Tag: M.W=200-300

Adding a certain compound to certain chemical reactions, such as: 24358-62-1, name is 1-(4-Bromophenyl)ethylamine, 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 24358-62-1, Application In Synthesis of 1-(4-Bromophenyl)ethylamine

To a solution of 2-bromoacetamide 6 (827mg, 5.88 mmol), and 4-bromobenzylethylamine 15 (1.00 g, 4.90 mmol) in MeOH (5ml) and CH2Cl2 (5ml) at room temperature was added Hunig’s base (5ml). The mixture was stirred at 50-60 C for 16h. Water (30mL) was added and the mixture was extracted with CH2Cl2 (4 x 30ml) and dried over Na2SO4 to provide 1.27 g amide 16 as white crystals in 100% yield. This product was used without further purification in the next step. 1HNMR (300 MHz, CDCl3, ppm): delta 7.38 (d, J=8Hz, 2H), 7.09 (d, J=8Hz, 1H), 6.77 (s br, 1H), 5.69 (s br, 1H), 3.67 (q, J=7Hz, 1H), 3.07 (s, 2H), 1.29 (d, J=7Hz, 3H).

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

Reference:
Patent; RIB-X PHARMACEUTICALS, INC.; WO2005/12270; (2005); A2;,
Bromide – Wikipedia,
bromide – Wiktionary

Reference of 1074-24-4, 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 1074-24-4 as follows.

Iodine (78 mg, 0.33 mmol) was added to p-xylene (6.13 mL, 50.0 mmol), the mixture was cooled to 0 °C, and bromine (5.20 mL, 101 mmol) was added dropwise over 10 min. The ice bath was removed and the reaction stirred at rt for 16 h in the absence of light. The reaction was quenched with 20percent aq. KOH and stirred for 15 min while the solution became colorless. The solid precipitate was filtered and rinsed 2 x with 100 mL of H2O. The solids were recrystallized in ethanol to afford a white solid (9.19 g, 70percent). 1H NMR (CDCl3): delta 7.40 (s, 2H), 2.34 (s, 6H). 1,4?dibromo-2,5-dimethylbenzene (5.93 g, 22.5 mmol) and KMnO4 (15.72 g, 99.5 mmol) were added to 80 mL of t-BuOH:H2O (1:1). Celite (14 g) was added to the flask and the reaction was refluxed for 18 h. The reaction mixture was cooled to rt, filtered over celite and the filter was washed with hot H2O (100mL) and EtOAc (50mL). The filtrate was then acidified to pH=1 with conc. HCl. The white suspension was then extracted 3x with 100 mL of EtOAc. The combined organic extracts were dried over MgSO4 and excess solvent was removed under vacuum to obtain a white solid (3.06 g, 42percent) which was not purified further. 1H NMR (DMSO-d6): delta 8.01 (s, 2H). 2,5?dibromoterephthalic acid (2.04 g, 6.30 mmol) dissolved in 35 mL of MeOH and refluxed for 30 min. Thionyl chloride (9.00 mL, 124 mmol) was then carefully added and the reaction was refluxed 12 hours. The reaction flask was cooled to room temperature, 50 mL of water was carefully added, and the reaction was extracted 3x with 75 mL of Et2O. The combined organics were washed with 3 x with 50 mL of sat. NaHCO3 and dried with MgSO4. The solvent was removed under vacuum and the solids recrystallized in MeOH to yield a white crystalline solid (1.65g, 74percent), mp = 134-136 C (lit.3 mp 134-137 C). 1H NMR (CDCl3): delta 8.06 (s, 2H), 3.96 (s, 6H). The 1H NMR matches the known spectrum.3

According to the analysis of related databases, 1074-24-4, the application of this compound in the production field has become more and more popular.

Reference:
Article; Dressler, Justin J.; Miller, Sarah A.; Meeuwsen, Brian T.; Riel, Asia Marie S.; Dahl, Bart J.; Tetrahedron; vol. 71; 2; (2015); p. 283 – 292;,
Bromide – Wikipedia,
bromide – Wiktionary

Adding a certain compound to certain chemical reactions, such as: 937046-98-5, name is 7-Bromopyrrolo[2,1-f][1,2,4]triazin-4-amine, 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 937046-98-5, Quality Control of 7-Bromopyrrolo[2,1-f][1,2,4]triazin-4-amine

To a dry, argon purged round bottom flask (100 mL) were added 7-bromo- pyrrolo[2, 1 -f] [ 1 ,2,4]triazin-4-ylamine (234 mg, 1.10 mmol) (prepared according to WO2007056170) and anhydrous THF (1.5 mL). TMSCI (276 mu, 2.2 mmol) was then added and the reaction mixture stirred for 2 h. The flask was placed into a dry ice/acetone bath (~ -78 C) and BuLi (2.5 mL, 4.0 mmol, 1.6M in hexanes) was added dropwise. After lh, a solution of If (432.5 mg, 1.0 mmol) in THF was cooled to 0 C and then added to the reaction flask dropwise. After 1 h of stirring at -78 C, the flask was warmed to 0 C and sat. NH4C1 (5 mL) was added to quench the reaction. The organics were extracted using EtOAc (3 10 mL) and the combined organic layers were dried using MgS04. The solvent was removed under reduced pressure and the crude material was purified using flash chromatography (hexanes / EtOAc). 560 mg (90 %) of 2a was isolated as a mixture of two anomers. LC/MS = 567.2 (M + H+). ]H NMR (300 MHz, CDC13): delta 7.85 (m, IH), 7.27 (m, 15H), 7.01 (m, 1H), 6.51 (m, 1H), 4.66 (m, 8H), 4.40 (m, 2H), 3.79 (m, 3H), 1.62 (s, 2′-CH3 from the one anomer), 1.18 (s, 2′-CH3 from the other anomer).

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; CHO, Aesop; CLARKE, Michael, O’neil Hanrahan; WOLCKENHAUER, Scott, Alan; GILEAD SCIENCES, INC.; WO2012/12465; (2012); 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

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

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

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: 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

Synthetic Route of 52723-82-7, These common heterocyclic compound, 52723-82-7, name is 4-Bromo-5-fluoro-2-methylaniline, 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.

A solution of 4-bromo-5-fluoro-2-methylaniline (10.2 g, 50 mmol) and 3- chlorobenzenecarboperoxoic acid (34.5 g, 200 mmol) in DCE (10 mL) was stirred under nitrogen at reflux for 2 hours. After cooling to rt, the mixture was dispersed between DCM and saturated aqueous Na2S03 solution. The organic layer was collected, concentrated to dryness and purified by flash column chromatography to give the title compound as a brown oil (7.02 g, 60.0percent yield).

The synthetic route of 52723-82-7 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; JANSSEN PHARMACEUTICA NV; ARORA, Nidhi; BACANI, Genesis M.; BARBAY, Joseph Kent; BEMBENEK, Scott D.; CAI, Min; CHEN, Wei; DECKHUT, Charlotte Pooley; EDWARDS, James P.; GHOSH, Brahmananda; HAO, Baoyu; KREUTTER, Kevin; LI, Gang; TICHENOR, Mark S.; VENABLE, Jennifer D.; WEI, Jianmei; WIENER, John J. M.; WU, Yao; ZHU, Yaoping; ZHANG, Feihuang; ZHANG, Zheng; XIAO, Kun; (1000 pag.)WO2017/100668; (2017); A1;,
Bromide – Wikipedia,
bromide – Wiktionary

Related Products of 327-52-6, A common heterocyclic compound, 327-52-6, name is 1-Bromo-2,4,5-trifluorobenzene, molecular formula is C6H2BrF3, 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.

[0141] 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 complete, the reactants were maintained at- 20 C for later use.[0142] 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 described above was slowly added dropwise undernitrogen. After 15 min, a solution of the acridine compound as shown in the above reaction formula (2.81 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. The separatedwater layer was extracted with another 50 mL ethyl acetate. The obtained organic layers were collected together andfurther washed with saturated solution of sodium chloride and then dried over anhydrous sodium sulfate, followed byfiltration and concentration to obtain a crude product, which was further treated by column chromatography to obtain acompound (3.69 g, 0.0115 mol, yield 77%).1H NMR (500 MHz, CDCl3) delta 7.05 (d, J = 8.3 Hz, 1 H), 6.91 (d, J = 6.6 Hz, 1 H), 4.56 (d, J = 9.0 Hz, 1H), 4.13?3.96 (m,1 H), 3.68 (d, J = 6.0 Hz, 2H), 2.85?2.65 (m, 2H), 1.86 (dd, J = 12.4, 7.7 Hz, 1H), 1.68 (s, 1H), 1.42 (s, 9H). Ms (M++1): 320.

The synthetic route of 327-52-6 has been constantly updated, and we look forward to future research findings.

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