Month: February 2021

Application of 626-40-4, A common heterocyclic compound, 626-40-4, name is 3,5-Dibromoaniline, molecular formula is C6H5Br2N, 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.

3-Bromo-5-pyrazol-1-yl-phenylamine.To a solution of 3,5-dibromoaniline (0.50 g, 1.99 mmol) in DMSO (2.0 mL) was added sequentially L-Proline (0.041 g, 0.36 mmol), Cs2CO3 (1.16 g, 3.58 mmol), CuI (0.038 g, 0.20 mmol) and pyrazole (0.12 g, 1.80 mmol). The reaction mixture was degassed for 10 min and then heated to 11O0C for 48 h. After the completion of reaction (TLC monitoring), the reaction mixture was cooled to room temperature, added water and extracted with ethyl acetate (x 3). The combined organics was washed with water, dried (Na2SO4), filtered and concentrated. The residue was purified over silica gel (230-400 M, 15% EtOAc-Hexane) to get the desired compound (0.18 g, 37%).

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; PROLYSIS LTD.; WO2007/148093; (2007); A1;,
Bromide – Wikipedia,
bromide – Wiktionary

Adding a certain compound to certain chemical reactions, such as: 4549-33-1, name is 1,9-Dibromononane, 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 4549-33-1, Product Details of 4549-33-1

General procedure: To a stirred solution of n-dibromoalkane (1 equiv.) in anhydrous THF (0.1M) under an argon atmosphere was added tert-BuOK (1.15 equiv.) in portionwise over 30 min. After being stirred under reflux for 16h, the reaction was cooled and subsequently quenched with water. The resulting mixture was then diluted with diethylether, and the layers were separated. The aqueous layer was extracted several times with diethylether, and the combined organic layers were washed with brine, dried over anhydrous Na2SO4, filtered and concentrated under reduced pressure. The resultant crude product was purified by flash column chromatography over silica gel using petroleum ether as eluent to afford the desired product.

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, 1,9-Dibromononane, other downstream synthetic routes, hurry up and to see.

Reference:
Article; Saied, Essa M.; Le, Thuy Linh-Stella; Hornemann; Arenz, Christoph; Bioorganic and Medicinal Chemistry; vol. 26; 14; (2018); p. 4047 – 4057;,
Bromide – Wikipedia,
bromide – Wiktionary

Application of 556-96-7, These common heterocyclic compound, 556-96-7, name is 1-Bromo-3,5-dimethylbenzene, 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.

Magnesium turnings (5.10 g, 210 mmol, 6 equiv) were washed with hexanes and dried in a 120 C oven for 1 h. The vacuum. Upon cooling to room temperature, a small amount of iodine (50 mg) was added to the flask, and the solids were suspended in THF (120 mL). The flask was fitted with a reflux condenser, then vacuum purged/backfilled with nitrogen three times, and warmed to 50 C in an oil bath. A vent needle was added at the top of the reflux condenser to allow rapid gas release during the initiation of Grignard formation. Neat 3,5-dimethylbromobenzene (14.3 mL, 105 mmol, 3 equiv) was then added at a slow dropwise pace. Formation of the Grignard reagent was indicated by the disappearance of the dark brown THF-iodine adduct, at which point the addition was halted until a controlled, gentle reflux was obtained, and the vent needle was removed. Dropwise addition of the bromide was resumed so as to maintain a gentle reflux. After the addition was complete, the solution was stirred at 50 C for 30 mm, then removed from its bath and cooled to 0 C in an ice/water bath. Diethyl phosphite (4.5 mL, 35 mmol, 1 equiv) was added at a fast dropwise pace, and the solution was stirred at 0 C for 1 h. At this time, the reflux condenser was replaced with an addition funnel, and ice cold 6M HC1 (40 mL, prepared by mixing 20 g ice with 20 mL concentrated HC1) was added at a slow dropwise pace. 300 mL water was added and the solution was stirred vigorously for 1 h. The layers were separated and the aqueous phase was thrice extracted with EtOAc. The combined organic layers were washed with brine, dried over Na2SO4 and concentrated. The product was purified by column chromatography (1-3-5% MeOH/DCM). White solid, 7.58 g, 29.3 mmol, 84% yield. NMR spectra were identical to the previously isolated compound.??H NMR (300 MHz, CDC13) oe 7.94 (d, J 477 Hz, 1H), 7.32 (dt, J 1.5, 0.7 Hz, 2H), 7.28 (dt, J= 1.6, 0.7 Hz, 2H),7.17 (tp, J 1.7, 0.8 Hz, 2H), 2.34 (p, J= 0.6 Hz, 12H); 3?P NMR (121 MHz, CDC13) o 22.71.

Statistics shows that 1-Bromo-3,5-dimethylbenzene is playing an increasingly important role. we look forward to future research findings about 556-96-7.

Reference:
Patent; CALIFORNIA INSTITUTE OF TECHNOLOGY; STOLTZ, Brian, M.; WELIN, Eric, R.; VIRGIL, Scott, C.; TADROSS, Pamela; POTOTSCHNIG, Gerit, Maria; NGAMNITHIPORN, Aurapat (Fa); NEGORO, Kenji; LAPOINTE, Guillaume; KLATTE, Max; HALEY, Christopher; GRUENANGER, Christian; GLIBSTRUP, Emil; GILMORE, Christopher; ALLAN, Kevin, McCormack; (114 pag.)WO2019/18539; (2019); 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 25017-13-4 as follows. Formula: C8H8BrF

General procedure: A test tube equipped with a stir bar was charged with (S)-tert-butyl piperidin-3-ylcarbamate (205 mg, 1.02 mmol) and potassium carbonate (281 mg, 2.03 mmol). 1-(2-Bromoethyl)-2-fluorobenzene (170 muL, 1.22 mmol) and acetonitrile (3.0 mL) were added, and the mixture was heated in an 80 C oil bath. After heating overnight (~18 h), the reaction was partitioned between EtOAc and H2O, and the aqueous layer was extracted with EtOAc. The combined organics were concentrated under reduced pressure. The crude material was purified by silica gel chromatography (Rf in 60:40 hexanes:EtOAc = 0.24) to give the product as a colorless, viscous oil that slowly crystallized on standing (238 mg, 72%).

According to the analysis of related databases, 25017-13-4, the application of this compound in the production field has become more and more popular.

Reference:
Article; Hennessy, Edward J.; Saeh, Jamal C.; Sha, Li; MacIntyre, Terry; Wang, Haiyun; Larsen, Nicholas A.; Aquila, Brian M.; Ferguson, Andrew D.; Laing, Naomi M.; Omer, Charles A.; Bioorganic and Medicinal Chemistry Letters; vol. 22; 4; (2012); p. 1690 – 1694;,
Bromide – Wikipedia,
bromide – Wiktionary

Some common heterocyclic compound, 64248-56-2, name is 2-Bromo-1,3-difluorobenzene, molecular formula is C6H3BrF2, 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. Computed Properties of C6H3BrF2

A solution of 2-bromo-1,3-difluorobenzene (25.0 g, 130 mmol) in concentrated H2SO4 (52 mL, 98%) was vigorously stirred at room temperature. Then, concentrated nitric acid (9 mL, 70%) was added dropwise to the solution, and the internal temperature was maintained to be lower than 55C. After the addition, the mixture was further stirred for 30 minutes, and poured on ice. CH2Cl2 (200 mL x 2) was added to the mixture for extraction of the desired compound. The combined organic layer was washed with saturated Na2CO3 and brine, dried over Na2SO4, and concentrated to give 2-bromo-1,3-difluoro-4-nitrobenzene as yellow solid (23.0 g, yield 74%). 1H-NMR Spectrum (300MHz, CDCl3):delta (ppm): 7.10-7.16 (m, 1H), 8.09-8.16 (m, 1H)

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 64248-56-2, its application will become more common.

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

Related Products of 73918-56-6, 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. 73918-56-6 name is 2-(4-Bromophenyl)ethanamine, 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.

Dissolve p-bromophenethylamine (2.0 g, 10 mmol) in a 100 mL round bottom flask under ice bathAfter dissolving 20 mL of dichloromethane, triethylamine (3.0 g, 30 mmol) was added, and then di-tert-butyl dicarbonate (3.3 g) was gradually added dropwise.20 mL of a solution of 15 mmol) of dichloromethane (DCM) was allowed to react at room temperature for 6 hours after the addition. After the reaction is completed, the solvent is distilled off under reduced pressure.40 mL of water was added, and the mixture was extracted with ethyl acetate. Distill the solvent and then silica gel column chromatographyFrom purification, eluent: petroleum ether (PE) / ethyl acetate (EA) = (20:1). A white solid (2.7 g, 90%) was obtained.

At the same time, in my other blogs, there are other synthetic methods of this type of compound, 2-(4-Bromophenyl)ethanamine, and friends who are interested can also refer to it.

Reference:
Patent; Lanzhou University; Zhang Haoli; Zhang Yupeng; Chen Lichuan; Xu Zhuguo; (25 pag.)CN108794490; (2018); A;,
Bromide – Wikipedia,
bromide – Wiktionary

Reference of 626-40-4, These common heterocyclic compound, 626-40-4, name is 3,5-Dibromoaniline, 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.

1000mL 4 neckround bottom flask was charged with 3,5-dibromoaniline (3,5Dibormoaniline)40 g (0.16 mole) and Pd (PPh3)47.4 g (0.006 mole) of potassium carbonate and 88.1 g (0.64 mole) and phenylboronic into the acid 46.6 g (0.0.38 mole), 320mL of toluene put, 160 mL ethanol, 120 mL water was refluxed for 12 hours. To complete the reaction, and the organic layerwas separated and the water layer was extracted twice with 100 mL toluene. Formed organic layer was concentrated underreduced pressure and recrystallized with methanol to intermediate a5(30 g, 76.7%) was obtained.

Statistics shows that 3,5-Dibromoaniline is playing an increasingly important role. we look forward to future research findings about 626-40-4.

Reference:
Patent; SFC CO., LTD.; KIM, JEONG SOO; RYU, YEON KWON; KO, SANG WON; LEE, SU JIN; KIM, JI HWAN; PARK, JIN JOO; (44 pag.)KR2015/129486; (2015); A;,
Bromide – Wikipedia,
bromide – Wiktionary

Related Products of 202865-83-6, The chemical industry reduces the impact on the environment during synthesis 202865-83-6, name is 1-Bromo-3-fluoro-5-methylbenzene, I believe this compound will play a more active role in future production and life.

Compound 22b (50 mg, 177.09 mumol), 1-bromo-3-fluoro-5-methylbenzene (46.87 mg, 247.93 mumol), Pd (OAc) 2 (7.9 mg, 0.035 mmol), BINAP (44 mg, 0.071 mmol) ) And Cs2CO3 (145mg, 0.442mmol) were added in 5mL toluene, heated to 90 under N2 protection for 5h. After the reaction was completed, it was filtered through celite, and the filtrate was spin-dried and separated and purified by a preparative silica gel plate (eluent system B) to obtain compound 22c (10 mg).

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, 1-Bromo-3-fluoro-5-methylbenzene, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; Sichuan Kelun Botai Bio-pharmaceutical Co., Ltd.; Li Guiying; Sun Xiaoyang; You Zejin; Cai Jiaqiang; Wang Lichun; Wang Jingyi; (55 pag.)CN110857298; (2020); A;,
Bromide – Wikipedia,
bromide – Wiktionary

Some common heterocyclic compound, 337915-79-4, name is 5-Bromo-N1-methylbenzene-1,2-diamine, molecular formula is C7H9BrN2, 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. SDS of cas: 337915-79-4

[00320] To a solution of 5-bromo-Nl-methylbenzene-l,2-diamine (7.4 g, 37 mmol) in trimethyl orthoformate (100 mL) was added p-toluenesulfonic acid (0.36g, 1.9 mmol). The reaction mixture was heated at 100 C for 4 h, cooled, concentrated, dissolved in ethyl acetate, washed with brine, dried over sodium sulfate and concentrated. The crude product was used in next step without further purification. (7.3 g, yield 93%) MS (ESI+) e/z: 212.1.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 337915-79-4, its application will become more common.

Reference:
Patent; EPIZYME, INC.; DUNCAN, Kenneth, W.; CHESWORTH, Richard; BORIACK-SJODIN, Paula, Ann; MUNCHHOF, Michael, John; WO2014/100734; (2014); A1;,
Bromide – Wikipedia,
bromide – Wiktionary

Adding a certain compound to certain chemical reactions, such as: 34699-28-0, name is 1-(4-Bromophenyl)-1,2,2-triphenylethylene, 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 34699-28-0, name: 1-(4-Bromophenyl)-1,2,2-triphenylethylene

General procedure: In a 250 mL single-necked flask,Followed by addition of tetramethylene bromide 4 or 6 (1 eq)Diclofenac borate (1 eq or 2 eq),KOAc (4eq or 8eq),PdCl2 (dppf) 2 ¡¤ CH2Cl2 (0.03 eq or 0.06 eq),Treated with 1,4-dioxane,Under nitrogen protection, heated to 80 reaction 24hCooled to room temperature, 1,4-dioxane was removed by distillation,And then extracted with CH2Cl2The solution was washed with water and dried over anhydrous magnesium sulfate.

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; Changzhou University; Wang Yafei; Liao Yuanwei; Zhu Weiguo; (14 pag.)CN106565595; (2017); A;,
Bromide – Wikipedia,
bromide – Wiktionary