Month: June 2021

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. 103-64-0, name is (2-Bromovinyl)benzene, A new synthetic method of this compound is introduced below., COA of Formula: C8H7Br

To a solution of an appropriate amount of an organic solvent (a mixture of N, N-dimethylformamide (DMF) and polyethylene glycol 200 (PEG-200) in a volume ratio of 4: 1)100 mmol of the compound of formula (I)40 mmol of the compound of formula (II)11 mmol of catalyst bis (triphenylphosphine) cyclopentadienyl ruthenium chloride,100 mmol Oxidant Bis (trifluoroacetic acid) iodobenzene (PhI (TFA) 2),20 mmol of organic ligands L1,60 mmol of base,5,7-triazabicyclo [4.4.0] dec-5-ene (TBD) and 10 mmol activator niobium pentachloride,Then the mixture was warmed to 70 C with stirring, and the reaction was stirred at that temperature for 12 hours;;After completion of the reaction, the reaction system is naturally cooled to room temperature and the pH is adjusted to neutral, filtered and the filtrate is saturated Washed with brine and extracted with ethyl acetate 2-3 times. The combined organic phases were dried over anhydrous sodium sulfate and concentrated under reduced pressure. The residue was passed through Silica gel column chromatography eluting with a 1: 2 by volume mixture of chloroform and petroleum ether to give a compound of the above formula (III) The yield was 89.5%.

The synthetic route of 103-64-0 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Huang Cheng; Bu Gonggaofamingren; (11 pag.)CN106278838; (2017); A;,
Bromide – Wikipedia,
bromide – Wiktionary

Adding a certain compound to certain chemical reactions, such as: 51437-00-4, name is 4-Bromo-1-fluoro-2-methylbenzene, 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 51437-00-4, category: bromides-buliding-blocks

General procedure: An oven dried two-necked round bottom flask was charged with aryl halide (1mmol) and K3PO4 (2mmol), evacuated and backfilled with argon. The azole compound (1mmol) and 2mL of DMSO were added under argon. After that Cu-NP (1.6mmol) was added and the flask was again backfilled with argon. The flask was then immersed in a preheated oil bath at 80C until the conversion was completed (detected by TLC). The cooled mixture was partitioned between ethyl acetate (10mL) and saturated NH4Cl (10mL). The aqueous layer was extracted with ethyl acetate (2×10mL), the organic layer was washed with brine (20mL), dried over anhydrous Na2SO4 and concentrated in vacuum. The residue was purified by column chromatography on silica gel using ethyl acetate in hexane (1.5-10%) as eluent to afford the desired product. All the products have been characterized by 1H NMR, 13C NMR, and mass spectroscopy. For new products, FTIR data were also recorded.

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

Reference:
Article; Pai, Gita; Chattopadhyay, Asoke P.; Tetrahedron Letters; vol. 57; 29; (2016); p. 3140 – 3145;,
Bromide – Wikipedia,
bromide – Wiktionary

Adding a certain compound to certain chemical reactions, such as: 452-92-6, name is 5-Bromo-2,4-difluoroaniline, 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 452-92-6, category: bromides-buliding-blocks

Potassium o-ethyl carbondithioate (5.36 g, 33.5 mmol), 5-bromo-2,4- difluoroaniline (5.8 g, 27.9 mmol) were combined in dry N-methyl-2-pyrrolidone (NMP; 40 mL) and heated to 100C for 18 h. After cooling, the mixture was partitioned between EtOAc (50 mL) and water (30 mL). The aqueous, phase was extracted with EtOAc (30 mL) and the combined organic phases were washed water (2 x 25 mL), satd NaCl (25 mL), dried and concentrated to give the intermediate thiol (5.4 g) as a tan solid. This material was combined in methanol (120 mL) with nickel chloride hexahydrate (3.3 g, 14 mmol)and zinc powder (3.7 g, 56 mmol), heated to reflux and treated dropwise with concentrated HC1 (20 mL). The reaction mixture was heated for 2 h after the addition was complete. The cooled mixture was stirred with EtOAc (200 mL) and treated with concentrated aq ammonia until the pH was > 10. The organic phase was washed with satd NaCl (40 mL), dried and concentrated. Purification by chromatography with 0-40% EtOAc-hexanes gave the title compound as a yellow solid (3.2 g, 47%): mp 86-88 C; NMR (400 MHz, DMSO-d6) delta 9.44 (s, 1H), 8.47 (d, / = 6.3 Hz, 1H), 8.30 (d, J = 8.6 Hz, 1H); 19F NMR (376 MHz, DMSO-d6) delta -111.18; EIMS m/z 232.

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; DOW AGROSCIENCES LLC; BELL, Jared; BUYSSE, Ann M.; DAEUBLE, John F.; ECKELBARGER, Joseph D.; EPP, Jeffrey B.; IRVINE, Nicholas M.; KISTER, Jeremy; LO, William C.; LOSO, Michael R.; LOWE, Christian T.; ROHANNA, John C.; SATCHIVI, Norbert M.; SIDDALL, Thomas L.; STEWARD, Kimberly M.; YERKES, Carla N.; (281 pag.)WO2019/84353; (2019); A1;,
Bromide – Wikipedia,
bromide – Wiktionary

Reference of 10269-01-9, A common heterocyclic compound, 10269-01-9, name is (3-Bromophenyl)methanamine, molecular formula is C7H8BrN, 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.

General procedure: HATU(1.00 g, 2.63 mmol, 1.05 equiv) was added to a stirred solution of the startingamine (2.50 mmol, 1.0 equiv), N,N-diisopropylethylamine(1.30 mL, 7.55 mmol, 3.0 equiv) and picolinic acid (325 mg, 2.63 mmol,1.05 equiv) in methylene chloride (25 ml) and the mixture was stirred at roomtemperature overnight. In the morning, the reaction mixture was transferred toseparating funnel with 25 mL H2O and extracted twice with methylenechloride (2 x 25 mL). The combined organic phase was dried over Na2SO4,filtered and solvents were removed invacuo. The residue was purified by column chromatography over silica gelusing gradient elution (40 to 100% Et2O in hexane).

The synthetic route of 10269-01-9 has been constantly updated, and we look forward to future research findings.

Reference:
Article; O’Donovan, Daniel H.; De Fusco, Claudia; Spring, David R.; Tetrahedron Letters; vol. 57; 27-28; (2016); p. 2962 – 2964;,
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. 4101-68-2, name is 1,10-Dibromodecan, This compound has unique chemical properties. The synthetic route is as follows., Recommanded Product: 4101-68-2

To a 500 rnL rmmd-bottom flask was added L l 0-dibromodecane 223a (24. 2 g, 80.655 mmol, 3.00 equiv.), acetone (1.50 mL), 2-potassio-2,3-dihydro-lH-isoindole-1 ,3-dione 223b(5 g, 26.99 mmol, 1.00 equiv.), and potassium carbonate (l 1.2 g, 81.04 mmoL 3.00 equiv.).TI1e resulting mixture v.·as stirred at 60C for 16h and concentrated. The residue was purifiedby silica gel column chromatography eluting with ethyl acetate/petroleum ether (l. 10) to give2-(10-bromodecyl)-2,3-dihydro-lH-isoindole-1,3-dione 223c (8.5g, 86~6) as a white solid.

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 4101-68-2.

Reference:
Patent; ARDELYX, INC.; CHAO, Jianhua; JAIN, Rakesh; HU, Lily; LEWIS, Jason Gustaf; BARIBAULT, Helene; CALDWELL, Jeremy; (582 pag.)WO2018/39386; (2018); A1;,
Bromide – Wikipedia,
bromide – Wiktionary

Reference of 13633-25-5,Some common heterocyclic compound, 13633-25-5, name is 1-Bromo-4-phenylbutane, molecular formula is C10H13Br, 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.

General procedure: To a solution of iminodiacetic acid hydrochloride (2 mmol) in MeOH (10 mL) were added NEt3 (6 mmol) and the corresponding bromide derivative (2 mmol). The mixture was stirred overnight at room temperature. The crude product was purified by preparative HPLC.

The synthetic route of 13633-25-5 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Charton, Julie; Gauriot, Marion; Totobenazara, Jane; Hennuyer, Nathalie; Dumont, Julie; Bosc, Damien; Marechal, Xavier; Elbakali, Jamal; Herledan, Adrien; Wen, Xiaoan; Ronco, Cyril; Gras-Masse, Helene; Heninot, Antoine; Pottiez, Virginie; Landry, Valerie; Staels, Bart; Liang, Wenguang G.; Leroux, Florence; Tang, Wei-Jen; Deprez, Benoit; Deprez-Poulain, Rebecca; European Journal of Medicinal Chemistry; vol. 90; (2015); p. 547 – 567;,
Bromide – Wikipedia,
bromide – Wiktionary

Adding a certain compound to certain chemical reactions, such as: 460-00-4, name is 1-Bromo-4-fluorobenzene, 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 460-00-4, Product Details of 460-00-4

General procedure: A 10 mL vial was charged with CuI (9.5 mg, 0.05 mmol), PSAP (30 mg,0.05 mmol, > 100 mesh), K3PO4 (424 mg, 2 mmol), aryl bromides (1mmol), amines (1.5 mmol), DEG (2 mL), and a magnetic stir bar. The vessel was sealed with a septum and placed into a preheated oil batchat 70 C. The reaction mixture was held at this temperature for 14 hours. After cooling to r.t., the reaction mixture was filtered, and the precipitates were thoroughly washed with water and EtOAc (3 × 20mL). The combined organic phases were washed with water and brine, dried over anhydrous Na2SO4, and concentrated in vacuo. Theresidue was purified using flash column chromatography on silica gel(eluting with petroleum ether/EtOAc) to afford the desired products.

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:
Article; Yi, Zhou; Huang, Manna; Wan, Yiqian; Zhu, Xinhai; Synthesis; vol. 50; 19; (2018); p. 3911 – 3920;,
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. 33070-32-5, name is 5-Bromo-2,2-difluorobenzodioxole, A new synthetic method of this compound is introduced below., COA of Formula: C7H3BrF2O2

Example 1A 2,2-difluoro-2H-1,3-benzodioxol-5-ol To a mixture of 5-bromo-2,2-difluorobenzo[d][1,3]dioxole (10 g, 42.2 mmol), 2-di-tert-butylphosphino-3,4,5,6-tetramethyl-2′,4′,6′-triisopropyl-1,1′-biphenyl (2.028 g, 4.22 mmol) and potassium hydroxide (4.74 g, 84 mmol) was added degassed water (10 mL). The reaction mixture was sparged with a nitrogen stream for 5 minutes. To the reaction mixture was added a degassed solution of tris(dibenzylideneacetone)dipalladium(0) (0.773 g, 0.844 mmol) in dioxane (10 mL). The combined reaction mixture was sparged with nitrogen for 5-7 minutes. The reaction vial was capped and stirred at 100 C. overnight (16 hours). The reaction mixture was cooled to ambient temperature, and partitioned between ethyl acetate and 1 N HCl solution. The organic fractions were combined and washed with brine, dried over anhydrous sodium sulfate, filtered, and concentrated in vacuo, maintaining a bath temp at or below 25 C. The residue was purified by flash chromatography using a 220 g silica gel cartridge, eluting with 25-75% dichloromethane/heptanes to afford 6.02 g of the title compound (82% yield). 1H NMR (400 MHz, CDCl3) delta ppm 5.51 (s, 1H), 6.50 (dd, J=8.6, 2.5 Hz, 1H), 6.63 (d, J=2.4 Hz, 1H), 6.90 (dd, J=8.7, 1.4 Hz, 1H); MS (ESI-) m/z 173.1 (M-H)-.

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; AbbVie S.a.r.l.; Galapagos NV; Altenbach, Robert J.; Bogdan, Andrew; Cowart, Marlon D.; Esmieu, William Ramesh; Gfesser, Gregory A.; Greszler, Stephen N.; Koenig, John R.; Kym, Philip R.; Liu, Bo; Malagu, Karine Fabienne; Patel, Sachin V.; Scanio, Marc J.; Searle, Xenia B.; Voight, Eric; Wang, Xeuqing; Yeung, Ming C.; (202 pag.)US2017/15675; (2017); A1;,
Bromide – Wikipedia,
bromide – Wiktionary

Synthetic Route of 1154740-48-3, 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. 1154740-48-3, name is 6-Bromo-5-methyl-3,4-dihydro-2H-benzo[b][1,4]oxazine belongs to bromides-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below.

A well stirred DMF (15 ml.) solution of the arylbromide 5e (0.50 g, 2.19 mmol, 1 eq), potassium acetate (0.728 g, 7.67 mmol, 3.5 eq) and bis(pinacolato)diborane (0.83 g, 3.3 mmol, 1.5 eq) is degassed by bubbling Ar through the solution for about 20 min. PdCI2(dppf)-DCM (320 mg, 0.44 mmol, 0.20 eq) is added and degassing is continued for about 15 min. The system is sealed (teflon screw cap vessel) under Ar and heated to ~90C for about 5 h. The reaction mixture is allowed to cool to RT, dilute with EtOAc (150 ml_), washed with brine (3 x 100 ml_) and water (2 x 100 ml_), dried over anhydrous MgSO4, filtered and concentrated to dryness. The residue is purified by CombiFlash Companion (EtOAc/hexanes) to give the desired boronate 5f (389 mg, 65% yield) as a yellowish waxy solid.

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, 6-Bromo-5-methyl-3,4-dihydro-2H-benzo[b][1,4]oxazine, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; BOEHRINGER INGELHEIM INTERNATIONAL GmbH; WO2009/62308; (2009); 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. 141474-37-5, name is 2,4-Dibromo-6-fluoroaniline, This compound has unique chemical properties. The synthetic route is as follows., Safety of 2,4-Dibromo-6-fluoroaniline

2,4-dibromo-6-fluoro-phenylamine 2.69 g (10.0 mmol), phenylboronic acid 2.68 g (22.0 mmol), Pd(PPh3)4 (Tetrakis(triphenylphosphine)palladium(0)) 0.58 g ( 0.5 mmol) and K2CO3 6.21 g (45.0 mmol) were dissolved in 40 mL of a THF (tetrahydrofuran)/H20 (2/1) mixed solution, and stirred at 80C for 5 hours. After cooling the reaction solution to room temperature, it was extracted 3 times with 40 mL of water and 40 mL of diethyl ether. The organic layer obtained therefrom was dried over magnesium sulfate, and the residue obtained by evaporating the solvent was separated and purified through silica gel column chromatography to obtain intermediate I-2 (2.26 g, 86% yield).

According to the analysis of related databases, 141474-37-5, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Samsung Display Co., Ltd.; Kim Su-yeon; Hwang Seok-hwan; Kim Yeong-guk; Jeong Hye-jin; Im Jin-o; Han Sang-hyeon; Jeong Eun-jae; Park Jun-ha; Lee Eun-yeong; Lee Jong-hyeok; (74 pag.)KR102105076; (2020); B1;,
Bromide – Wikipedia,
bromide – Wiktionary