Bromides-buliding-blocks

Related Products of 937046-98-5, 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. 937046-98-5 name is 7-Bromopyrrolo[2,1-f][1,2,4]triazin-4-amine, 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 solution of 7-bromopyrrolo[2,l- f][l,2,4]triazin-4-amine (2 g, 9.39 mmol, 2.98 equiv) in anhydrous THF (200mL) under inert atmosphere, was added 1,1 ,4,4-tetramethyl- 1 ,4-dichlorodisilyethylene(2. 2 g, 9.46 mmol, 1.1 equiv) along with sodium hydride (754 mg, 18.92 mmol, 2.2 equiv) and the mixture was stirred for 20 mm at room temperature. The reaction was then cooled to -78C before nbutyllithium (11.4 mL, 28.38 mmol, 2.5 M in hexanes) was added slowly over 10 mm. The reaction was allowed to stir for a further 15 mm before (3R,4 R, 5R)-3,4-bis(benzyloxy)-5- [(benzyloxy)methyl]oxolan-2-one (3.6 g, 8.60 mmol, 1.00 equiv) (dissolved in 5 mL THF) was added dropwise. The resulting solution was stirred for 1 h at -78 C, then quenched by the addition of 200 mL sat. ammonium chloride (aq.). The resulting solution was extracted with of ethyl acetate (200 mL x 3) and the organic layers combined, dried over sodium sulfate and concentrated under reduced pressure. The crude product was purified by reverse phase flash chromatography (ACN/H20). This resulted in 2 g (42%) of the title compound as a yellow solid. MS m/z [M+H] (ESI):553.

At the same time, in my other blogs, there are other synthetic methods of this type of compound, 7-Bromopyrrolo[2,1-f][1,2,4]triazin-4-amine, and friends who are interested can also refer to it.

Reference:
Patent; ALIOS BIOPHARMA, INC.; BEIGELMAN, Leonid; DEVAL, Jerome; PRHAVC, Marija; (145 pag.)WO2019/53696; (2019); A1;,
Bromide – Wikipedia,
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Adding a certain compound to certain chemical reactions, such as: 65896-11-9, name is 2-Bromo-6-fluoroaniline, 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 65896-11-9, SDS of cas: 65896-11-9

General procedure: D.7. Synthesis of com ounds 126 to 131. 126 to 131 To a solution of anilines (0.12 mmol) in THF (800 mu) at 0 C, was added triphosgene (21 mg, 0.07 mmol). The mixture is stirred at rt for 1 h30, then TEA (70 mu, 0.50 mmol), (1 S)-1-methyl-1 ,2,3,4-tetrahydroisoquinoline hydrobromide (commercial, 27 mg, 0.12 mmol). The mixture was stirred at rt for 1 h, then overnight at 60 C. The reaction mixture is diluted with EtOAc (2 mL), then washed with an aqueous saturated solution of NaHC03. The organic layer was dried over MgS04, filtered and concentrated under vacuum. The residue was purified by reverse phase chromatography (basic mode, LCMS prep). compounds 126, 127, 128, 129, 130 and 131 were synthesized following this method. (1 S)-N-(2-bromo-6-fluorophenyl)-1-methyl-3,4-dihvdroisoguinoline-2(1 H)-carboxamide 126. Compound 126 was prepared using 2-bromo-6-fluoroaniline as starting material Yield: 52%. LCMS (ES+): 363 (M+H)+, 96.9% purity.

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; UCB BIOPHARMA SPRL; VALADE, Anne; JNOFF, Eric; ATES, Ali; BURSSENS, Pierre; SKOLC, David; (211 pag.)WO2016/55479; (2016); A1;,
Bromide – Wikipedia,
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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 2635-13-4 as follows. Application In Synthesis of 5-Bromobenzo[d][1,3]dioxole

General procedure: A 10-mL vial was charged with aryl halide (0.5 mmol), Cs2CO3 (1 mmol), Cu2O (0.05 mmol), N-containing heterocycles (0.75 mmol), DMF (1 mL), and a magnetic stir bar. The mixture was stirred at 120 C (130 C for entry 19). The reaction mixture was held at this temperature for 12 h (24 h for entry 18, 20, 21, and 25). After allowing the mixture to cool to room temperature, the reaction mixture was extracted with ethyl acetate (3 10 mL), dried over anhydrous Na2SO4, and concentrated in vacuo. The residue was purified by silica gel chromatography (ethyl acetate/petroleum ether as the eluent) to provide the target products 3a-3t.

According to the analysis of related databases, 2635-13-4, the application of this compound in the production field has become more and more popular.

Reference:
Article; Wang, Xiaochuang; Wang, Meiji; Xie, Jianwei; Synthetic Communications; vol. 47; 19; (2017); p. 1797 – 1803;,
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. 1435-53-6, name is 2,4-Dibromo-1-fluorobenzene, A new synthetic method of this compound is introduced below., Computed Properties of C6H3Br2F

General procedure: To a mixture of 1,3-dibromo-5-fluorobenzene (1.39 g, 5.51 mM), 2-tri-n-butylstannylpyridine(5.00 g, 13.6 mM), bis(triphenylphosphine)palladium dichloride (1.00 g, 1.43 mM),and lithium chloride (0.37 g, 8.84 mM) in an oven dried Schlenk tube, distilled toluene(40 mL) was added. The mixture was degassed via the freeze-pump-thaw method until nogas bubbles were observed and refluxed at 110 C under nitrogen for 48 h. After coolingthe reaction mixture to room temperature, an aqueous solution of potassium fluoride(40 mL) was added and the insoluble black residue was filtered and washed with toluene.The toluene was removed under reduced pressure. Dichloromethane (100 mL) and aqueoussodium bicarbonate (100 mL) were added to the remaining residue. The organic phase wasseparated, washed with sodium bicarbonate (2 ¡Á 100 mL), then dried over anhydroussodium sulfate and evaporated to obtain a yellow residue. This residue was then purifiedover silica with a mixture of 90% hexane: 10% diethyl ether, whose mole fraction was measuredto 50% hexane: 50% diethyl ether to obtain a pale yellow solid (0.8078 g, 58%).

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; Papo, Tshephiso R.; Jaganyi, Deogratius; Journal of Coordination Chemistry; vol. 68; 5; (2015); p. 794 – 807;,
Bromide – Wikipedia,
bromide – Wiktionary

Adding a certain compound to certain chemical reactions, such as: 7745-91-7, name is 3-Bromo-4-methylaniline, 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 7745-91-7, Recommanded Product: 7745-91-7

Methyl chloroformate (0.202 ml, 2.62 mmol) was added to a solution of 3-bromo-4-methyl-phenylamine (243 mg, 1.31 mmol) in pyridine (2 ml), and the mixture was stirred at room temperature overnight. H2O was added to the reaction mixture, followed by extraction with AcOEt (x 2). The organic layers were combined and sequentially washed with H2O and saturated brine, and then dried over Na2SO4 and concentrated under reduced pressure. The resulting residue was purified by silica gel chromatography (n-hexane/AcOEt) to give (3-bromo-4-methyl-phenyl)-carbamic acid methyl ester (288 mg, 90%). 1H-NMR (270 MHz, CDCl3) delta 2.34 (3H, s), 3.77 (3H, s), 6.51 (1H, br. s), 7.14 (1H, d, J = 7.2 Hz), 7.20 (1H, dd, J = 7.4, 2.0 Hz), 7.63 (1H, d, J = 2.0 Hz).

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; Chugai Seiyaku Kabushiki Kaisha; EP2433940; (2012); A1;,
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Electric Literature of 74586-53-1, The chemical industry reduces the impact on the environment during synthesis 74586-53-1, name is 3-Bromo-5-methylaniline, I believe this compound will play a more active role in future production and life.

INTERMEDIATE 8: N-[3-methyl-5-(4,4,5,5-tetramethyl- 1 ,3,2-dioxaborolan-2-yl)phenyl]-4- (trifluoromethyl)pyrimidin-2-amineStep 1 : A solution of 3-bromo-5-methylaniline (162.5 g, 873.66 mmol) in 1,4-dioxane (2 L) was prepared, and 2-chloro-4-(trifluoromethyl)pyrimidine (182 g, 994.54 mmol) and methanesulfonic acid (97.5 g, 1.02 mol) were added sequentially. The resulting solution was heated to reflux overnight. The resulting mixture was cooled and concentrated in vacuo. The residue was diluted with 2 L of water, then adjusted to pH 7-8 with aqueous saturated sodium bicarbonate solution, followed by extraction with EtOAc (2×2 L). The organic layers were combined, washed with water (2x 2 L), dried over anhydrous sodium sulfate and concentrated in vacuo to afford N-(3- bromo-5-methylphenyl)-4-(trifluoromethyl)pyrimidin-2-amine as a light yellow solid. MS ESI calc’d for Ci2H,oBrF3N3 [M + H]+ 332, 334, found 332, 334. NMR (400 MHz, CDCI3): delta8.68 (d, J= 4.9 Hz, 1 H), 7.79 (s, 1 H), 7.33-7.23 (m, 2 H), 7.10-7.06 (m, 2 H), 2.36 (s, 3 H).

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, 3-Bromo-5-methylaniline, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; MERCK SHARP & DOHME CORP.; ALTMAN, Michael, D.; CHILDERS, Kaleen Konrad; DI FRANCESCO, Maria Emilia; ELLIS, John Michael; FISCHER, Christian; GRIMM, Jonathan; HAIDLE, Andrew, M.; KATTAR, Solomon, D.; NORTHRUP, Alan, B.; OTTE, Ryan, D.; PETROCCHI, Alessia; SCHELL, Adam, J.; ZHOU, Hua; WO2012/154519; (2012); 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. 10485-09-3, name is 2-Bromoindene belongs to bromides-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below. Application In Synthesis of 2-Bromoindene

A 2.02 g (83.1 mmol) piece of magnesium was charged into a sufficiently dried and argon-replaced 200 mL reactor, and stirred vigorously while heating under reduced pressure for 30 minutes.Cool to room temperatureAfter that, a piece of iodine and 25 mL of tetrahydrofuran were charged and stirred. A 20 mL dilute solution of 3.92 g (20.1 mmol) of 2-bromoindene in 20 mL of tetrahydrofuran was slowly added, and the mixture was heated to reflux in an oil bath at 80 C. for 1 hour.This reaction solution was slowly added to a solution of 12.0 mL (100 mmol) of dimethylsilyldichloride in 10 mL of n-hexane under cooling with cooling, and stirring was continued for 18 hours while returning to room temperature.After distilling off the solvent of the reaction solution and unreacted dimethylsilyl dichloride, 20 mL of tetrahydrofuran and 1.90 mL (20.2 mmol) of 1,3-dimethyl-2-imidazolidinone were added to the residue.9.79 g of n-butylcyclopentadiene solution (25 wt% of tetrahydrofuran solution, 20.0 mmol) and 20 mL of tetrahydrofuran are charged into a sufficiently dried, argon-substituted 100 mL reactor, and 12.5 mL of n-butyllithium solution (hexane solution) , 1.60M, 20.0 mmol) was added and stirred at room temperature for 2 hours.This solution was added dropwise to the previously diluted reaction residue diluted solution cooled to -78 C., and stirring was continued for 17 hours while gradually returning to room temperature.Saturated aqueous ammonium chloride solution was added, the soluble matter was extracted with n-hexane, the obtained fraction was washed with saturated brine and dried over anhydrous magnesium sulfate.After magnesium sulfate is filtered, the filtrate is evaporated and the obtained residue is purified by silica gel column chromatography to obtain the target compound represented by the following formula (AL) (hereinafter referred to as compound (AL)) Was obtained as an isomer mixture of 4.65 g (yield 79%).

The synthetic route of 10485-09-3 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Mitsui Chemicals Chemicals company; Tanaka, Kenichi; Harada, yasuyuki; (44 pag.)JP2019/69920; (2019); A;,
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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. 6627-78-7, name is 1-Bromo-4-methylnaphthalene, This compound has unique chemical properties. The synthetic route is as follows., HPLC of Formula: C11H9Br

General procedure: A mixture of 3a-3g (0.1 mol for 3a-3e and 3g; 0.4 molfor 3f) and CuCN (26.87 g, 0.3 mol for 3a-3e and 3g; 21.49g, 0.24 mol for 3f) in DMF (300 mL) were stirred at 130C in N2 atmosphere for 12 h, when TLC analysis indicated completion of reaction. On cooling to room temperature, the reaction mixture was diluted with CH2Cl2 (900 mL) and the resulting mixture was further stirred for 1 h and filtered off. The filtrate was washed with 5% brine (500 mL 5), dried (Na2SO4) and evaporated on a rotary evaporator to afford a black oil, which was purified by column chromatography to afford the pureproduct 4a-4g.

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 6627-78-7.

Reference:
Article; Zhang, Xiansheng; Wu, Jingwei; Liu, Wei; Liu, Yuqiang; Xie, Yafei; Shang, Qian; Zhou, Zhixing; Xu, Weiren; Tang, Lida; Wang, Jianwu; Zhao, Guilong; Medicinal Chemistry; vol. 13; 3; (2017); p. 260 – 281;,
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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 3975-77-7 as follows. Recommanded Product: 3975-77-7

General. 1H NMR studies revealed that?supermesityl bromide? (mes*Br, S1)S7 and n-BuLi coexist in t-BuOMeover more than 18 h at room temperature, while this solvent is very slowlydeprotonated by n-BuLi with formation of isobutene. Similarly, t-BuLideprotonates t-BuOMe, leaving S1intact.When prepared from S1 withn-BuLi, mes*Li (S2)is not stable in a THF solution at ambient temperature. However, its stabilityis greatly enhanced on dilution of the THF with pentane. Moreover, a portion ofS2 will crystallize from pentane/THF(4:1)S8 and may be washedwith dry petroleum ether if pure mes*Li is required.In Et2O atroom temperature, the formation of mes*Li(S2) from S1and n-BuLiwas complete within 10 min; therefore,the traditional long reaction periods of this Br/Li interchange reaction in thesolvent Et2O can be considerably shortened, and the presence of apromoter (such as TMEDA) is unnecessary.This Et2O solution containing S2 and 1-bromobutane was stable for several hours at ambienttemperature and for at least 18 hours under argon gas in a refrigerator. Although S2in Et2O was protonated very slowly by N,N-diisopropylamine atroom temperature, proton transfer fromcyclohexylamine (pKa =41.6) to S2 was fast andquantitative. Procedure. A dry NMR tube (5 mm) was charged with mes*BrS7 (S1,80 mg, 0.24 mmol), pentane (0.40 mL), and anhydrous THF (0.10 mL), then cooled to -70 C during the addition of n-BuLi (0.37 mmol) in hexanes (0.14 mL)and for further 60 min. The colorless precipitate of S2 was washed with pentane (2 ) and then dissolved in anhydrous Et2O(0.50 mL), showing dH = 7.01 ppm for 3-/5-H of S2. The addition of cyclohexylamine (0.027 mL, 0.24 mmol) at -70 C converted S2 completely into 1,3,5-tri-tert-butylbenzene(dH = 7.31 ppm), which was isolated afterquenching with solid CO2 andaqueous workup (no acid S3) as apure, colorless powder (35 mg, 58%). This indicates that pKa> 41.6 for S2. A similar run with N,N-diisopropylamine(ca. 2 equiv, pKa = 34.4)in place of cyclohexylamine disclosed a very slow proton transfer at room temperature (ca. 30% in 10 min).

According to the analysis of related databases, 3975-77-7, the application of this compound in the production field has become more and more popular.

Reference:
Article; Knorr, Rudolf; Rossmann, Eva C.; Knittl, Monika; Boehrer, Petra; Tetrahedron; vol. 70; 34; (2014); p. 5332 – 5338;,
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Some common heterocyclic compound, 4766-33-0, name is 5-Bromonaphthalen-1-amine, molecular formula is C10H8BrN, 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. Application In Synthesis of 5-Bromonaphthalen-1-amine

To a suspension of 1-bromo-5-nitronaphthalene (2 g, 7.94 mmol) in EtOH (50 mL), a solution of NH4Cl (2.2 g, 41.1 mmol) in water (20 mL) was added, followed by iron powder (1.33 g, 23.82 mmol). The resulting mixture was stirred at 75 C. (bath temperature) for 1.5 h. Celite (3 g) was added, and the mixture was allowed to cool down to rt, diluted with CH2Cl2 (100 mL), filtered through a plug of Celite, washing with CH2Cl2 (150 mL). The filtrate was washed with brine and dried over Na2SO4. Upon evaporation of the filtrate, the crude material was redissolved in CH2Cl2 (20 mL), transferred on top of a 80 g SiO2 column, and ran with 20% to 80% EtOAc/hexane gradient. The fractions containing the product were evaporated to viscous light brown oil that quickly crystallized. Yield of 5-bromo-1-aminonaphthalene [West, R. W. J. Chem. Soc. 1925, 127, 494] 1.48 g (84%). 5-Bromo-1-aminonaphthalene (1.37 g, 6.17 mmol) was dissolved in trimethyl phosphate (760 muL, 6.5 mmol) in a 50 mL round-bottom flask, equipped with an air condenser and a CaCl2 drying tube, the apparatus was flushed with nitrogen, and the mixture was heated at 200 C. (bath temperature) for 1.5 h. The flask was then allowed to cool below 100 C., 1 N NaOH (20 mL) was added, the resulting suspension was sonicated briefly and stirred at rt overnight. The mixture was diluted with brine, extracted with CH2Cl2 (3¡Á50 mL), the combined extracts were dried over Na2SO4. The product was isolated by column chromatography (100 g of SiO2, gradient 10% to 50% CH2Cl2/hexane) to yield 1-bromo-5-(dimethylamino)naphthalene 28a [West, R. W. J. Chem. Soc. 1925, 127, 494] as a light-orange viscous oil (1.29 g, 84%). 1H NMR (301 MHz, CDCl3): delta 8.26 (dt, J=8.6, 1.0 Hz, 1H), 7.95 (dt, J=8.6, 0.9 Hz, 1H), 7.78 (dt, J=7.4, 1.0 Hz, 1H), 7.51 (ddd, J=8.5, 7.5, 0.7 Hz, 1H), 7.32 (ddd, J=8.4, 7.3, 0.7 Hz, 1H), 7.14 (dd, J=7.6, 1.0 Hz, 1H), 2.90 (s, 6H) ppm. 13C NMR (76 MHz, CDCl3): delta 151.3, 133.4, 130.4, 130.1, 127.3, 125.4, 124.3, 123.3, 122.0, 115.0, 45.5.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 4766-33-0, its application will become more common.

Reference:
Patent; Max-Planck-Gesellschaft zur Foerderung der Wissenschaften e. V.; SEDNEV, Maksim; BUTKEVICH, Alexey; SHOJAEI, Heydar; BELOV, Vladimir; HELL, Stefan; WURM, Christian; KAMIN, Dirk; (68 pag.)US2018/223102; (2018); A1;,
Bromide – Wikipedia,
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