Month: June 2021

Reference of 399-94-0,Some common heterocyclic compound, 399-94-0, name is 1-Bromo-2,5-difluorobenzene, molecular formula is C6H3BrF2, 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.

Under the protection of nitrogen, 2,5-difluorobromobenzene (15.05g, 78mmol) is dissolved in dry toluene (50 ml), lowering the temperature to ice salt bath -10 C following, dropwise adding isopropyl magnesium chloride/tetrahydrofuran solution of lithium chloride (66 ml, 1.3 mol/L), maintained at about -10 C stirring 1 hour. the1D (10g, 39mmol) dissolved in dry tetrahydrofuran (100 ml) in, is dropped is added to the reaction solution, maintaining the temperature -10 C, canada finishes, to react at room temperature for 4 hours. The temperature dropped to about -10 C, dropwise adding saturated ammonium chloride solution (40 ml), stirring 10 minutes, for 3 mol/L hydrochloric acid solution to adjust pH value to 5 – 6, layered, 3rd phase for methyl tert-butyl ether (50mL × 2) extraction, the combined organic phase, saturated sodium chloride solution (30mL × 2) washing, drying of the organic phase by adding anhydrous sodium sulfate, filtered, concentrated, column chromatography (petroleum ether/ethyl acetate=50:1 – 8:1 (v/v)), get the yellow solid1E(10.1g, 83.5% yield).

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-2,5-difluorobenzene, its application will become more common.

Reference:
Patent; SICHUAN HAISCO PHARMACEUTICAL CO., LTD; ZHANG, CHEN; FAN, JIANG; LI, CAI-HU; WEI, YONG-GANG; (99 pag.)TW2017/8222; (2017); A;,
Bromide – Wikipedia,
bromide – Wiktionary

Related Products of 6274-57-3, These common heterocyclic compound, 6274-57-3, name is 1-(4-Bromophenyl)-N,N-dimethylmethanamine, 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.

Magnesium strips (0.36 g, 15 mmol), a small amount of iodine, 4-bromo-N,N-dimethylbenzylamine (0.21 g, 1 mmol), tetrahydrofuran (25 mL) were added to a round bottom flask, and the mixture was heated to reflux. The reaction is initiated.A solution of 4-bromo-N,N-dimethylbenzylamine (2.98 g, 14 mmol) in THF (5 mL) was then added dropwise over 30 min.After the addition is completed, the reflux is continued for 2 hours.Then cooled to room temperature, and slowly added the compound a derived from amino acid within 30 min.(2-[(tert-Butoxycarbonyl)amino]-3-phenylpropanoic acid methyl ester) (1.40 g, 5 mmol) in THF (5 mL)The saturated ammonium chloride solution was quenched, extracted with ethyl acetate and washed with saturated brine.After drying over anhydrous sodium sulfate, a crude Boc-protected amino alcohol b was obtained, which was used directly in the next step.

The synthetic route of 6274-57-3 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; University of Science and Technology of China; Wang Zhiyong; Gui Yang; (28 pag.)CN108821995; (2018); A;,
Bromide – Wikipedia,
bromide – Wiktionary

Application of 18087-73-5,Some common heterocyclic compound, 18087-73-5, name is 3-Bromoimidazo[1,2-b]pyridazine, molecular formula is C6H4BrN3, 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.

Synthesis of compound 10 (0053) 3-bromoimidazo[1,2-b]pyridazine (compound 9: 10 g, 0.05 mol) was dissolved in acetonitrile (100 ml), under protection of nitrogen, trans-dichlorobis(triphenylphosphine)palladium(II) (1.0 g, 1.4 mmol), cuprous iodide (0.3 g, 1.4 mmol), and dicyclohexylamine (11 ml, 0.06 mol) were added, rise the temperature to 80 C, then trimethylsilyl acetylene (8 ml, 0.6 mol) was added slowly into reaction solution, react for 1 hour, detect with TLC, cool down the reaction solution to room temperature, filter the solution, wash the solid with dichloromethane (200 ml), collect the organic phase, evaporate the solvent, add the residue into dichloromethane (100 ml), wash the organic phase with saturated sodium chloride solution (20 ml x2), dry with anhydrous sodium sulfate, evaporate the solvent for the product. Crystallize the product with ethyl acetate/petroleum ether, to give the black powder solid(compound 10:8.9 g, 81.8% yield). (0054) 1HNMR (CDCl3, 400 MHz) delta: 8.47 (dd, J=1.6, 4.4 Hz, 1H), 7.99(s, 1H), 7.96 (dd, J=1.6, 9.2 Hz, 1H), 7.10 (dd, J=4.4, 9.2 Hz, 1H), 0.33 (s, 9H).

The synthetic route of 18087-73-5 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Chengdu University; ZHENG, Zhebin; (36 pag.)EP3133069; (2017); A1;,
Bromide – Wikipedia,
bromide – Wiktionary

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 5153-40-2 as follows. category: bromides-buliding-blocks

General procedure: A mixture of aryl silane (0.5 mmol), aryl bromides (0.5 mmol), PdCl2(MeCN)2 (5 mol%), and CsF (0.5 mmol) was stirred at 100oC for 6 h in NMP under CO (1atm) (5 mL). Afterwards, 2 mL water was added to the reaction solution and then filtered through a filter paper and the solution was extracted by Et2O (2 mL) for three times. The organic phase was combined and evaporated under reduced pressure. The residue was purified on a SiO2 column to afford the desired product(ethyl acetate/hexane).

According to the analysis of related databases, 5153-40-2, the application of this compound in the production field has become more and more popular.

Reference:
Article; Chang, Sheng; Jin, Ying; Zhang, Xiu Rong; Sun, Yong Bing; Tetrahedron Letters; vol. 57; 19; (2016); p. 2017 – 2020;,
Bromide – Wikipedia,
bromide – Wiktionary

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. 21524-34-5, name is 2-Bromo-1,3,5-triisopropylbenzene, This compound has unique chemical properties. The synthetic route is as follows., Product Details of 21524-34-5

General procedure: Aryl bromide (1mmol), palladium catalyst (1mol%), t-KOBu (1mmol) and DMF (4ml) were added under air to a Schlenck tube containing a stirring bar, followed by (1.5mmol) of phenylacetylene. The reaction mixture was heated to 100C and stirred vigorously for the indicate time then cooled to room temperature. The reaction was quenched with water, and the mixture was extracted with ethyl acetate, dried with MgSO4, and filtered on short silica. Purity of compounds is checked by GC using an internal standard (undecane) and yields are based on aryl bromide

According to the analysis of related databases, 21524-34-5, the application of this compound in the production field has become more and more popular.

Reference:
Article; Dehimat, Zineb Imene; Ya?ar, Sedat; Tebbani, Dahmane; Oezdemir, ?smail; Inorganica Chimica Acta; vol. 469; (2018); p. 325 – 334;,
Bromide – Wikipedia,
bromide – Wiktionary

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. 583-75-5, name is 4-Bromo-2-methylaniline, A new synthetic method of this compound is introduced below., Formula: C7H8BrN

Adding the compound 183a (1.0 g, 5.37 mmol),Compound 183b (2.73 g, 10.75 mmol),Potassium acetate (1.58 g, 16.12 mmol) and PdCl2 (dppf) (0.39 g, 0.54 mmol) were added to 1,4-dioxane (20 mL), replaced with nitrogen three times, and then stirred at 90 C for 4 hours. The reaction solution was cooled to room temperature and filtered.The filter cake was washed with ethyl acetate (15 mL × 2), and the filtrate was concentrated.The concentrate was purified by silica gel chromatography (ethyl acetate: petroleum ether = 0-80%) to obtain a compound 183c as a yellow solid, namely , 2-Dioxoranepentyl-2-yl) aniline (1.21 g, 96.6% yield).

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; Jiaxing Tekeluo Biological Technology Co., Ltd.; Xing Li; Li Guanqun; Wang Xiaolei; Cai Yuting; Jiang Xiang; Pan Xiang; Zhu Wenhao; Wang Yang; Wang Zengquan; (83 pag.)CN110627775; (2019); A;,
Bromide – Wikipedia,
bromide – Wiktionary

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. 68322-84-9, name is 2-Bromo-1-fluoro-4-(trifluoromethyl)benzene belongs to bromides-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below. Quality Control of 2-Bromo-1-fluoro-4-(trifluoromethyl)benzene

3-Bromo-4-fluorobenzotrifluoride (0.38 mL, 2.67 mmol), Cs2C03 (1.74 g, 5.34 mmol), X-Phos (207 mg, 0.036 mmol) and Pd2(dba)3 (164 mg, 0.18 mmol), were added to a mixture of intermediate 31 and intermediate 32 (510 mg, 1.78 mmol) in 2-methyl-2- propanol (40 mL) under a N2 atmosphere. The r.m. was heated at 100 C for 16 h. Then, the r.m. was cooled to r.t., water was added and the r.m. was extracted with DCM. The combined organic layers were dried (MgS04), filtered and concentrated in vacuo. The residue was purified by flash column chromatography (eluent: DCM/MeOH from 100/0 to 95/5). The product fractions were collected and concentrated in vacuo. Both residue was suspended in DIPE and treated with a 6 N HC1 sol. in 2-propanol. Resulting precipitates were collected by filtration. The first compound impure was repurified by RP preparative HPLC [RP Vydac Denali CI 8 – IotaOmicronmu?iota, 250 g, 5cm); mobile phase: a gradient of (0.25% H4HC03 sol. in water/CH3CN)]. The product fractions were collected and concentrated in vacuo. Both residue was crystallized from DIPE, filtered off and dried. Yield: 118 mg of compound 11 (13 %) as HC1 salt (.HC1 .H20) and 97 mg of compound 11a (12 %; regioisomer of compound 11).

The synthetic route of 68322-84-9 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; JANSSEN PHARMACEUTICALS, INC.; BISCHOFF, Francois, Paul; VELTER, Adriana, Ingrid; VAN BRANDT, Sven, Franciscus, Anna; BERTHELOT, Didier, Jean-Claude; WO2012/126984; (2012); A1;,
Bromide – Wikipedia,
bromide – Wiktionary

Related Products of 68322-84-9, 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. 68322-84-9 name is 2-Bromo-1-fluoro-4-(trifluoromethyl)benzene, 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.

To a flask under nitrogen, 3,4-dihydro-2H-benzo[b][1,4]oxazine (Tyger Scientific Inc., Ewing, NJ, 0.457 mL, 3.70 mmol) was dissolved in DMF (18.50 mL) and at room temperature, NaH (60% dispersion in mineral oil) (0.326 g, 8.14 mmol) was added, and the reaction was stirred for 15 minutes. 2-Bromo-1-fluoro-4-(trifluoromethyl)benzene (Alfa Aesar, Ward Hill, MA, 0.790 mL, 5.55 mmol) was then added, and the reaction was stirred overnight at room temperature until complete conversion to the desired product. The reaction was then quenched with saturated aqueous ammonium chloride solution, and extracted with EtOAc (x2). The combined organics were washed with brine, dried over sodium sulfate, and concentrated to give material, which was purified via silica gel MPLC (Biotage Isolera One; PuriFlash HP, 15mu, 25 g (Biotage, Uppsala, Sweden)), eluting with 0 to 100% ethyl acetate in heptanes. Fractions containing clean product were collected and concentrated under a vacuum to yield 1.73 g of 4-(2-bromo-4-(trifluoromethyl)phenyl)-3,4-dihydro-2H-benzo[b][1,4]oxazine (INTERMEDIATE B) as an orange oil. 1H NMR (400 MHz, DMSO-d6) delta ppm 3.62 – 3.69 (m, 2 H) 4.28 (t, J=4.21 Hz, 2 H) 6.30 (dd, J=7.87, 1.71 Hz, 1 H) 6.71 (dtd, J=18.67, 7.42, 7.42, 1.71 Hz, 2 H) 6.85 (dd, J=7.78, 1.81 Hz, 1 H) 7.59 (d, J=8.41 Hz, 1 H) 7.81 (dd, J=8.41, 1.56 Hz, 1 H) 8.13 (d, J=1.66 Hz, 1 H). m/z (ESI) 357.0 (M+H)+

At the same time, in my other blogs, there are other synthetic methods of this type of compound, 2-Bromo-1-fluoro-4-(trifluoromethyl)benzene, and friends who are interested can also refer to it.

Reference:
Patent; AMGEN INC.; BOEZIO, Christiane; BOEZIO, Alessandro; BREGMAN, Howard; CHAKKA, Nagasree; COATS, James R.; COPELAND, Katrina W.; DIMAURO, Erin F.; DINEEN, Thomas; GAO, Hua; LA, Daniel; MARX, Isaac E.; NGUYEN, Hanh Nho; PETERSON, Emily Anne; WEISS, Matthew; WO2013/122897; (2013); A1;,
Bromide – Wikipedia,
bromide – Wiktionary

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. 583-75-5, name is 4-Bromo-2-methylaniline, This compound has unique chemical properties. The synthetic route is as follows., Recommanded Product: 4-Bromo-2-methylaniline

Preparation #4: 2-Methyl-4-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-phenylamine A mixture of 4-bromo-2-methylaniline (0.250 g, 1.34 mmol), bis(pinacolato)diboron (0.442 g, 1.747 mmol), dichloro[1,1’bis(diphenylphosphino)-ferrocene]palladium (II) dichloromethane adduct (0.110 g, 0.134 mmol), and potassium acetate (0.329 g, 3.357 mmol) was heated in N,N-dimethylformamide (5 mL) at about 80 C. for about 15 h under an atmosphere of nitrogen. The mixture was allowed to cool to ambient temperature and was purified by flash column chromatography on silica gel using ethyl acetate/heptane (3:7) as the mobile phase to give 2-methyl-4-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-phenylamine as a yellow oil (0.213 g, 0.914 mmol); RP-HPLC (25% to 100% acetonitrile/0.1 M aqueous ammonium acetate, buffered to pH 4.5, over 10 min at 1.0 mL/min; lambda=254 nm; Hypersil C18, 100 A, 5 mum, 250*4.6 mm column) Rt 11.02 min.

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 583-75-5.

Reference:
Patent; Wishart, Neil; Friedman, Michael; Arnold, Lee D.; Yang, Bryant; Fix-Stenzel, Shannon R.; Ericsson, Anna; Michaelides, Michael R.; Qian, Xiao-Dong; Holms, James H.; Steinman, Douglas H.; Tian, Zhengping; Wittenberger, Steven J.; US2006/25383; (2006); A1;,
Bromide – Wikipedia,
bromide – Wiktionary

Adding a certain compound to certain chemical reactions, such as: 72678-19-4, name is 2,6-Dibromo-4-(trifluoromethyl)aniline, belongs to bromides-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 72678-19-4, Product Details of 72678-19-4

EXAMPLE 4 Synthesis of 2-Amino-4,5-dimethyl-1-(2,6-dibromo-4-trifluoromethylphenyl)pyrrole-3-carbonitrile In 15 ml of toluene, 5.5 g of 4-amino-3,5-dibromobenzotrifluoride, 1.9 g of acetoin, and 34 mg of p-toluenesulfonic acid were dissolved. The reaction solution was heated under reflux for 2.5 hours while conducting azeotropic dehydration. To the reaction mixture, 1.42 g of malononitrile was added. The reaction mixture was heated for 4 hours while being concentrated at 180 C. Water was added to the reaction mixture. The reaction mixture was extracted with chloroform, and subsequently, the extract was dried over anhydrous sodium sulfate. After the desiccant was filtered off, the filtrate was concentrated under reduced pressure. The residue was purified by silica gel column chromatography (eluent:hexane-ethyl acetate=5:1), and was allowed to stand for crystallization to yield 1.2 g of 2-amino-4,5-dimethyl-l-(2,6-dibromo-4-trifluoromethylphenyl)pyrrole-3-carbonitrile. m.p. 158-161 C.

If you are interested in these compounds, you can also browse my other articles.Thank you for taking the time to read this article. I hope you enjoyed it.

Reference:
Patent; Taisho Pharmaceutical Co., Ltd.; US6600038; (2003); B1;,
Bromide – Wikipedia,
bromide – Wiktionary