Month: December 2020

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;,
Bromide – Wikipedia,
bromide – Wiktionary

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;,
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. 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;,
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. 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;,
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 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;,
Bromide – Wikipedia,
bromide – Wiktionary

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,
bromide – Wiktionary

Electric Literature of 10269-01-9, 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. 10269-01-9, name is (3-Bromophenyl)methanamine belongs to bromides-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below.

[0241] 1-(3-Bromobenzyl)-2,2,5,5-tetramethyl-1,2,5-azadisilolidine (3.1). The procedure developed by Magnus et al. was followed.5 To a solution containing 2.228 g (11.98 mmol) of 3-bromobenzylamine in 10 mL of dichloromethane was added 3.4 mL (24 mmol) of triethylamine. The solution was stirred for 30 min and then treated with a solution containing 2.579 g (11.98 mmol) of 1,1,4,4-tetramethyl-1,4-dichlorosilethylene in 5 mL of dichloromethane. The reaction mixture was stirred for 3 h and then poured into 100 mL of saturated sodium dihydrogen phosphate. The reaction mixture was extracted with three 50 mL portions of dichloromethane, then dried (MgSO4), and concentrated under reduced pressure. The residue was distilled at 160 C. to give 3.1 as a clear colourless oil: yield 2.510 g (64%). 1H NMR (200 MHz, acetone-d6): delta 0.00 (s, 12H), 0.78 (s, 4H), 4.06 (s, 2H), 7.20-7.48 (m, 4H). 13C NMR (50.3 MHz, Acetone-d6): delta -0.26, 8.01, 45.59, 122.15, 126.10, 129.35, 129.53, 130.69, 146.01. IR (thin film): 3388, 2953, 1666, 1251, and 1132 cm-1. MS (CI): m/z=312.

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-Bromophenyl)methanamine, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; Valliant, John F.; Dorff, Peter N.; Chirakal, Raman; US2004/260073; (2004); A1;,
Bromide – Wikipedia,
bromide – Wiktionary

Related Products of 40787-48-2, 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 40787-48-2 as follows.

Finally, the final product d was obtained by Suzuki coupling reaction: 9 mmol of 9-benzoquinone-10 borate was obtained.1.5 mmol of 1,4-dibromo-2,5-diethylbenzene, 0.36 mmol of tetrakis(triphenylphosphine)palladium, 60 mL of toluene,15 mL of ethanol, 333 mmol of K2CO, (formed as a solution with 15 mL of water), and added to the reaction flask.The system was then evacuated under reflux of nitrogen at 110 C for 24 hours.After completion of the reaction, the methanol was subjected to hot-washing suction filtration, toluene to recrystallization, and sublimation to obtain the final product d, yield 42%.

According to the analysis of related databases, 40787-48-2, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Shaanxi Normal University; Hu Jianyong; Zhang Jiali; (19 pag.)CN108383693; (2018); A;,
Bromide – Wikipedia,
bromide – Wiktionary

Reference of 626-88-0, A common heterocyclic compound, 626-88-0, name is 1-Bromo-4-methylpentane, molecular formula is C6H13Br, 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.

Entry 7: 3,7-dimethyloctan-2-one (0.5 mmol, 78.1 mg). The remote product was 7-hydroxy-3,7-dimethyloctan-2-one (21), and the proximal product was 3-hydroxy-3,7-dimethyloctan-2-one. Purification by flash chromatography (35% EtOAc/hexanes), run 1 (46.0 mg, 0.267 mmol, 53%), run 2 (43.1 mg, 0.250 mmol, 50%). Average: 52%. Recovered starting material (rSM): 14.2 mg, 0.183 mmol, 18%. [Remote:Proximal]>99:1. Authentic proximal oxidation product was obtained by treating 1-bromo-4-methylpentane (1 equiv.) with Mg turnings (1 equiv.), followed by 2,3-butandione (1 equiv.) at -78 C. The reaction was quenched H2O, extracted with CH2Cl2 and purified by column chromatography (15% EtOAc/hexanes) to yield 3-hydroxy-3,7-dimethyloctan-2-one.

The synthetic route of 626-88-0 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; The Board of Trustees of the University of Illinois; US2011/15397; (2011); A1;,
Bromide – Wikipedia,
bromide – Wiktionary