Month: January 2021

Adding a certain compound to certain chemical reactions, such as: 1535-75-7, name is 2-(Trifluoromethoxy)aniline, 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 1535-75-7, SDS of cas: 1535-75-7

General procedure: To a solution of aldehyde 1 (1 mmol) in methanol, amine 2 (1 mmol), isocyanide 3 (1 mmol), and catalyst pTSIA (20 mol %) were added into a flask. Then the reaction mixture was stirred for 12-24 h at rt (monitored by TLC and LCMS until no further increase in the ratio of the desired product vs starting materials). After completion of reaction the solvent was removed under vacuum to get a crude residue. The crude residue was purified by silica gel column chromatography using (10-30%) ethylacetate-hexane to get the pure product 4.

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

Reference:
Article; Saha, Biswajit; Frett, Brendan; Wang, Yuanxiang; Li, Hong-Yu; Tetrahedron Letters; vol. 54; 19; (2013); p. 2340 – 2343;,
Ether – Wikipedia,
Ether | (C2H5)2O – PubChem

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. 22236-08-4, name is 3-(Difluoromethoxy)aniline, A new synthetic method of this compound is introduced below., Computed Properties of C7H7F2NO

0.429 g of 3-(difluoromethoxy)-aniline (2.7 mmol) were dissolved in 5 mL of pyridine. 1 g of 4-methyl-3-[4-(2,2,2-trifluoro-acetyl)-piperazin-1-yl]-benzenesulfonylchloride (2.7 mmol) were added slowly at room temperature. After stirring for 16 h at room temperature, the reaction mixture was evaporated several times after addition of toluene. The residue was dissolved in dichloromethane and washed several times with 5% aqueous ammonium chloride. The organic phase was then washed with saturated aqueous sodium chloride, dried over sodium sulphate, filtered, and the solvent evaporated. The crude product was purified via silica gel chromatography using dichloromethane/methanol (0-5%) to yield 0.63 g of product.

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; ABBOTT GMBH &; CO. KG; ABBOTT LABORATORIES; HAUPT, Andreas; POHLKI, Frauke; DRESCHER, Karla; WICKE, Karsten; UNGER, Liliane; RELO, Ana-Lucia; BESPALOV, Anton; VOGG, Barbara; BACKFISCH, Gisela; DELZER, Juergen; ZHANG, Min; LAO, Yanbin; WO2010/125134; (2010); A1;,
Ether – Wikipedia,
Ether | (C2H5)2O – PubChem

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. 538-86-3, name is (Methoxymethyl)benzene, A new synthetic method of this compound is introduced below., Recommanded Product: (Methoxymethyl)benzene

General procedure: TsNBr2 (98.7 mg, 0.30 mmol) was added in one portion to a stirred solution of ether (0.20 mmol) andK2CO3 (137.9 mg, 1.0 mmol) in DCM (2.0 mL). The mixture was stirred at 40 ¡ãC for 4 h, and thereaction mixture was cooled to room temperature. Then the reaction was quenched with sat. aqNa2SO3 (2.0 mL) and water (2.0 mL). The mixture was extracted with DCM (3 ¡Á 5.0 mL) and theextracts were combined, washed with brine (10.0 mL), dried over Na2SO4, filtered, and concentratedin vacuo. The residue was purified by flash column chromatography (silica gel, PE-EtOAc) to givethe corresponding product

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; Wang, Yuan-Yuan; Sun, Ming-Hui; Zeng, Ning-Ning; Chen, Jie; Zhou, Ling; Synlett; vol. 27; 9; (2016); p. 1438 – 1442;,
Ether – Wikipedia,
Ether | (C2H5)2O – PubChem

Some common heterocyclic compound, 1516-96-7, name is 5-Bromo-1,3-di-tert-butyl-2-methoxybenzene, molecular formula is C15H23BrO, 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: 5-Bromo-1,3-di-tert-butyl-2-methoxybenzene

Reference Example 3 Bis(3,5-di-tert-butyl-4-methoxyphenyl)phosphine oxide Under argon atmosphere, a solution of magnesium (4.0 g, 0.95 equivalents) and a small amount of iodine in THF (50 mL) was stirred at room temperature for 1 hour. After 4-bromo-2,6-di-tert-butylanisole (52 g, 0.175 mol) synthesised in Reference Example 2 was added at 46C to 53C thereto, the mixture was stirred at 5C for 1 hour. Then, dimethyl phosphite (11.4 g, 0.52 equivalents) was added and the mixture was stirred at 5C for 1 hour. After water (50 mL) was added at 3C and toluene (50 mL) and 6M-HCl (20 mL) were then added, the mixture was stirred at room temperature for 30 minutes. The reaction solution was allowed to separate into layers. An organic layer was washed successively with water (20 mL), a 5% NaHCO3 aqueous solution (20 mL) and a 5% NaCl aqueous solution (20 mL), dried over anhydrous magnesium sulfate and then naturally filtered. The filtrate was concentrated under reduced pressure. The residue was recrystallized from heptane to obtain the title compound (11.6 g, pale yellowish white crystal). Yield 20.5%, mp. 166.1C. 1H-NMR (300 MHz, CDCl3, TMS) delta: 1.38 (s, 36H), 3.68 (s, 6H) 7.49 (s, 2H), 7.54 (s, 2H), 8.01 (d, 1H, J = 474.4 Hz).31P-NMR (121 MHz, CDCl3, 85%H3PO4) delta: 23.57 (dquint, J=474.1 Hz, 14.0 Hz). Elementary analysis for C30H47O3P Calculated value; C: 74.04, H: 9.73, P: 6.36 Found value; C: 74.13, H: 9.93, P: 6.20.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 1516-96-7, its application will become more common.

Reference:
Patent; Takeda Pharmaceutical Company Limited; EP1568701; (2005); A1;,
Ether – Wikipedia,
Ether | (C2H5)2O – PubChem

Synthetic Route of 16618-68-1, 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 16618-68-1 as follows.

4.1.2. Synthesis of 5-hydroxy-7-bromo-quinoline from Scheme 2[0119]The title compound can be purchased by Shanghai Haoyuan Chemexpress Co., Ltd. CHINA or synthesized via known 3-bromo-5-methoxyaniline (Liedholm, Brita. Acta Chemica Scandinavica, Series B: Organic Chemistry and Biochemistry (1984), B38(10), 877-84 or Hodgson, H. H.; Wignall, J. S Journal of the Chemical Society (1926)) in two steps. 3-Bromo-5-methoxy-aniline, 4.6 g (0.05 mol) of glycerol, 2.46 g (0.02 mol) of nitrobenzene and 12 ml of 75% sulfuric acid were stirred for 3 h at 150??? C. After this dark solution was poured onto 100 g of crushed ice, 100 ml of ethylacetate (EtOAc) and 30 ml of 30% solution of NaOH. After 1 hour brown solid was filtered off and the organic layer was separated. After filtering through SiO2 and evaporation of solvent 7-bromo-5-methoxy-quinoline and 5-bromo-7-methoxy-quinoline were separated as mixture approximately 60:40 (total 3.5 g, 74%) This mixture was separated to individual 7-bromo-5-methoxy-quinoline and 5-bromo-7-methoxy-quinoline with column chromatography on silica-gel with benzene-EtOAc (3:1) as eluent. Yield of pure 7-bromo-5-methoxy-quinoline was 950 mg (27% from mixture).

According to the analysis of related databases, 16618-68-1, the application of this compound in the production field has become more and more popular.

Reference:
Patent; BOEHRINGER INGELHEIM INTERNATIONAL GMBH; HOFFMANN, Matthias; BISCHOFF, Daniel; DAHMANN, Georg; KLICIC, Jasna; SCHAENZLE, Gerhard; WOLLIN, Stefan Ludwig Michael; CONVERS-REIGNIER, Serge Gaston; EAST, Stephen Peter; MARLIN, Frederic Jacques; McCARTHY, Clive; SCOTT, John; US2013/29949; (2013); A1;,
Ether – Wikipedia,
Ether | (C2H5)2O – PubChem

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. 115144-40-6, name is 3,4-Difluoroanisole, A new synthetic method of this compound is introduced below., Computed Properties of C7H6F2O

Preparation 4 1-FL UORO-4-METHOXV-2-METHYLSULFANYL-BENZENE 1, 2-Difluoro-4-methoxy-benzene (100mg, 0. 69MMOL) and sodium methanethiolate (148mg, 2. 08MMOL) were dissolved in N, N-DIMETHYLFORMAMIDE (2mL) and the reaction mixture stirred at 60C for 18 hours. Additional sodium methanethiolate (99mg, 139MMOL) was added and the reaction mixture heated to 100C for 18 hours. The reaction mixture was diluted with water and extracted with ether (x 2). The ether extracts were washed with water (x 2), dried over magnesium sulphate and concentrated in vacuo. The residue was taken up in pentane: ether 1: 1 mixture (2mL) and filtered through a plug of silica in a pipette, washing through with pentane: ether 1: 1 mixture (5mL). The reaction mixture was concentrated in vacuo to yield the title product as a colourless oil, 135mg. 1HNMR (CDCI3, 300MHZ) : 2.45 (s, 3H), 3.80 (s, 3H), 6.65 (dd, 1H), 6.80 (dd, 1H), 6.95 (t, 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; PFIZER LIMITED; PFIZER INC.; WO2005/9965; (2005); A1;,
Ether – Wikipedia,
Ether | (C2H5)2O – PubChem

Synthetic Route of 29578-39-0,Some common heterocyclic compound, 29578-39-0, name is 1-Bromo-3-fluoro-5-methoxybenzene, molecular formula is C7H6BrFO, 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.

A RBF was charged with 1-bromo-3-fluoro-5-methoxybenzene (2.104 g, 10.26 mmol), (3-chlorophenyl)boronic acid (1.765 g, 11.29 mmol), potassium carbonate (4.25 g, 30.8 mmol), and Pd(Ph3P)4 (0.593 g, 0.513 mmol). The flask was flushed with Ar (g), then 1,4-dioxane (25.7 ml) and water (8.55 ml) were added. A reflux condenser was attached, and the flask was lowered into a 90 C. heating bath for 45 min. The mixture was cooled to room temperature, diluted with water, and extracted with EtOAc (2*). The combined organic extracts were dried over sodium sulfate, filtered, and concentrated. The residue was purified by chromatography on silica gel (50-g SNAP Ultra column, 25-g silica gel column, 0-5% EtOAc/Heptane) to give 3′-chloro-3-fluoro-5-methoxy-1,1′-biphenyl (2.47 g, 10.44 mmol, 102% yield) as a clear oil containing about 10 wt % impurities.

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-3-fluoro-5-methoxybenzene, its application will become more common.

Reference:
Patent; Amgen Inc.; Weiss, Matthew; Boezio, Alessandro; Boezio, Christiane; Butler, John R.; Chu-Moyer, Margaret Yuhua; Dimauro, Erin F.; Dineen, Thomas; Graceffa, Russell; Guzman-Perez, Angel; Huang, Hongbing; Kreiman, Charles; La, Daniel; Marx, Isaac E.; Milgrim, Benjamin Charles; Nguyen, Hanh Nho; Peterson, Emily; Romero, Karina; Sparling, Brian; US9212182; (2015); B2;,
Ether – Wikipedia,
Ether | (C2H5)2O – PubChem

Synthetic Route of 2398-37-0,Some common heterocyclic compound, 2398-37-0, name is 1-Bromo-3-methoxybenzene, molecular formula is C7H7BrO, 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: A 10 mL vial was charged with CuI (9.5 mg, 0.05 mmol), PSAP (30 mg,0.05 mmol, > 100 mesh), K3PO4 (424 mg, 2 mmol), aryl bromides (1mmol), amines (1.5 mmol), DEG (2 mL), and a magnetic stir bar. The vessel was sealed with a septum and placed into a preheated oil batchat 70 C. The reaction mixture was held at this temperature for 14 hours. After cooling to r.t., the reaction mixture was filtered, and the precipitates were thoroughly washed with water and EtOAc (3 ¡Á 20mL). The combined organic phases were washed with water and brine, dried over anhydrous Na2SO4, and concentrated in vacuo. Theresidue was purified using flash column chromatography on silica gel(eluting with petroleum ether/EtOAc) to afford the desired products.

The synthetic route of 2398-37-0 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Yi, Zhou; Huang, Manna; Wan, Yiqian; Zhu, Xinhai; Synthesis; vol. 50; 19; (2018); p. 3911 – 3920;,
Ether – Wikipedia,
Ether | (C2H5)2O – PubChem

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. 588-63-6, name is (3-Bromopropoxy)benzene, This compound has unique chemical properties. The synthetic route is as follows., name: (3-Bromopropoxy)benzene

Maslinic acid (MA) (150 mg, 0.3 mmol) was dissolved in dry DMF (5 mL), and finely grounded potassium carbonate (200 mg, 1.45 mmol) was added. After 60 min of stirring at 25 ¡ãC, (3-bromopropoxy)-benzene (150 mg, 0.7 mmol) was added, and stirring was continued for another 18 h. The mixture was poured into ice cold hydrochloride acid (5percent, 50 mL), and the white precipitate was filtered off. Chromatographic purification (silica gel, hexane/ethyl acetate, 7:3) followed by recrystallization (ethanol) gave the product; yield: 150 mg, 83percent; m.p. 166?170 ¡ãC; RF = 0.4 (n-hexane/ethyl acetate, 1:1); [alpha]D = +45.8¡ã (c 0.33, CHCl3); IR (KBr): nu = 3424vs, 2946vs, 2930vs, 2878m, 2864m, 1726vs, 1602m, 1498m, 1470s, 1458m, 1384s, 1364m, 1242s, 1202m, 1180m, 1172m, 1162s, 1124m, 1080m, 1052s, 1034m cm?1; 1H NMR (400 MHz, CDCl3): delta = 7.30?7.24 (m, 2H, CHaromat), 6.94 (dd, J = 7.3, 7.3 Hz, 1H, CHaromat), 6.88 (d, J = 8.0 Hz, 2H, CHaromat), 5.25 (dd, J = 3.4, 3.4 Hz, 1H, CH (12)), 4.27?4.14 (m, 2H, CH2 (31)), 4.03 (ddd, J = 6.1, 6.1, 1.5 Hz, 1H, CH2 (33)), 3.68 (ddd, J = 11.5, 9.7, 4.4 Hz, 1H, CH (2)), 2.99 (d, J = 9.5 Hz, 1H, CH (3)), 2.87 (dd, J = 13.8, 3.8 Hz, 1H, CH (18)), 2.18 (brs, 2H, OH), 2.15?2.06 (m, 2H, CH2 (32)), 2.00?1.86 (m, 2H, CHa (16) + CHa (1)), 1.83 (dd, J = 8.8, 3.4 Hz, 2H, CH2 (11)), 1.75?1.66 (ddd, J = 13.8, 13.8, 4.4 Hz, 1H, CHa (7)), 1.67?1.58 (m, 3H, CHa (19) + CHa (15) + CHb (16)), 1.57 (m, 1H, CH (9)), 1.54?1.45 (m, 2H, CHa (22) + CHa (6)), 1.43?1.35 (m, 1H, CHb (7)), 1.33?1.23 (m, 2H, CHa (21) + CHb (6)), 1.22?1.14 (m, 3H, CHb (19) + CHb (21) + CHb (22)), 1.11 (s, 3H, CH3 (27)), 1.02 (s, 3H, CH3 (23)), 1.05?0.95 (m, 1H, CHb (15)), 0.92 (s, 3H, CH3 (25)), 0.90 (s, 3H, CH3 (30)), 0.89 (s, 3H, CH3 (29)), 0.88?0.80 (m, 1H, CHb (1)), 0.81 (s, 3H, CH3 (24)), 0.80 (m, 1H, CH (5)), 0.66 (s, 3H, CH3 (26)) ppm; 13C NMR (100 Hz, CDCl3): delta = 177.8 (C=O, C28), 158.9 (Caromat, C34), 144.0 (C=CH, C13), 129.6 (CHaromat, C35), 122.4 (CH=C, C12), 120.9 (CHaromat, C36), 114.5 (CHaromat, C37), 84.1 (CHOH, C3), 69.1 (CHOH, C2), 64.3 (CH2, C31), 61.1 (CH2, C33), 55.4 (CH, C5), 47.7 (CH, C9), 46.9 (Cquart, C17), 46.5 (CH2, C1), 46.0 (CH2, C19), 41.9 (Cquart, C14), 41.4 (CH, C18), 39.5 (Cquart, C8), 39.3 (Cquart, C4), 38.4 (Cquart, C10), 34.0 (CH2, C21), 33.2 (CH3, C30), 32.7 (CH2, C7), 32.6 (CH2, C22), 30.9 (Cquart, C20), 28.8 (CH2, C32), 28.8 (CH3, C23), 27.7 (CH2, C15), 26.1 (CH3, C27), 23.8 (CH3, C29), 23.6 (CH2, C11), 23.1 (CH2, C16), 18.5 (CH2, C6), 17.1 (CH3, C26), 16.9 (CH3, C24), 16.7 (CH3, C25) ppm; MS (ESI, MeOH, source CID): m/z = 607.3 (20percent, [M + H]+), 629.3 (100percent, [M + Na]+), 929.3 (60percent, [3M + K + H]2+); analysis for C39H58O5 (606.87): C 77.18, H 9.63; found C 77.03, H 9.71.

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 588-63-6.

Reference:
Article; Siewert, Bianka; Csuk, Rene; European Journal of Medicinal Chemistry; vol. 74; (2014); p. 1 – 6;,
Ether – Wikipedia,
Ether | (C2H5)2O – PubChem

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. 107622-80-0, name is (4-Phenoxyphenyl)methanamine, A new synthetic method of this compound is introduced below., Safety of (4-Phenoxyphenyl)methanamine

EXAMPLE 4 N-isoquinolin-5-yl-N’-(4-phenoxybenzyl)urea The title compound was prepared using 4-phenoxybenzylamine, DBU, the product from Example 1A and the procedure described in Example 1B. 1H NMR(300MHz, d6-DMSO) delta 9.30 (s, 1H), 8.75 (s, 1H), 8.58 (d, 1H), 8.31 (d, 1H), 7.92 (d, 1H), 7.75 (d, 1H), 7.60 (t, 1H), 7.40 (m, 4H), 7.18-6.95 (m, 6H), 4.38 (d, 2H); MS (DCI/NH3) m/z 369 (M+H)+.

The synthetic route of 107622-80-0 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Lee, Chih-Hung; Bayburt, Erol K.; DiDomenico JR., Stanley; Drizin, Irene; Gomtsyan, Arthur R.; Koenig, John R.; Perner, Richard J.; Schmidt JR., Robert G.; Turner, Sean C.; White, Tammie K.; Zheng, Guo Zhu; US2003/158188; (2003); A1;,
Ether – Wikipedia,
Ether | (C2H5)2O – PubChem