Tag: M.W=200-300

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. 450-88-4, name is 1-Bromo-4-fluoro-2-methoxybenzene, A new synthetic method of this compound is introduced below., Recommanded Product: 450-88-4

Step B: 4-fluoro-2-methoxybenzonitrile: To a solution of 1-bromo-4-fluoro-2-methoxybenzene(25 g, 0.12 mol) in 250 mL ofDMF was added Zn(CN)2 (28.6 g, 0.240 mol) and Pd(PPh3)4 (7.05g, 6.10 mmol) at one portion and the reaction was charged with Ar and heated to 100 C for 10 hours. Then the reaction was poured into IL ofEtOAc and filtered through a kieselguhr pad.The filtrate was washed with water, brine, dried and concentrated to solid, which was purified bysilica gel column to give 4-fluoro-2-methoxybenzonitrile.

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; MERCK SHARP & DOHME CORP.; PASTERNAK, Alexander; BLIZZARD, Timothy; CHOBANIAN, Harry; DE JESUS, Reynalda; DING, Fa-Xiang; DONG, Shuzhi; GUDE, Candido; KIM, Dooseop; TANG, Haifeng; WALSH, Shawn; PIO, Barbara; JIANG, Jinlong; WO2013/28474; (2013); A1;,
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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. 19056-41-8, name is 3-Bromo-4-methoxyaniline belongs to ethers-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below. name: 3-Bromo-4-methoxyaniline

Example 31 STR39 2-Bromo-1-methoxy-4-pentafluorophenylsulfonamidobenzene. 1 H NMR (CDCl3): 7.35(d, J=3 Hz, 1H), 7.15(dd, J=9 Hz, 3 Hz, 1H), 6.97 (s, 1H), 6.81(d, J=9 Hz, 1H), 3,88 ppm (s, 3H). EI m/z: 433(35, M+), 202(100). The compound was prepared by a protocol similar to that of example 1 by replacing N,N-dimethyl-1,4-phenyldiamine dihydrochloride with 3-bromo-4-methoxyaniline.

The synthetic route of 19056-41-8 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Tularik Inc.; US5880151; (1999); A;,
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Electric Literature of 588-63-6,Some common heterocyclic compound, 588-63-6, name is (3-Bromopropoxy)benzene, molecular formula is C9H11BrO, 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 suspension of the phenoxypropyl bromide (44) (0.3 mL, 1.90 mmol, d=1.365), piperidone hydrochloride hydrate (0.44 g, 2.86 mmol), K2CO3 (1.05 g, 7.62 mmol), anhydrous Na2SO4 (0.54 g, 3.81 mmol) and KI (47 mg, 0.286 mmol) in MeCN (20 mL) was stirred at reflux conditions for 2.5 hrs. The mixture was cooled to RT, diluted with water and extracted with EA. The extract was dried over Na2SO4, filtered, concentrated and the residue was purified by flash column chromatography, eluent 5percent MeOH in EA, to afford title compound 45 (0.45 g, quant. yield) as oil. (0383) 1H NMR: 500 MHz, CDCl3, delta (ppm): 7.30-7.26 (m, 2H), 6.96-6.90 (m 3H), 4.06 (t, J=6.3 Hz, 2H), 2.78 (t, J=6.1 Hz, 4H), 2.66 (t, J=7.1 Hz, 2H), 2.46 (t, J=6.8 Hz, 4H), 2.04-1.99 (m, 2H). MS: 233.3 (calcd.), 234.1 (M+H+, found).

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

Reference:
Patent; Mirati Therapeutics, Inc.; Marx, Matthew Arnold; Vaisburg, Arkadii; Christensen, James Gail; Galemmo, JR., Robert Anthony; (91 pag.)US2017/183308; (2017); A1;,
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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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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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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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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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These common heterocyclic compound, 64115-88-4, name is 1-Bromo-2-(trifluoromethoxy)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. Safety of 1-Bromo-2-(trifluoromethoxy)benzene

2.0 g of 1-bromo-2-(trifluoro-methoxy)benzene (8.3 mmol) were dissolved in 30 ml of dichloromethane. At 0-50C, 1.06 g of chlorosulfonic acid (9.13 mmol), dis? solved in 3 ml of dichloromethane, were added dropwise. The reaction mixture was stirred for 30 min at room temperature. Additional 5.5 equivalents of chloro- sulfonic in dichloromethane were added to drive the reaction to completion.Standard work-up was followed and silica gel chromatography with n-heptane- dichloromethane (6:4) as eluent gave 2.19 g of the title compound.1H-NMR (CDCl3, 400 MHz): delta [ppm] 8.3 (d, 1H), 8.05 (dd, 1H), 7.5 (dd, 1H).

The synthetic route of 1-Bromo-2-(trifluoromethoxy)benzene has been constantly updated, and we look forward to future research findings.

Reference:
Patent; ABBOTT GMBH & CO. KG; WO2006/40179; (2006); A1;,
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Application of 5414-19-7, 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. 5414-19-7, name is 1-Bromo-2-(2-bromoethoxy)ethane belongs to ethers-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below.

To a stirred solution of 3-amino-1-bromoisoquinoline (444 mg, 2.00 mmol) in anhydrous dimethylformamide (10 mL) was added sodium hydride (60%, unwashed, 96 mg, 2.4 mmol) in one portion. The mixture was stirred at 25 C. for 5 min before 2-bromoethyl ether (90%, 250 muL, 2.00 mmol) was added. This mixture was stirred further at 25 C. for 5 h and at 75 C. for 72 h before it was cooled to 25 C., quenched with saturated ammonium chloride solution and diluted with ethyl acetate. The organic layer was separated, washed with water and brine, dried over Na2SO4, filtered and concentrated. Purification of the residue on silica gel (gradient elution with 0% to 70% ethyl acetate in hexanes) afforded Cap-143, step a (180 mg, 31%) as a yellow solid. Rt=1.75 min (Cond.-MS-W1); 90% homogenity index; LCMS: Anal. Calc. for [M+H]+ C13H14BrN2O: 293.03; found: 293.04.

The synthetic route of 1-Bromo-2-(2-bromoethoxy)ethane has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Bristol-Myers Squibb Company; US2010/249190; (2010); A1;,
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Reference of 36449-75-9, These common heterocyclic compound, 36449-75-9, name is 1-(2-Bromoethyl)-2-methoxybenzene, 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: General synthetic procedure for the final products.The appropriately substituted 4-phenethylpiperidine (6)(0.5 mmol) was dissolved in acetonitrile (5 mL) and K2CO3(0.75 mmol) and the appropriate phenethyl bromide (7) (0.5 mmol) added. The reaction mixture was refluxedfor 8 h.After completion of the reaction (monitored by TLC), the reaction mixture was cooled to ambient temperature and filtered through a Celite pad. The filtrate was concentrated under vacuum to obtain the desired crude product. The crude product was further purified by column chromatography (silica gel: 3-5% methanol in dichloromethane) to afford the corresponding 1,4-diphenethylpiperidine (8a-8y) in good yield (75-80 %), which was then converted to hydrochloride salt by treatment with 2M HCl in diethyl ether.Compounds12a-12dwere synthesized using the same procedure as above, except that an appropriately substituted 4-benzylpiperidine (11) was utilized in place of compound6.

The synthetic route of 36449-75-9 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Nickell, Justin R.; Culver, John P.; Janganati, Venumadhav; Zheng, Guangrong; Dwoskin, Linda P.; Crooks, Peter A.; Bioorganic and Medicinal Chemistry Letters; vol. 26; 13; (2016); p. 2997 – 3000;,
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