCl3 (6 mL, 64.17 mmol) was carefully added to a solution of 4-methoxy-N,N-diphenylaniline (10 g, 36.32 mmol), DMF (5 mL, 64.85 mmol) and 50 mL of 1,2-dichloroethane. The mixture was refluxed for 4 h, then cooled to room temperature (r.t.), and poured into a saturated aqueous sodium acetate solution (100 mL). The product was extracted with dichloromethane. The organic layer was dried over anhydrous MgSO4. The solvent was evaporated by a rotary evaporator. The residue was purified by silica gel column chromatography using ethyl acetate: n-hexane (2:3) to give (1) (7.6 g, Yield: 69%). TOF/MS (ESI): found 326.1 (M+Na+). 1H NMR (300 MHz, CDCl3, delta): 9.79 (s, 1H, ArCHO), 7.68-6.89 (m, 14H, ArH), 3.83 (s, 3H, ArOCH3).

According to the analysis of related databases, 4316-51-2, the application of this compound in the production field has become more and more popular.

Reference:
Article; Giang, Ha Ngoc; Kinashi, Kenji; Sakai, Wataru; Tsutsumi, Naoto; Journal of Photochemistry and Photobiology A: Chemistry; vol. 291; (2014); p. 26 – 33;,
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Application of 929-75-9,Some common heterocyclic compound, 929-75-9, name is 1,11-Diamino-3,6,9-trioxaundecane, molecular formula is C8H20N2O3, 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: 0.41 mmol of polyethylene glycol diamine,DIPEA105 mg, 4-fluoro-2- (2,6-dioxopiperidin-3-yl) ethindol-1,3-one,Add DMF 2mL, 90 C for 12 h. Cool to room temperature,Add water 20mL, ethyl acetate extraction,The extract is saturated with saline,Dried over anhydrous magnesium sulfate,Evaporated under reduced pressure,Silica gel column chromatography (methanol: dichloromethane 1; 10)Intermediate 7.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 1,11-Diamino-3,6,9-trioxaundecane, its application will become more common.

Reference:
Patent; Jilin University; Lu Haibin; Wang Shihui; Li Haiyan; Wang Chunhe; Deng Jiayu; Feng Mingming; Guo Yu; Su Runping; Jin Xiangqun; (26 pag.)CN106543185; (2017); A;,
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