Bromides-buliding-blocks

28342-75-8,Some common heterocyclic compound, 28342-75-8, name is 1,5-Dibromo-2,4-difluorobenzene, molecular formula is C6H2Br2F2, 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 2-(2-methoxy-1-naphthalenyl)-boronic acid (3.24 g, 16 mmole), 1,5-dibromo-2,4-difluorobenzene (1.78 g, 6.55 mmole), Pd(PPh3)4 (0.33 g, 0.29 mmole) and potassium carbonate (4.53 g, 32.8 mmole) in 1,2-dimethoxyethane (120 ml) and water (30 ml) was stirred with heating at reflux temperature under nitrogen atmosphere for 4 hours. After that reaction mixture cooled down, precipitate collected by filtration to give 1.12 g of the product. Organic phase of the filtrate was evaporated further and the second precipitate collected by filtration, dried in vacuum to give 1.8 g of the product. Crude product as a mixture of diastereomers was used for the next step without further purification. Crude product can be purified by chromatography on silica gel column using gradient elution with mixtures of hexanes and dichlromethane to isolate pure isolated diastereomers. MS: MH+ = 427.1H-NMR of diastereomer 1 (CDCl3, 500 MHz): 3.95 (s, 6H), 7.14 (t, 1H, J = 9 Hz), 7.34-7.37 (m, 3H), 7.38 (d, 2H, J = 9 Hz), 7.43 (td, 2H, J1 = 1 Hz, J2 = 8 Hz), 7.68 (d, 2H, J = 9 Hz), 7.83 (d, 2H, J = 8 Hz), 7.92 (d , 2H, J = 9 Hz).1H-NMR of diastereomer 2 (CDCl3, 500 MHz): 3.91 (s, 6H), 7.14 (t, 1H, J = 9 Hz), 7.31-7.38 (m, 3H), 7.38 (d, 2H, J = 9 Hz), 7.44 (td, 2H, J1 = 1 Hz, J2 = 8 Hz), 7.64 (d, 2H, J = 9 Hz), 7.83 (d, 2H, J = 9 Hz), 7.92 (d, 2H, J = 9 Hz).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 28342-75-8, its application will become more common.

Reference:
Patent; E. I. DU PONT DE NEMOURS AND COMPANY; SKULASON, Hjalti; DIEV, Viacheslav V.; VO, Giang Dong; GAO, Weiying; WU, Weishi; HERRON, Norman; HOWARD, Michael Henry, Jr.; DOGRA, Kalindi; ZOU, Yunlong; (195 pag.)WO2018/97937; (2018); A1;,
Bromide – Wikipedia,
bromide – Wiktionary

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. 583-70-0 name is 2,4-Dimethylbromobenzene, 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. 583-70-0

1-bromo-2,4-dimethylbenzene 12a (1.0 g, 5.40 mmol), bis(pinacolato)diboron (1.90 g, 8.10 mmol),1,1 ‘-bis (diphenylphosphino) ferrocene] dichloropalladium (198 mg, 0.27 mmol) and potassium acetate (1.30 g, 13.5 mmol) was dissolved in 50 mL of ethylene glycol dimethyl ether and heated to reflux for 3 hours. Filtered, and the filtrate was concentrated under reduced pressure. The resulting residue was purified by silica gel column chromatography using eluent system B to give the title product, 2-(2,4-dimethylphenyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane 12b (700 mg, yellow oil), yield: 56.0%.

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

Reference:
Patent; SHANGHAI HENGRUI PHARM CO LTD; JIANGSU HENGRUI MEDICINE CO LTD; Lyu, HEJUN; DONG, QING; FEI, HONGBO; JIANG, HONGJIAN; SONG, PENG; (114 pag.)CN103030646; (2016); B;,
Bromide – Wikipedia,
bromide – Wiktionary

Adding some certain compound to certain chemical reactions, such as: 615-54-3, name is 1,2,4-Tribromobenzene, 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 615-54-3. 615-54-3

Under a nitrogen stream, 16.9 g (0.10 mol) of Exemplified Compound 1-1 was dissolved in 390 m of dehydrated THF, adjusted to -5 C. with an ice-water bath, and 59.4 ml of 1.6M nBuLi (¡Á 0.95 mol ratio to Exemplified Compound 1). -1) was added dropwise for 10 min (the water content of THF was measured by a coulometric titration method and found to be 15 ppm. This corresponds to 3.25 ¡Á 10 -4 mol of water molecules and a corresponding amount of 1.6 M nBuLi solution 0 20 ml was added as a correction amount.) After stirring for 1 hour, 18.6 g of Exemplified Compound 2-7 was added dropwise over 10 min and stirred for 1 hour.During this time, the internal temperature was -10 C to 5 C.480 ml of THF, exemplary compound 4-5A solution prepared by dissolving 9.5 g and 16.8 g of potassium carbonate in 30 ml of pure water was added in this order, and nitrogen bubbling was performed for 20 minutes. To this suspension, 2.7 g of Pd (dba) 2 and 1.8 g of Exemplified Compound 10-1 were added and refluxed for 6 hours. After washing with saturated brine, the solvent was distilled off under reduced pressure. Recrystallization from cyclohexane gave 14.2 g of gray crystals (yield 81%, purity 99.3%).

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 1,2,4-Tribromobenzene.

Reference:
Patent; Konica Minolta Co., Ltd.; Sugita, Shuichi; Okubo, Kimihiko; Nishimura, Hiroshi; Hagiwara, Toshiyuki; (38 pag.)JP2019/99537; (2019); A;,
Bromide – Wikipedia,
bromide – Wiktionary

201138-91-2, 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. 201138-91-2, name is 4,6-Dibromodibenzo[b,d]furan, A new synthetic method of this compound is introduced below.

40.0 g (4-(9-phenyl-9H-carbazole-3-)phenyl) boric acid and 32.6 g 4,6-dibromo-dibenzofuran were added into a 2 L three-neck flask, followed by adding 700 mL toluene and 150 mL ethanol to dissolve. The reaction mixture was aerated with nitrogen gas for 15 minutes, then 150 mL aqueous K2CO3 solution (3.0 eq., 2M) and 2.3 g Pd(PPh3)4 (2 mol %) were sequentially added. The reaction mixture was heated up to 110 C. and reacted overnight. After the reaction finished, the residual was absorbed by the added activated carbon, filtered by suction filtration and removed with solvent by rotary evaporation, followed by drying and recrystallization with a mixture of toluene and ethanol, to produce 48.0 g Intermediate (52) at a yield of 85%.

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; NANJING TOPTO MATERIALS CO.,LTD.; KIM, JIN WOO; QIAN, CHAO; GAO, PENGHUI; WANG, XIAOWEI; (157 pag.)US2018/105534; (2018); A1;,
Bromide – Wikipedia,
bromide – Wiktionary

1435-51-4, Adding a certain compound to certain chemical reactions, such as: 1435-51-4, name is 1,3-Dibromo-5-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 1435-51-4.

j0691j To mixture of 1,3-dibromo-5-fluorobenzene (LXXXVII) (100 g, 393 mmol) and N?,N?-dimethylethane-1,2-diamine (173 g, 1.97 mol, 214 mL) was added t-BuOK (88 g, 787 mmol) in one portion at 25C under N2. The mixture was stirred at 25C for 30 mm, then heated to 110C and stirred for 11.5 h. The mixture was cooled to 25C and concentrated in reduced pressure at 45C. The residue was purified by silica gel chromatography (column height: 250 mm, diameter: 100 mm, 100-200 mesh silica gel, PE/EtOAc = 2:1, Rf = 0.6) to give N?-(3-bromo-5- fluorophenyl)-N2,N2-dimethylethane-1,2-diamine (LXXXVIII) (30 g, 114.9 mmol, 29.2% yield) as a yellow oil. ESIMS found for C,0H,4BrFN2 mlz 261.1 (M+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, 1,3-Dibromo-5-fluorobenzene, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; SAMUMED, LLC; KC, Sunil Kumar; WALLACE, David Mark; CAO, Jianguo; CHIRUTA, Chandramouli; HOOD, John; (274 pag.)WO2017/24021; (2017); A1;,
Bromide – Wikipedia,
bromide – Wiktionary

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

General procedure: Toa solution of 2a (20.0 g, 0.1 mol)and triethylamine (30.3 g, 0.3 mol) in DCM (350 mL) was added ethylchloroformate (12.9 g, 0.1 mol) dropwise at 0 oC and then stirred atroom temperature for 3 h. The reaction mixture was washed with 3M HCl (100 mL¡Á2), dried over Na2SO4 and concentrated under reducedpressure. The residue was purified by silica gel column chromatography (PET/EA= 25:1, v/v) to afford compound 3a as colorless oil (22.3 g, 82.0%).

Statistics shows that 73918-56-6 is playing an increasingly important role. we look forward to future research findings about 2-(4-Bromophenyl)ethanamine.

Reference:
Article; Sun, Zhaozhu; Zhou, Tian; Pan, Xuan; Yang, Ying; Huan, Yi; Xiao, Zhiyan; Shen, Zhufang; Liu, Zhanzhu; Bioorganic and Medicinal Chemistry Letters; vol. 28; 18; (2018); p. 3050 – 3056;,
Bromide – Wikipedia,
bromide – Wiktionary

These common heterocyclic compound, 10016-52-1, name is 2,8-Dibromodibenzo[b,d]furan, 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. 10016-52-1

Example 1.11.15 9-(4′-(8-bromodibenzo[b,d]furan-2-yl)-[1,1′-biphenyl]-4-yl)-9H-carbazole (Compound 15) A mixture of 9-(4′-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-[1,1′-biphenyl]-4-yl)-9H-carbazole (1.75 g, 4.42 mmol), 2,8-dibromodibenzo[b,d]furan (2.52 g, 7.74 mmol), tetrakis(triphenylphosphine) palladium(0) (0.25 g, 0.22 mmol), potassium carbonate (1.83 g, 13.26 mmol), 1,4-dioxane (40.00 mL), and water (8.00 mL) was degassed with bubbling argon for 30 minutes. The reaction mixture was then heated to 80 C. and was stirred overnight (16.5 hours), maintaining an argon atmosphere. Consumption of the starting material was confirmed by thin-layer chromatography and the reaction was cooled to room temperature. The product was extracted with dichloromethane, dried, and purified by silica gel column chromatography with dichloromethane in hexanes as the eluent. The product fractions were then dried and the product was collected to yield Compound 15 (1.09 g, 44%).

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 10016-52-1.

Reference:
Patent; NITTO DENKO CORPORATION; Zheng, Shijun; (40 pag.)US9425408; (2016); B2;,
Bromide – Wikipedia,
bromide – Wiktionary

327-52-6, The chemical industry reduces the impact on the environment during synthesis 327-52-6, name is 1-Bromo-2,4,5-trifluorobenzene, I believe this compound will play a more active role in future production and life.

In a 40 mL vial, a solution of 1-bromo-2,4,5-trifluorobenzene (2.00 g, 9.48 mmol) in DMSO (15 mL) was treated with NaSMe (3.32 g, 47.4 mmol), and the resulting suspension stirred at room temperature for 4 h. The reaction mixture was diluted with DCM, and the organics were washed with water and brine. The volatiles were concentrated to give (2-bromo-4,5-difluorophenyl)(methyl)sulfane (2.20 g, 98%), which was used without further purification in next reaction. 1H NMR (400 MHz, CDCl3) delta 7.23 (dd, J=8.7, 5.7 Hz, 1H), 6.98 (dd, J=8.5, 6.4 Hz, 1H), 2.46 (s, 3H). HPLC: RT=2.756 min; (Chromolith ODS S5 4.6¡Á50 mm (4 min grad) 0-100% B. Flow Rate=4 ml/min. Inj. Vol.=10 uL. Wavelength=220. Oven Temp.=40 C. Solvent A: 10% MeOH -90% H2O-0.1% TFA. Solvent B: 90% MeOH -10% H2O-0.1% TFA).

The chemical industry reduces the impact on the environment during synthesis 1-Bromo-2,4,5-trifluorobenzene. I believe this compound will play a more active role in future production and life.

Reference:
Patent; BRISTOL-MYERS SQUIBB COMPANY; Norris, Derek J.; Delucca, George V.; Gavai, Ashvinikumar V.; Quesnelle, Claude A.; Gill, Patrice; O’Malley, Daniel; Vaccaro, Wayne; Lee, Francis Y.; DeBenedetto, Mikkel V.; Degnan, Andrew P.; Fang, Haiquan; Hill, Matthew D.; Huang, Hong; Schmitz, William D.; Starrett, JR., John E.; Han, Wen-Ching; Tokarski, John S.; Mandal, Sunil Kumar; (220 pag.)US2016/176864; (2016); 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., 937046-98-5

A solution of 7-bromopyrrolo[2,1-f][1,2,4]triazin-4-amine (120 mg, 0.563 mmol) in N,N-dimethylformamide (2.5 mL) was treated with 4-methoxybenzyl chloride (0.168 mL, 1.23 9 mmol), then with cesium carbonate (459 mg, 1.408 mmol), added in one portion. The mixture was stirred at room temperature for 22 h. The mixture was dilutedwith water and extracted twice with ethyl acetate. The combined organic layers were washed with brine, dried over sodium sulfate and concentrated to provide a yellow semisolid. The material was chromatographed on an ISCO Companion 4 g silica gel column and eluted with EtOAc/hexane gradient (5-30%). The product containing fractions werecollected and concentrated to give 7-bromo-N,N-bis(4-methoxybenzyl)pyrrolo[2,1-f] [1,2,4]triazin-4-amine (147.8 mg, 97% purity, 0.316 mmol, 56% yield). Mass spectrum m/z 453, 455 (M+H). ?H NMR (400MHz, chloroform-d) oe 8.14 (s, 1H), 7.23 (d, J=8.6 Hz, 4H), 6.93-6.88 (m, 4H), 6.61 (d, J=1.3 Hz, 2H), 4.94 (s, 4H), 3.83 (s, 6H).

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; BRISTOL-MYERS SQUIBB COMPANY; BHIDE, Rajeev S.; BATT, Douglas G.; CHERNEY, Robert J.; CORNELIUS, Lyndon A.M.; LIU, Qingjie; MARCOUX, David; NEELS, James; POSS, Michael A.; QIN, Lan-ying; RUAN, Zheming; SHI, Qing; SRIVASTAVA, Anurag S.; TINO, Joseph A.; WATTERSON, Scott Hunter; (532 pag.)WO2016/64957; (2016); 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. 327-51-5, name is 1,4-Dibromo-2,5-difluorobenzene, This compound has unique chemical properties. The synthetic route is as follows., 327-51-5

Under a nitrogen atmosphere, 3.0 ml (2.45 mmol) of a THF solution of isopropyl magnesium bromide (manufactured by Tokyo Chemical Industry Co., 0.80 M) and 10 ml of THF were added to a 100 ml Schlenk reaction vessel. At -30 C., 800 mg (2.45 mmol) of 2,3-dibromo-5-hexylthiophene obtained in the step (B) was added dropwise to this mixture. After ripening at the same temperature for 30 minutes, it was cooled to -78 C. and 2.45 ml (2.45 mmol) of a diethyl ether solution of zinc chloride (manufactured by Sigma-Aldrich, 1.0 M) was added dropwise. After gradually raising the temperature to room temperature, the resulting white slurry solution was concentrated under reduced pressure, and 10 ml of a light boiling component was distilled off. 185 mg (0.68 mmol) of 1,4-dibromo-2,5-difluorobenzene (manufactured by Wako Pure Chemical Industries, Ltd.) as a white slurry liquid (3 bromothienyl-2-zinc chloride) obtained and tetrakis Phenylphosphine) palladium (Tokyo Chemical Industry Co., Ltd.) (26.3 mg, 0.023 mmol, 2.3 mol% based on 1,4-dibromo-2,5-difluorobenzene) and 10 ml of THF were added. After conducting the reaction at 60 C. for 15 hours, the reaction vessel was cooled with water and 3 ml of 3N hydrochloric acid was added to terminate the reaction. The mixture was extracted with toluene, and the organic phase was washed with brine and dried over anhydrous sodium sulfate. The residue was purified by silica gel column chromatography (hexane to hexane / dichloromethane = 10/1) and recrystallized from hexane / toluene = 6/4 to obtain 1,4-di (3- Bromo-5-hexylthienyl) -2,5-difluorobenzene (yield 64%) as a brown solid.

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; TOSOH CORPORATION; UEDA, SAORI; HACHIYA, HITOSHI; WATANABE, MAKOTO; (12 pag.)JP2015/227296; (2015); A;,
Bromide – Wikipedia,
bromide – Wiktionary