Tag: M.W=200-300

Reference of 22364-25-6,Some common heterocyclic compound, 22364-25-6, name is 4-Bromo-2,3-dimethylaniline, molecular formula is C8H10BrN, 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.

EXAMPLE 26 Preparation of 2,3-Dimethyl-4-methylthiobromobenzene 603 g (5.85 mol) of tert-butyl nitrite and 375 g of copper powder (5.9 mol) are initially charged in 3000 ml of dimethyl disulfide, and 761 g (3.75 mol) of 4-bromo-2,3-dimethylaniline are added dropwise at from 50 to 58 C. The mixture is subsequently stirred at from 75 to 80 C. for 9 hours. For work-up, the mixture is cooled, the residue is filtered off and the filtrate is washed with saturated aqueous NaHCO3 solution. For purification of the product, the organic phase is separated by distillation. Initially, the excess dimethyl disulfide is separated off at atmospheric pressure. 1870 g of dimethyl disulfide (purity>97% according to GC) are recovered. The residue is subsequently subjected to fractional distillation under reduced pressure (0.1 mbar). Yield: 523 g (60%), purity according to GC 99%.

The synthetic route of 22364-25-6 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; BASF Aktiengesellschaft; US6469176; (2002); B1;,
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. 28342-75-8, name is 1,5-Dibromo-2,4-difluorobenzene, This compound has unique chemical properties. The synthetic route is as follows., Computed Properties of C6H2Br2F2

Step 1: Synthesis of (3aR,5R,7aS)-5-[(benzyloxy)methyl]-7a-(5-bromo-2,4-difluorophenyl)hexahydro-1H-pyrano[3,4-c][1,2]oxazole (C6) P1 (4.01 g, 16.5 mmol) was added to a three neck round-bottomed flask (oven dried) equipped with a thermocouple, a nitrogen inlet and mechanical overhead stirrer. Toluene:isopropyl ether (1:1, 160 mL) was added and the resulting solution was cooled to -74¡ã C. Boron trifluoride-diethyl etherate (46.5percent, 4.91 ml, 18.5 mmol) was added and the resulting solution was allowed to stir at -74¡ã C. for 30 minutes. 2,4-Difluoro-1,5-di-bromobenzene (5.01 g, 18.4 mmol) was added followed by a slow addition of n-butyllithium (2.5 M in hexanes, 6.96 mL, 17.4 mmol) ensuring the internal temperature did not rise >5¡ã C. The resulting solution was allowed to stir at -78¡ã C. for 90 minutes. Saturated aqueous ammonium chloride (100 mL) was added and the resulting mixture was allowed to warm to room temperature, at which point it was partitioned between ethyl acetate (1*200 mL) and water (1*600 mL). The organic layer was extracted and the aqueous was back extracted with ethyl acetate (3*200 mL). The combined organics were washed with brine (1*100 mL) and the organic layer was dried over sodium sulfate, filtered, and the filtrate concentrated in vacuo Silica gel chromatography (Gradient 10percent to 70percent ethyl acetate in heptane) provided the product as a clear oily residue. Yield: 3.11 g, 7.06 mmol, 43percent. 1H NMR (400 MHz, CD3OD), delta 8.09 (t, J=8.3 Hz, 1H), 7.31-7.36 (m, 4H), 7.25-7.29 (m, 1H), 7.12 (dd, J=11.5, 8.4 Hz, 1H), 4.55 (s, 2H), 4.06 (dd, J=12.6, 1.7 Hz, 1H), 3.78 (d, J=12.5 Hz, 1H), 3.73-3.8 (m, 1H), 3.69 (d, J=7.2 Hz, 1H), 3.53-3.57 (m, 2H), 3.49 (dd, J=7.3, 5.2 Hz, 1H), 3.05-3.11 (m, 1H), 1.82-1.87 (m, 1H), 1.52-1.61 (m, 1H).

According to the analysis of related databases, 28342-75-8, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Pfizer Inc.; Brodney, Michael Aaron; Beck, Elizabeth Mary; Butler, Christopher Ryan; Davoren, Jennifer Elizabeth; O’Neill, Brian Thomas; US2014/163015; (2014); A1;,
Bromide – Wikipedia,
bromide – Wiktionary

Reference of 73918-56-6, These common heterocyclic compound, 73918-56-6, name is 2-(4-Bromophenyl)ethanamine, 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: The appropriate aldehyde 6a-c and 12a-g (1 mmol) was dissolved in 5 mL of CH2Cl2 in a round bottom flask. Then AcOH (1 mmol) and the appropriate amine (1.1 mmol) were added to the stirring solution at room temperature. The mixture was allowed to stir at room temperature for 20 min before NaBH(AcO)3 (3 mmol) was added. The mixture was allowed to stir at room temperature for overnight. Then,after completion, the reaction was quenched with NaOH 1M solution(15 mL). The mixture was then allowed to stir for 30 min. The reaction mixture was then diluted with EtOAc (10 mL), washed two times with EtOAc (10 mL) and once with brine (20 mL). The organic extracts were collected and then dried over Na2SO4, and the solvent was evaporated to yield the crude compounds 7a-e, 13a-o, 14a-b and 15a which were purified by silica gel column chromatography.

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

Reference:
Article; Liu, Pingxian; Yang, Yang; Ju, Yuan; Tang, Yunxiang; Sang, Zitai; Chen, Lijuan; Yang, Tao; An, Qi; Zhang, Tianyu; Luo, Youfu; Bioorganic Chemistry; vol. 80; (2018); p. 422 – 432;,
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. 33070-32-5, name is 5-Bromo-2,2-difluorobenzodioxole, This compound has unique chemical properties. The synthetic route is as follows., Quality Control of 5-Bromo-2,2-difluorobenzodioxole

General procedure: Method A. A solution of Pd(OAc)2 (25.2 mg, 0.112 mmol) and triphenylphosphine (147 mg, 0.560 mmol) in absolute ethanol (4 mL) and anhydrous toluene (4 mL) was stirred at RT under nitrogen for 10 min. After that period, commercially available 5-chloro-2-nitrotoluene 4 (646 mg, 3.76 mmol), 4 mL of 2M aqueous Na2CO3, and the appropriate boronic acid R1B(OH)2 (6.03 mmol) were sequentially added. The resulting mixture was heated at 100 C in a sealed vial under nitrogen overnight. After being cooled to RT, the mixture was diluted with water and extracted with EtOAc. The combined organic phase were dried and concentrated. The crude product was purified by flash chromatography over silica gel column using n-Hex/EtOAc or CHCl3/MeOH mixtures as the eluent.

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 33070-32-5.

Reference:
Article; Granchi, Carlotta; Roy, Sarabindu; De Simone, Alessio; Salvetti, Irene; Tuccinardi, Tiziano; Martinelli, Adriano; MacChia, Marco; Lanza, Mario; Betti, Laura; Giannaccini, Gino; Lucacchini, Antonio; Giovannetti, Elisa; Sciarrillo, Rocco; Peters, Godefridus J.; Minutolo, Filippo; European Journal of Medicinal Chemistry; vol. 46; 11; (2011); p. 5398 – 5407;,
Bromide – Wikipedia,
bromide – Wiktionary

Application of 1435-51-4, 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. 1435-51-4 name is 1,3-Dibromo-5-fluorobenzene, 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.

Example 14 3-Bromo-5-fluorobenzonitrile A 250-mL round-bottom flask equipped with a magnetic stir bar was charged with 1,3-dibromo-5-fluorobenzene (7.70 g, 30.3 mmol), DMF (45 mL), pyridine (4.9 mL), and copper (I) cyanide (2.72 g, 30.3 mmol) under nitrogen. A reflux condenser was attached to the flask. The green, cloudy mixture was stirred at reflux for 3 h. Once lower Rf impurities were observed, the reaction was allowed to cool to room temperature. The reaction was quenched with 30 mL of ether, and a precipitate formed in the dark solution. The precipitate was gravity-filtered though Celite. The filtrate was rinsed three times with ether (100 mL/50 g bromide). The isolated solution was added to a separatory funnel. The organic layer was washed with a 2:1 mixture of water and concentrated ammonium hydroxide (30 mL), followed by saturated ammonium chloride solution (2*30 mL) and saturated sodium bicarbonate (30 mL). The aqueous layers were extracted with ether (3*40 mL). The organic layers were combined and dried over anhydrous sodium sulfate. The product was purified by flash column chomatography to yield 3-bromo-5-fluorobenzonitrile (2.10 g, 35%). 1H NMR (400 MHz, CDCl3) delta 7.62 (s, 1H), 7.54-7.50 (m, 1H), 7.35-7.32 (m, 1H).

At the same time, in my other blogs, there are other synthetic methods of this type of compound, 1,3-Dibromo-5-fluorobenzene, and friends who are interested can also refer to it.

Reference:
Patent; Glaxo Group Limited; US2009/203657; (2009); A1;,
Bromide – Wikipedia,
bromide – Wiktionary

These common heterocyclic compound, 327-51-5, name is 1,4-Dibromo-2,5-difluorobenzene, 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. category: bromides-buliding-blocks

Add 1,4-dibromo-2,5-difluorobenzene (1.09 g, 4 mmol), phenylboronic acid (1.21 g, 10 mmol), tetrakis(triphenylphosphine)palladium(0) (468 mg, 0.4 mmol) THF (50 mL) and aqueous potassium carbonate (1M, 20 mL) were then evaporated and then th After cooling to room temperature, the layers were separated. The aqueous phase was extracted with dichloromethane (3¡Á50 mL). The residue was purified by silica gel column was using dichloromethane: hexane (1: 5) as eluent to give the product as a white solid (0.82g, 77.1%);

The synthetic route of 1,4-Dibromo-2,5-difluorobenzene has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Shandong Normal University; Ren Xiuhui; Zhu Fucheng; Zhang Xi; Geng Yan; (23 pag.)CN110003179; (2019); A;,
Bromide – Wikipedia,
bromide – Wiktionary

Some common heterocyclic compound, 327-51-5, name is 1,4-Dibromo-2,5-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. Application In Synthesis of 1,4-Dibromo-2,5-difluorobenzene

1,4-Dibromo-2,5-difluorobenzene (51.2 g, 188 mmol) was dissolved in 1,2-diethoxyethane (400 ml), and a 2.5 M n-butyllithium/ hexane solution (76.0 ml, 190 mmol) was slowly added dropwise thereto at -78 C. in the presence of nitrogen gas. [0674] After the reaction solution was stirred at -78 C. for 30 minutes, dry ice was added thereto, followed by stirring for further 30 minutes. After the temperature was gradually raised to room temperature, water (200 ml) was added to the reaction liquid. The reaction liquid was diluted with ethyl acetate, and washed with a 10% aqueous sodium carbonate solution (200 ml¡Á2). Then, the obtained aqueous layers were combined, and made acidic by adjustment with 1 N hydrochloric acid. The precipitated yellow solid was filtered and dried to obtain the title compound (30.0 g, 67%). [0675] 1H NMR (DMSO-d6, 400 MHz): delta 7.90-7.87 (m, 1H), 7.79-7.75 (m, 1H).; MS (ESI) m/z 191 (M+H-44)+

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 327-51-5, its application will become more common.

Reference:
Patent; AJINOMOTO CO., LTD.; Ueno, Hirokazu; Yamamoto, Takashi; Takashita, Ryuta; Yokoyama, Ryohei; Sugiura, Toshihiko; Kageyama, Shunsuke; Ando, Ayatoshi; Eda, Hiroyuki; Eviryanti, Agung; Miyazawa, Tomoko; Kirihara, Aya; Tanabe, Itsuya; Nakamura, Tarou; Noguchi, Misato; Shuto, Manami; Sugiki, Masayuki; Dohi, Mizuki; US2015/51395; (2015); A1;,
Bromide – Wikipedia,
bromide – Wiktionary

1193389-40-0, name is 1-(4-Bromophenyl)cyclobutanamine hydrochloride, 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. Recommanded Product: 1193389-40-0

Intermediate AN-(1-(4-bromophenyl)cyclobutyl)-4-(difluoromethoxy)benzenesulfonamideTo a solution of 1-(4-bromophenyl)cyclobutanamine, HCl (845 mg, 3.22 mmol) in DMF (10 mL), was added diisopropylethylamine (1.69 mL, 9.66 mmol) and 4-(difluoromethoxy)benzene-1-sulfonyl chloride (0.529 mL, 3.22 mmol). The reaction mixture was then stirred at r.t., overnight. This mixture was then used, as is, in the following experiment.

The synthetic route of 1193389-40-0 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Bristol-Myers Squibb Company; US2011/207749; (2011); A1;,
Bromide – Wikipedia,
bromide – Wiktionary

Adding a certain compound to certain chemical reactions, such as: 154264-95-6, name is 7-Bromo-4-methyl-3,4-dihydro-2H-benzo[b][1,4]oxazine, 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 154264-95-6, COA of Formula: C9H10BrNO

n-BuLi (5.79 ml, 14.47 mmol) was added to a stirred, cooled -78 C solution of 7-bromo-4-methyl-3,4-dihydro-2H-l,4-benzoxazine (Int-81a, 3 g, 13.15 mmol) in THF (24 ml). After stirring lh at -78 C for 1 hour., DMF (2.037 ml, 26.3 mmol) was added dropwise and the mixture allowed to warm slowly over 2 hours to room temperature. The reaction was quenched with aqueous ammonium chloride, and the product extracted into ethyl acetate. The organic phase was washed with brine, dried (NaiSC ), filtered and under reduced pressure to provide Int-81b (2.32 g, 13.09 mmol, 100 % yield) as a green 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; MERCK SHARP & DOHME CORP.; KOZLOWSKI, Joseph A.; ROSENBLUM, Stuart B.; COBURN, Craig A.; SHANKAR, Bandarpalle, B.; ANILKUMAR, G., Nair; CHEN, Lei; DWYER, Michael, P.; JIANG, Yueheng; KEERTIKAR, Kartik, M.; LAVEY, Brian, J.; SELYUTIN, Oleg, B.; TONG, Ling; WONG, Michael; YANG, De-Yi; YU, Wensheng; ZHOU, Guowei; WU, Hao; HU, Bin; ZHONG, Bin; SUN, Fei; JI, Tao; SHEN, Changmao; RIZVI, Razia; ZENG, Qingbei; WO2012/41014; (2012); A1;,
Bromide – Wikipedia,
bromide – Wiktionary

Reference of 69321-60-4, 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. 69321-60-4, name is 2,6-Dibromotoluene, This compound has unique chemical properties. The synthetic route is as follows.

A mixture of 1,3-dibromo-2-methylbenzene (Combi Blocks catOT-1437: 339 mg, 1.356 mmol), tert-butyl 2-(2-methyl-3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)-4,6-dihydro-5H-pyrrolo[3,4-d]thiazole-5-carboxylate (200.0 mg, 0.452 mmol), sodium carbonate (96 mg, 0.904 mmol) and tetrakis(triphenylphosphine)palladium(0) (52.2 mg, 0.045 mmol) in dioxane (3.00 mL)/ water (1.0 mL) was heated at 90 C. overnight. The reaction was then cooled to room temperature, diluted with saturated aqueous NH4Cl, and extracted with EtOAc (3¡Á30 mL). The combined organic layers were washed with brine, dried over Na2SO4, filtered, and the filtrate was concentrated under reduced pressure. The crude residue was purified by chromatography on silica gel, eluting with 0-40% EtOAc/hexanes, to give the desired product (210 mg). LC-MS calculated for C24H26BrN2O2S (M+H)+: m/z=485.1/487.1; found 485.0/487.0.

The chemical industry reduces the impact on the environment during synthesis 2,6-Dibromotoluene. I believe this compound will play a more active role in future production and life.

Reference:
Patent; Incyte Corporation; Wu, Liangxing; Qian, Ding-Quan; Lu, Liang; Lajkiewicz, Neil; Konkol, Leah C.; Li, Zhenwu; Zhang, Fenglei; Li, Jingwei; Wang, Haisheng; Xu, Meizhong; Xiao, Kaijiong; Yao, Wenqing; (101 pag.)US2018/177784; (2018); A1;,
Bromide – Wikipedia,
bromide – Wiktionary