Month: August 2021

Reference of 583-75-5,Some common heterocyclic compound, 583-75-5, name is 4-Bromo-2-methylaniline, molecular formula is C7H8BrN, 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 mixture of 4-bromo-2-methylaniline (0.0268 mol), intermediate E3, palladium (0) acetate (0.00537 mol), tri-o-tolylphosphine (0.0268 mol) and acrylonitrile (0.0896 mol) in triethylamine (0.107 mol) and acetonitrile (70 ml) was stirred at 140C in a stainless-steel bomb for 18h. After cooling, the mixture was filtered over celite and the filtrate was poured in water and extracted with CH2Cl2. The organic layer was dried over magnesium sulfate, filtered and the solvent evaporated. The residue was purified by column EPO chromatography over silica gel (eluent: CHiCyCyclohexane 50/50; 35-70 mum). The pure fractions were collected and the solvent evaporated. Yield: 3.2 g of intermediate F3 (75 %, melting point : 105C)

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 4-Bromo-2-methylaniline, its application will become more common.

Reference:
Patent; TIBOTEC PHARMACEUTICALS LTD.; ARTS, Frank Xavier Jozef Herwig; WO2006/45828; (2006); 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. 937046-98-5, name is 7-Bromopyrrolo[2,1-f][1,2,4]triazin-4-amine, This compound has unique chemical properties. The synthetic route is as follows., Recommanded Product: 7-Bromopyrrolo[2,1-f][1,2,4]triazin-4-amine

To a stirred suspension of Intermediate B (2.50 g, 9.39 mmol) in THF (50 ml_) was added chlorotrimethylsilane (2.98 mL, 23.47 mmol), dropwise. The mixture was stirred at rt for 3 h and 2-propylmagnesium chloride (2M in THF; 24.64 mL, 49.29 mmol) was added dropwise. The suspension immediately went into solution. The mixture was stirred at rt for 3 h and 1-Boc-3-piperidone (3.51 g, 17.60 mmol) was added in one portion. The reaction was stirred at rt for 16 h. The reaction was poured over a mixture of ice and saturated, aqueous ammonium chloride (250 mL). The mixture was allowed to warm to rt and was extracted with EtOAc (3 x 100 mL). The combined organic layers were washed with brine, dried (Na2SO4), and concentrated to dryness. The crude residue was purified by ISCO chromatography using a gradient of 50 to 75% ethyl acetate in hexanes to afford 2.77 g (71%) of the desired product. ES-MS m/z 334.08 [M+H]+, HPLC RT (min) 0.97.

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 937046-98-5.

Reference:
Patent; BAYER PHARMACEUTICALS CORPORATION; WO2007/56170; (2007); A2;,
Bromide – Wikipedia,
bromide – Wiktionary

Application of 2576-47-8, 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. 2576-47-8, name is 2-Bromoethylamine hydrobromide belongs to bromides-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below.

General procedure: A mixture of aniline (or PhNHEt) (0.05 mol)), 2-bromoethyl- (or 3-bromopropyl)amine hydrobromide and water (6 mL) was heated to 95 C (ina bath), Then, NaHCO3 was added in small portions with stirring. After ~15 min (at 95 C), the reaction mixture was refluxed with stirring using a heating mantle until reaction reached completion. The amount of hydrobromide and NaHCO3 and the timeof heating are given in Table 1. Still warm reaction mixture was diluted with 50% aqueous KOH (11 mL) and water (16 mL). The organic layer was separated, the aqueous layer was saturated with NaCl and extracted with chloroform (4×20 mL), each timeadding NaCl into the aqueous phase. The combined organic layers were dried with MgSO4 and fractionally distilled in vacuo.

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-Bromoethylamine hydrobromide, other downstream synthetic routes, hurry up and to see.

Reference:
Article; Vasilyeva; Vorobyeva; Osipov; Russian Chemical Bulletin; vol. 65; 9; (2016); p. 2211 – 2215; Izv. Akad. Nauk, Ser. Khim.; 9; (2016); p. 2211 – 2215,5;,
Bromide – Wikipedia,
bromide – Wiktionary

4333-56-6, name is Bromocyclopropane, belongs to bromides-buliding-blocks compound, is considered to be a conventional heterocyclic compound, which is widely used in drug synthesis. The chemical synthesis route is as follows. Product Details of 4333-56-6

Step (i) of Example W1: 4-Cyclopropylmethylpyridine A solution of 19.5 ml (200 mmol) of 4-picoline in tetrahydrofuran (120 ml) was cooled to -78C. Lithium diisopropylamide (2 M heptane, tetrahydrofuran, ethylbenzene solution) (200 ml) was added dropwise to the cooled solution over a period of 20 min. The mixture was then stirred at -40C for 20 min and was cooled to -78C. Cyclopropylbromide (16.0 ml, 200 mmol) was added dropwise to the reaction solution over a period of 25 min, and the mixture was stirred at -78C for one hr. The reaction solution was then added to 300 ml of a saturated aqueous ammonium chloride solution, and the mixture was satisfactorily washed with 100 ml of water. The solution was extracted twice with 200 ml of ethyl acetate, and the extract was dried over anhydrous sodium sulfate. After filtration, the filtrate was concentrated, and the residue was distilled under the reduced pressure (8 mmHg, 86 to 87C). The distillation residue was purified by column chromatography on silica gel (hexane : ethyl acetate = 70 : 30) to give 17.6 g (yield 66%) of the title compound. 1H-NMR (400 MHz, CDCl3) delta: 0.19-0.25 (2H, m), 0.55-0.61 (2H, m), 0.93-1.04 (1H, m), 2.54 (2H, d, J = 7.1 Hz), 7.17-7.22 (2H, m), 8.47-8.52 (2H, m). MS (FAB) m/z 134 [M+H]+.

The synthetic route of 4333-56-6 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Meiji Seika Kaisha Ltd.; EP2151447; (2010); 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 24358-62-1 as follows. Safety of 1-(4-Bromophenyl)ethylamine

To a mixture of the compound represented by the structural formula (Q-1) (5.0 g, 25 mmol) and NaOH (2.0 g, 50 mmol) in water (18 mL) and isopropanol (18 mL), the compound represented by the structural formula (Q-1A) (3.31 g, 27.5 mmol) was added dropwise at 20C, and the resulting mixture was stirred at the same temperature for 0.5 hour. Then, the mixture was cooled to 10C, water (50 mL) was added to the mixture, and the resulting mixture was filtered to give white solid. The resulting solid was dissolved in EA (150 mL), and the solution was washed with brine (50 mL), dried over anhydrous sodium sulfate, filtered, and concentrated to give N-[(4-bromophenyl)ethyl]-2,2-dimethylpropanamide as white solid (6.27 g, yield 88%). 1H-NMR Spectrum (300MHz, CDCl3):delta (ppm): 7.43-7.47 (m, 2H), 7.14-7.19 (m, 2H), 5.75 (brs, 1H), 5.02-5.07 (m, 1H), 1.40-1.46 (m, 3H), 1.21 (s, 9H)

According to the analysis of related databases, 24358-62-1, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Juntendo Educational Foundation; HIRAMATSU Keiichi; MORIMOTO Yuh; BABA Tadashi; HAYAKAWA Isao; (76 pag.)EP2987787; (2016); A1;,
Bromide – Wikipedia,
bromide – Wiktionary

Reference of 556-96-7, 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 556-96-7 as follows.

General procedure: Styrene (5.0 mmol), aryl halide (5.0 mmol), potassium carbonate(10.0 mmol) and the palladium complex (0.003 mmol) weremixed in methanol (20 ml) and refluxed for 2 h as mentioned inTable 5. At the end of the reaction solvent was evaporated andthe residue was poured into water and extracted in diethyl ether,dried over anhydrous Na2SO4 and pass through 12// silica column (60-120 mesh). After evaporation of the ether, solid pure productswere obtained. The yields of the products obtained from all thereactions were determined after isolation and characterized by1H NMR spectra (Table 5).

According to the analysis of related databases, 556-96-7, the application of this compound in the production field has become more and more popular.

Reference:
Article; Das, Uttam; Pattanayak, Poulami; Patra, Debprasad; Brandao, Paula; Felix, Vitor; Chattopadhyay, Surajit; Polyhedron; vol. 110; (2016); p. 165 – 171;,
Bromide – Wikipedia,
bromide – Wiktionary

Adding a certain compound to certain chemical reactions, such as: 2255-80-3, name is 4-Bromo-7-methylbenzo[c][1,2,5]thiadiazole, 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 2255-80-3, name: 4-Bromo-7-methylbenzo[c][1,2,5]thiadiazole

Synthesis of Compound A-4-Bromo-7-dibromomethyl-2,1,3-benzothiadiazole A mixture of 4-bromo-7-methyl-2,1,3-benzothiadiazole (45.82 g, 200 mmol), AlBN (6.57 g, 40 mmol), and NBS (106.2 g, 600 mmol) in chlorobenzene (400 mL) was stirred and heated at 80 C. for 4 hours. After cooling to room temperature, the reaction mixture was filtered to remove the solid succinimide, and then the filtrate was washed with water and brine, dried over anhydrous MgSO4, and filtered. The solvent of the filtrate was removed by rotary evaporation, and the crude product was purified by column chromatography on silica gel with CH2Cl2/hexane (v/v, 1:3) as eluent to afford Compound A as a white solid (56.1 g, 83%). The analytical data obtained from Compound A are listed below. M.p. 119-120 C.; IR (KBr) v 3001, 2922, 1524, 1481, 1315, 1274, 1185, 1097, 937, 880 cm-1; 1H NMR (CDCl3, 400 MHz) delta 7.97-7.90 (m, 2H), 7.40 (s, 1H); 13C NMR (CDCl3, 100 MHz) delta 152.8, 149.6, 133.4, 131.8, 129.4, 115.8, 33.9; HRMS (m/z, FAB+) Calcd. for C7H379Br3N2S 383.7567. found 383.7542, Calcd. for C7H379Br281Br1N2S 385.7547. found 385.7553, Calcd. for C7H379Br181Br2N2S 387.7526. found 387.7524, Calcd. for C7H381Br3N2S 389.7506. found 389.7536.

At the same time, in my other blogs, there are other synthetic methods of this type of compound, 4-Bromo-7-methylbenzo[c][1,2,5]thiadiazole, and friends who are interested can also refer to it.

Reference:
Patent; Wong, Ken-Tsung; Lin, Hao-Wu; Lin, Li-Yen; Lin, Francis; Chen, Yi-Hong; Chiu, Shi-Wen; US8802975; (2014); B2;,
Bromide – Wikipedia,
bromide – Wiktionary

Electric Literature of 608-30-0, 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. 608-30-0 name is 2,6-Dibromoaniline, 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.

Under a nitrogen atmosphere, 1.2 mmol alpha,alpha-dione-2,3:5,6-bis(pentamethylene)pyridine, 1.0 mmol of CoCl2, 2.5 mmol of 2,6-dibromoaniline dissolved in 10mL glacial acetic acid, reflux reaction at 120 C (under reflux reaction) for 4 hours. After completion of the reaction, the mixture was cooled to room temperature, and 30 mL of anhydrous ether was added thereto, followed by stirring for 2 hours. Filtered, washed with ether and dried. A brown powder was obtained in a yield of 60.7%.

At the same time, in my other blogs, there are other synthetic methods of this type of compound, 2,6-Dibromoaniline, and friends who are interested can also refer to it.

Reference:
Patent; Institute of Chemistry, Chinese Academy of Sciences; Du, Shizhen; Zhang, Wenjuan; Sun, Wenhua; (29 pag.)CN106432356; (2017); A;,
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. 327-52-6, name is 1-Bromo-2,4,5-trifluorobenzene, A new synthetic method of this compound is introduced below., Formula: C6H2BrF3

[0113] Into a 100 mL three- necked flask were added 4.62 g 1- bromo- 2, 4, 5- trifluorobenzene (0.022 mol) andanhydrous tetrahydrofuran (50 mL) . The resulting mixture was cooled to- 20 C. The solution of isopropylmagnesiumbromide (22 mmol) in tetrahydrofuran (22 ml, 1 M THF) was slowly added dropwise under nitrogen. After the additionwas completed, the reactants were maintained at- 20 C for later use.[0114] Cuprous bromide – dimethyl sulfide (0.41 g, 0.002 mol) was suspended in 5 ml anhydrous tetrahydrofuran. Theresulting mixture was cooled to -5 C. The Grignard reagent as obtained above was slowly added dropwise undernitrogen. After 15 min, a solution of the acridine compound as shown in the above reaction formula (3.26 g, 0.015 mol)in 30 mL tetrahydrofuran was slowly added dropwise. After additional 5 min, 50 mL saturated solution of ammoniachloride was added to quench the reaction. Into this obtained solution was added 50 mL ethyl acetate for an extraction.The separated water layer was extracted with another 50 mL ethyl acetate. The obtained organic layers were collectedtogether and further washed with saturated solution of sodium chloride and then dried over anhydrous sodium sulfate,followed by filtration and concentration to obtain a crude product which was further treated by column chromatographyto obtain a compound (4.29 g, yield 82%).1H NMR (400 MHz, CDCl3) delta 7.15?6.94 (m, 1 H), 6.88 (d, J = 6.8 Hz, 1H), 4.47 (d, J = 8.9 Hz, 1H), 4.00?3.80 (m, 1 H),2.92?2.76 (m, 1H), 2.76?2.64 (m, 1H), 2.64?2.44 (m, 2H), 2.06 (d, J =14.6 Hz, 3H), 1.84 (s, 1H), 1.66 (qd, J = 14.0, 8.0Hz, 1H), 1.47?1.31 (m, 9H). Ms (M++1): 350.

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; Zhejiang Hisoar Pharmaceutical Co., Ltd; PAN, Xianhua; LI, Weijin; ZHANG, Qunhui; RUAN, Libo; YU, Wansheng; DENG, Fei; MA, Tianhua; HUANG, Mingwang; HE, Minhuan; EP2647624; (2013); A1;,
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. 656-64-4, name is 3-Bromo-4-fluoroaniline, A new synthetic method of this compound is introduced below., Formula: C6H5BrFN

To a 500 mL three-necked flask was placed HS-VI (14.9 g), 1,4-dioxane (100 mL), water (100 mL), and warmed to 50 C. 3-Bromo-4-fluoroaniline (11.4 g) was added, and the mixture was stirred at 50 to 60 C for 10 minutes. Sodium bicarbonate (7.7 g) was dissolved in water (100 mL), and slowly added dropwise to the reaction flask, and the internal temperature was controlled at 50 to 60 C, and the addition was completed in 0.5 hour. Stirring was continued for 1 hour and the reaction was completed. The oil bath was removed, cooled to room temperature, ethyl acetate (200 mL) was added and stirred for 10 min. The aqueous layer was extracted once with ethyl acetate, the organic layers were combined, washed once with brine, dried over sodium sulfate, filtered, and concentrated to give 21.5 g of a yellow solid, a yield of 89.7%.

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; Shanghai Hansen Bio-pharmaceutical Technology Co., Ltd.; Liu Fuping; Zhang Jingtao; Wu Liyuan; Sun Changan; Bao Rudi; (33 pag.)CN109956914; (2019); A;,
Bromide – Wikipedia,
bromide – Wiktionary