Month: January 2021

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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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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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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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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Adding a certain compound to certain chemical reactions, such as: 22094-18-4, name is 1,3-Dibromo-2,2-dimethoxypropane, 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 22094-18-4, Safety of 1,3-Dibromo-2,2-dimethoxypropane

To a stirred suspension of NaH (11.7 g, 293 mmol, 60% purity) in DMF (100 ml) was added diisopropylmalonic ester dropwise, keeping the temperature below 40 0C. The resulting mixture was stirred for 1 h at RT and then l,3-dibromo-2,2-dimethoxypropane (34.8 g, 133 mmol) was added in one portion. The resulting mixture was heated at 140 0C for 24 h and then cooled to RT. Saturated NH4Cl aqueous (400 ml) was added and the mixture extracted with hexane (2 x 190 ml). The combined organic phases were washed with H2O (2 x 250 ml) saturated NaHCO3 (2 x 250 ml), H2O (2 x 250 ml) and brine (250 ml). The organic phase was dried (Na2SO4), filtered and concentrated at reduced pressure to provide an orange oil. Purification by in vacuo distillation to remove excess of l,3-dibromo-2,2-dimethoxypropane (b.p. 60-62 0C, 0.1 mniHg) and diisopropylmalonic ester (b.p 78-80 0C, 0.1 mmHg) provided the title compound (20 g, 52%) as orange oil in the distillation flask. MS data: Calculated MH+ (289); Found 100% (MH+) m/z 289.NMR data: 1H NMR (360 MHz, CHLOROFORM- d) delta ppm 5.07 (2 H, spt, J=6.3 Hz), 3.16 (6 H, s), 2.70 (4 H, s), 1.24 (12 H, d, J=6.4 Hz).

In the field of chemistry, the synthetic routes of compounds are constantly being developed and updated. I will also mention this compound in other articles, 1,3-Dibromo-2,2-dimethoxypropane, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; EVOTEC NEUROSCIENCES GMBH; WO2009/135842; (2009); A1;,
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Adding a certain compound to certain chemical reactions, such as: 36942-56-0, name is 2-Bromo-4-methoxy-1-methylbenzene, 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 36942-56-0, Safety of 2-Bromo-4-methoxy-1-methylbenzene

2-bromo-4-methoxytoluene (100 mg, 0.5 mmol),Carbon tetrabromide (16mg, 0.05mmol) was addedInto a reaction flask filled with oxygen,Plug in an oxygen balloon,Finally add 10ml of acetonitrile,Reaction at 400nm LED wavelength and room temperature for 60h,After the reaction, the solvent was distilled off under reduced pressure.Add excess 2mol / L sodium hydroxide solution for washing,Adjust the pH to about 10 ~ 11,The aqueous phase was extracted multiple times with ethyl acetate,Then add 2mol / L of dilute hydrochloric acid to the water phase,Adjust the pH to 1-2,The aqueous phase was extracted again with ethyl acetate several times,Evaporate the ethyl acetate and dry,That gives compound 13,The yield was 78.5%.

In the field of chemistry, the synthetic routes of compounds are constantly being developed and updated. I will also mention this compound in other articles, 2-Bromo-4-methoxy-1-methylbenzene, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; Zhejiang University of Technology; Li Xiaoqing; Zheng Kun; Xu Xiangsheng; (26 pag.)CN110563571; (2019); A;,
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