Ethers-buliding-blocks

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;,
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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;,
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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;,
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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. 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;,
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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. 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;,
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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. 36942-56-0, name is 2-Bromo-4-methoxy-1-methylbenzene, This compound has unique chemical properties. The synthetic route is as follows., Product Details of 36942-56-0

Mg turnings (3 eq., 3.97 g, 163 mmol) were loaded in a two-necked flask, followed by THF (10 ml_) at room temperature. The magnesium was activated by dibromoethane (0.0531 eq., 0.543 g, 0.25 ml_, 2.89 mmol), and then under stirring a solution of 2-bromo-4-methoxy-l-methylbenzene (1 eq., 11 g, 54.5 mmol) in THF (40 ml_) was added dropwise at a rate sufficient to obtain a refluxing solution. After the addition, the light grey solution was stirred for a further 1 h. at 50 C. Then, after cooling to room temperature, the reaction mixture was diluted with THF (50 ml_), and cooled down to 0 C. Then, under vigourous stirring, neat B(OMe)3(3.5 eq ., 19.8 g, 21.6 ml_, 190 mmol) was quickly added in one portion, which caused a white precipitate to appear. After 15 min. of stirring at 0 C, the cooling bath was removed and the reaction mixture was stirred for 1 h. at room temperature. The reaction was then quenched by a 1M HCI solution, and stirred for lh., diluted with Et20, and the phases were separated. The aqueous phase was extracted with an Et20/THF mixture (1 : 1, v/v), and the combined organic phases were dried over Na2S04. The volatile were removed under reduced pressure and the crude off-white solid thus obtained was triturated with /7-pentane under sonication. The crude product is then recrystallized from MeCN (reflux to room temperature to 4-6 C. The titled compound (5-methoxy-2-methylphenyl)boronic acid (7.33 g, 44.2 mmol, 81%) was obtained as a white solid. The title compound as a low solubility in most water-free organic solvents except for THF.400 MHz) : d = 7.07 (d, J = 8.3 Hz, 1H), 7.04 (d, J = 2.8 Hz, 1H), 6.82 (dd, J = 8.3, 2.9 Hz, 1H), 6.14 (s, 2H), 4.87 (s, 2H signal corresponding to the hydrated boronic acid, due the water-contaminated NCCD3), 3.75 (s, 3H), 2.36 (s, 3H) ppm.

According to the analysis of related databases, 36942-56-0, the application of this compound in the production field has become more and more popular.

Reference:
Patent; UNIVERSITE DE STRASBOURG; CENTRE NATIONAL DE LA RECHERCHE SCIENTIFIQUE; DHERBASSY, Quentin; WENCEL-DELORS, Joanna; COLOBERT, Francoise; (46 pag.)WO2019/115597; (2019); A1;,
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Electric Literature of 36805-97-7, 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. 36805-97-7 name is 1,1-Di-tert-butoxy-N,N-dimethylmethanamine, 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.

Compound 2 was prepared according to a similar previously described protocol. 42 To the solution of 4-carboxybenzaldehyde (521?mg, 3.45?mmol) in benzene (6.5?mL) N,N-dimethylformamide di-tert-butyl acetal (2.5?eq, 1760?mg) was added dropwise over a period of 1?h and refluxed. After 2?h the mixture was cooled down to room temperature and water was added (10?mL). The organic layer was collected and concentrated in vacuum. Product was purified chromatographically (silica gel, eluted with Hexane:EtOAc 6:1, v:v). Compound 2 was obtained in 35.4% yield.

At the same time, in my other blogs, there are other synthetic methods of this type of compound, 1,1-Di-tert-butoxy-N,N-dimethylmethanamine, and friends who are interested can also refer to it.

Reference:
Article; Vahter, Juergen; Viht, Kaido; Uri, Asko; Manoharan, Ganesh babu; Enkvist, Erki; Bioorganic and Medicinal Chemistry; vol. 26; 18; (2018); p. 5062 – 5068;,
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Synthetic Route of 20781-20-8,Some common heterocyclic compound, 20781-20-8, name is (2,4-Dimethoxyphenyl)methanamine, molecular formula is C9H13NO2, 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.

Ethyl bromoacetate (Scheme 28) (10.0 gm, 59.87 mmol) solution in 20.0 mL of anhydrous THF was added dropwise to a solution of (2,4-dimethoxybenzyl)amine (10.0gm, 59.81 mmol) and triethyl amine (6.06 gm, 59.87 mmol) in anhydrous THF (20.0 mL) at 0 C under nitrogen atmosphere. The reaction mixture was warmed to room temperature and stirred overnight. Brine was added 100 mL, and the reaction mixture was extracted with ethyl acetate (2 x 100 mL). Combined extracts were dried over anhydrous MgSO4 and concentrated under reduced pressure. The purification wasperformed using combiFlash chromatography, Gradient: 20:80 to 50:50 v/v Ethylacetate:Hexane. 7.6 gm (yield 50.2 %) of the alkylation product was obtained as a colorless liquid. m/z calculated for C13H19N04 [M+H]: 254; Obtained: 254.1. The ester (7.5 gm, 29.6 mmol) was dissolved in 40.0 mL of methanol. The reaction mixture was cooled and 2N aq. NaOH (88.82 mmol, 44.0 mL) solution was addeddropwise. The reaction mixture was warmed to room temperature and stirred for 2 h. The reaction mixture was diluted with 75.0 mL of water, cooled in ice bath and neutralized down to 5.0 to 4.5 pH using 2N aq. HC1. The excess water was concentrated under reduced pressure and air streamed to obtain white solid powder. The solid was dissolved in 85:15 v/v, DCM:MeOH (100.0 mL) and filtered, the filtrate was evaporated to obtain7.1 gm of carboxylic acid as a white powder (Hygroscopic). m/z calculated for C11H15N04 [M+Na]: 248; Obtained: 248.1.j0448J The above compound (7.0 gm, 31.08 mmol) and 6.14 gm, 31.08 mmol of 5- chloroisatoic anhydride were mixed in 70.0 mL of p-Xylene and refluxed at 140 C temperature for 3 h. The reaction mixture filtered and crude product recrystallized frommethanol. 8.5 gm of 7-chloro-4-[(2,4-dimethoxyphenyl)methyl]-2,3,4,5-tetrahydro -1H-1,4-benzodiazepine-2,5-dione was obtained as a white powder (75.8 % yield). m/z calculated for C18H17C1N204 [M+H]: 361; Obtained: 361.1.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route (2,4-Dimethoxyphenyl)methanamine, its application will become more common.

Reference:
Patent; MEKONNEN, Belew; BUTERA, John, A.; HUANG, Jianxing; (400 pag.)WO2016/205739; (2016); A1;,
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Application of 95970-08-4, 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 95970-08-4 as follows.

The product of the third step, 2,5-dibromoanisole 1080 g and DMF 5500 mL, was added to the reaction vessel.Stirring, control temperature was added to 688 g of aluminum trichloride in batches at 80-100 C. The GC tracks until the reaction is over.After the reaction was completed, dichloroethane and water were added, and the mixture was separated.The oil phase was washed with water and separated, and the obtained oil phase was desolvated to obtain a black solid 2,5-dibromophenol 548 g, a content of 98%, and a yield of 53.3%.

According to the analysis of related databases, 95970-08-4, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Changzhou University; Chen Xingquan; Dong Yanmin; (5 pag.)CN109320403; (2019); A;,
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Related Products of 19056-40-7, A common heterocyclic compound, 19056-40-7, name is 4-Bromo-3-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.

To a mixture of 4-bromo-3-methoxyaniline (10 g, 49.5 mmol) and malonic acid (5.15 g, 49.5 mmol) was added POCl3 (5.07 ml, 54.4 mmol) with thorough mixing, and it was then heated to 105¡ãC. After 5 minutes, the reaction began to bubble vigorously, and eventually formed a hard foam and heating was continued for 1 hour. After cooling, water (200 mL) was added, and the mixture was stirred for 30 minutes. The solid was filtered off and washed with water. To the solid was added 2N NaOH (300 mL) and stirring was continued overnight. The remaining solid was filtered off, and EtOH (5 mL) was then added to the filtrate and the basic layer acidified with concentrated HCl to peta 2. The resulting solid was then filtered off, washed with water. The solid was then transferred to a flask and the remaining water was removed by azeotroping with EtOH (200 mL x 2). The solid was then further dried under high vacuum for 15 h to yield 8.75 g of the title compound as an off-white solid. LRMS ESI+ (M+eta)+ Calcd 270.2 Found 272.2.

The synthetic route of 19056-40-7 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; MERCK & CO., INC.; WO2008/57208; (2008); A2;,
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