Category: bromides-buliding-blocks

Application of 656-64-4,Some common heterocyclic compound, 656-64-4, name is 3-Bromo-4-fluoroaniline, molecular formula is C6H5BrFN, 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 3-bromo-4-fluoroaniline ( 1.000 g, 5.263 mmol), methyl 4-(bi momethyl)-3-fluoi benzoate ( 1.430 g, 5.789 mmol) and potassium carbonate ( 1.455 g, 10.525 mmol) in acetonitrile ( 10 mL) was stirred at the room temperature for 15 hr, filtered to remove solids, and concentrated under the reduced pressure to remove the solvents. The residue was chromatographed (Si02, 40 g cartridge; ethyl acetate / hexane = 0 % to 10 %) to give methyl 4-(((3-bromo-4-fluorophenyl)amino)methyl)-3-fluorobenzoate as palw brown oil ( 1.104 g, 58.9 %).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 3-Bromo-4-fluoroaniline, its application will become more common.

Reference:
Patent; CHONG KUN DANG PHARMACEUTICAL CORP.; LEE, Jaekwang; KIM, Yuntae; LEE, Chang Sik; SONG, Hyeseung; GWAK, Dal-Yong; LEE, Jaeyoung; OH, Jung Taek; LEE, Chang Gon; KIM, II Hyang; (1041 pag.)WO2017/23133; (2017); A2;,
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. 39478-78-9, name is 5-Bromo-2-methylaniline, A new synthetic method of this compound is introduced below., HPLC of Formula: C7H8BrN

Example 1; Preparation of (1RS.2SR.6RS.7Sf?)-4-(4′-chloro-4-methylbiphen-3-yl)-10- oxatricyclof5.2.1.02’6ldec-8-ene-3.5-dione.; Step 1 : Preparation of 3-amino-4′-chloro-4-methylbiphenyl.; Tetrakis(triphenylphosphine)palladium (0) (3.7 g, 3 mmol) and 4-chlorophenylboronic acid (20.2 g, 0.13 mol) are added to a solution of 5-bromo-2-methylaniline (20 g, 0.1 mol) in 1 ,2-dimethoxy- ethane (200 ml). After stirring the reaction mixture for 15 minutes at 20 0C, a solution of 20% aqueous sodium carbonate (300 ml) is added to the mixture, and the resulting mixture is refluxed for 24 hours. The reaction mixture is cooled to room temperature, diluted with water (600 ml) and extracted using ethyl acetate. The combined organic extracts are dried over anhydrous sodium sulfate, filtered and the filtrate evaporated under reduced pressure. The residue is further purified by column chromatography on silica gel, eluting with 7% ethyl acetate in hexane to give 3-amino- 4′-chloro-4-methylbiphenyl.

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; SYNGENTA LIMITED; WO2009/19015; (2009); A1;,
Bromide – Wikipedia,
bromide – Wiktionary

Reference of 203302-95-8,Some common heterocyclic compound, 203302-95-8, name is 4-Bromo-3,5-difluoroaniline, molecular formula is C6H4BrF2N, 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 4-bromo-3,5-difluoroaniline (23.0 g, 110 mmol), 4,4,4′,4,,5,5,5′,5′- octamethyl-2,2′-bi(l ,3,2-dioxaborolane) (30.9 g, 122 mmol), dppf (3.0 g, 5.5 mmol), Pd(dppf)Cl2(4.5 g, 5.5 mmol) and KOAc (32.0 g, 331 mmol) in dioxane (230 mL) was heated at 80 C under N2atmosphere for 18 h. The reaction mixture was cooled and filtered. The filtrate was concentrated, and the residue was purified by column chromatography (Si02, petroleum ethenEtOAc = 20: 1) to give the title compound as a light yellow solid. NMR (400 MHz, CDC13): delta 6.13-6.11 (m, 2H), 4.04 (br s, 2H), 1.35 (s, 12H).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 4-Bromo-3,5-difluoroaniline, its application will become more common.

Reference:
Patent; MERCK SHARP & DOHME CORP.; CROWLEY, Brendan; FRALEY, Mark; POTTEIGER, Craig; GILFILLAN, Robert; PATEL, Mehul; ARRINGTON, Ken; MITCHELL, Helen; SCHIRRIPA, Kathy; MCWHERTER, Melody; BIFTU, Tesfaye; NAIR, Anilkumar; WANG, Cheng; YANG, De-Yi; ZHU, Cheng; KAR, Nam Fung; HUANG, Xianhai; CHEN, Lei; ZHOU, Wei; LIU, Qingsheng; CAI, Jiaqiang; WO2015/161011; (2015); A1;,
Bromide – Wikipedia,
bromide – Wiktionary

Synthetic Route of 43204-63-3,Some common heterocyclic compound, 43204-63-3, name is Bis(2-Bromoethyl)amine hydrobromide, molecular formula is C4H10Br3N, 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 35 Preparation of Bis(2-bromoethyl)phosphoramidic dichloride (29) TEA (7.12 g, 70 mmol) was added dropwise to a stirred solution of bis(2-bromoethyl)amine hydrobromide (10.00 g, 32 mmol) and phosphorus oxychloride (4.91 g, 32 mmol) in CH2 Cl2 (50 ml) at 0 C. under N2. The mixture was allowed to stir overnight and then poured over ice. The layers were separated, and the aqueous layer was extracted with CH2 Cl2 (3*50 ml). The organic layers were combined and dried (MgSO4). The filtrate was concentrated under reduced pressure and the residue purified by chromatography (1:4 EtOAc: hexanes) to give 29 as an oil (3.86 g, 35%); 1 H NMR (CDCl3) 3.70 (t, 4H, 6.73 Hz), 3.55 (t, 4H, 6.75 Hz)ppm.

The synthetic route of 43204-63-3 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; University of Rochester; US5233031; (1993); A;,
Bromide – Wikipedia,
bromide – Wiktionary

Adding a certain compound to certain chemical reactions, such as: 1575-37-7, name is 4-Bromobenzene-1,2-diamine, 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 1575-37-7, Application In Synthesis of 4-Bromobenzene-1,2-diamine

Example 248B 5-Bromo-1H-benzotriazole A mixture of Example 248A (262 mg; 1.4 mmol) in 10% H2SO4 (4 mL) was treated with NaNO2 (120 mg; 1.7 mmol) in water (1 mL), stirred for 30 min., diluted with water, and extracted with EtOAc. The extracts were rinsed with brine, dried (Na2SO4), concentrated and purified by flash chromatography (5% MeOH/CH2Cl2) to provide the desired product.

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; Li, Qun; Woods, Keith W.; Zhu, Gui-Dong; Fischer, John P.; Gong, Jianchun; Li, Tongmei; Gandhi, Virajkumar; Thomas, Sheela A.; Packard, Garrick K.; Song, Xiaohong; Abrams, Jason N.; Diebold, Robert B.; Dinges, Jurgen; Hutchins, Charles W.; Stoll, Vincent S.; Rosenberg, Saul H.; Giranda, Vincent L.; US2003/199511; (2003); A1;,
Bromide – Wikipedia,
bromide – Wiktionary

Reference of 112734-22-2, 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. 112734-22-2 name is (4-Bromo-2-fluorophenyl)methanamine, 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.

To a solution of ethyl 2-(2,2-difluoro-2-(pyridin-2-yl)ethoxy)-4-formylnicotinate (1.19 g) obtained in Reference Example 192 and (4-bromo-2-fluorophenyl)methanamine (0.76 g) in methanol (20 mL) was added magnesium sulfate (0.85 g) at room temperature, and the mixture was stirred under a nitrogen atmosphere at room temperature for 1 hr. The insoluble material was filtered off, to the filtrate were added acetic acid (2 mL) solution and sodium triacetoxyhydroborate (1.13 g) at room temperature, and the mixture was stirred under a nitrogen atmosphere at room temperature overnight. The reaction mixture was concentrated, the residue was diluted with saturated aqueous sodium hydrogen carbonate solution and ethyl acetate, and the organic layer was separated, washed with saturated brine, dried over anhydrous magnesium sulfate and concentrated. The residue was purified by silica gel chromatography (hexane-ethyl acetate), and the obtained solid was washed with diisopropyl ether to give the title compound (0.42 g). MS: [M+H]+ 478.0

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

Reference:
Patent; Takeda Pharmaceutical Company Limited; SUGIMOTO, Takahiro; NAKAMURA, Minoru; SAKAMOTO, Hiroki; SUZUKI, Shinkichi; YAMADA, Masami; KAMATA, Makoto; KOJIMA, Takuto; FUJIMORI, Ikuo; SHIMOKAWA, Kenichiro; EP2921480; (2015); 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. 1647-26-3, name is 1-Bromo-2-cyclohexylethane, This compound has unique chemical properties. The synthetic route is as follows., HPLC of Formula: C8H15Br

General procedure: To a solution ofsodium 4-hydroxynaphthalene-1-sulfonate (2.0 g, 8.12 mmol) inethanol (6 mL) was added water (6 mL), sodium hydroxide (813 mg,20.31 mmol) and bromoethane (1.33 g, 12.18 mmol). The mixture wasstirred at 80 C overnight in a seal tube. The mixture was cooled andwhite solid precipitated. The resulting precipitated solid was filteredand the filtercake was washed with dichloromethane to give 10a as awhite solid. (1.92 g, yield 86.2%).

According to the analysis of related databases, 1647-26-3, the application of this compound in the production field has become more and more popular.

Reference:
Article; He, Yulong; Dou, Huixia; Gao, Dingding; Wang, Ting; Zhang, Mingming; Wang, Heyao; Li, Yingxia; Bioorganic and Medicinal Chemistry; vol. 27; 19; (2019);,
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. 452-62-0, name is 3-Bromo-4-fluorotoluene, A new synthetic method of this compound is introduced below., SDS of cas: 452-62-0

14a. (2-Fluoro-5methylphenyl)(6-(4-methylthiophenyl)(2H-benzo(d)1,3-dioxolen-5-yl))methan-1-ol To a solution of 3-bromo-4-fluorotoluene (0.7 mL, 5 mmol) in anhydrous THF (25 mL) at -78 C. under nitrogen atmosphere, a solution of t-BuLi in pentane (5.9 mL, 10 mmol) was added and the mixture stirred for 15 minutes. (color change observed). To this reaction mixture the product of Example 1b (1.34 g, 5 mmol), dissolved in anhydrous THF (20 mL), was added drop-wise and stirred at -78 C. for 15 minutes, then slowly allowed to warm to room temperature and stirred for 3 hours at room temperature. The reaction was then quenched with saturated aqueous ammonium chloride and the organic layer was separated. The organic layer was washed with brine, dried over anhydrous sodium sulfate, filtered and the filtrate was evaported under reduced pressure. Purification by flash column chromatography using 5% ethyl acetate in hexanes as the eluant gave the title compound as a white solid, (1.42 g, 74% yield), mp 110 C. 1H NMR (CDCl3, 300 MHz) delta 7.26-7.18 (m, 5H), 7.01-6.98 (m, 1H), 6.87 (s, 1H), 6.82-6.76 (s, 1H), 6.69 (s, 1H), 5.97 (s, 1H), 5.95 (s, 2H), 2.50 (s, 3H), 2.31 (s, 3H), 2.10 (s, 1H). 13C NMR (CDCl3, 75.45 MHz) delta 159.5, 156.3, 147.1, 146.8, 137.4, 137.3, 135.0, 133.4, 133.4, 130.2, 129.8, 129.3, 129.2, 128.0, 127.9, 126.2, 115.0, 114.8, 110.0, 107.5, 101.2, 67.2, 20.8, 15.8. LRMS (APIMS) m/z 782 (2M+NH4)+, 365 (M-OH)+.

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; Khanapure, Subhash P.; Garvey, David S.; Earl, Richard A.; Ezawa, Maiko; Fang, Xinqin; Gaston, Ricky D.; US2002/119977; (2002); 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. 2924-09-6, name is 5-Bromo-2-fluoroaniline, A new synthetic method of this compound is introduced below., HPLC of Formula: C6H5BrFN

To a solution of 5-bromo-2-fluoroaniline (1 g, 5.26 mmol) in L/,L/?-dimethylformamide (10 ml), potassium iodide (2.18 g, 13.1 mmol), and sodium carbonate (1 .95 g, 18.4 mmol) were added and the reaction mixture was heated to 150 C. Then 1 -bromo-2-(2-bromoethoxy)ethane (1.34 g, 5.77 mmol) was added and heating was continued for 16 h. After completion of the reaction (monitored by TLC), the reaction mixture was diluted with water (25 mL) and extracted with ethyl acetate (2 x 15 mL). The combined organic extracts were dried over Na2S04, filtered and concentrated under reduced pressure to yield the crude product. The crude material was purified by flash column chromatography using hexane/ ethyl acetate (80:20) to afford the title compound (0.8 g, 58%).1H-NMR (400 MHz, CDCI3) d = 7.03-7.04 (m, 2H), 6.90-6.92 (m, 1 H), 3.87-3.88 (m, 4H), 3.08-3.10 (m, 4H).

The synthetic route of 2924-09-6 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; AC IMMUNE SA; NAMPALLY, Sreenivasachary; GABELLIERI, Emanuele; MOLETTE, Jerome; (0 pag.)WO2019/233883; (2019); A1;,
Bromide – Wikipedia,
bromide – Wiktionary

Related Products of 76153-06-5, A common heterocyclic compound, 76153-06-5, name is 5-Bromo-3-methylbenzene-1,2-diamine, molecular formula is C7H9BrN2, 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.

Isothiocyanatomethane (0.055 g, 0.746 mmol) in N,N-dimethylformamide (1.0 mL) was added dropwise slowly to a stirred solution of 5-bromo-3-methylbenzene-l,2-diamine (0.150 g, 0.746 mmol) in N,N-dimethylformamide (1.5 mL) at 0 0C. The cold bath was removed, the reaction mixture was capped and stirred at room temperature for 48 h. N-(3-Dimethylaminopropyl)-N’-ethylcarbodiimide hydrochloride (0.157 g, 0.821 mmol) was added and the reaction mixture capped and heated at 40 0C overnight. The resulting mixture was diluted with methanol, filtered and purified using reverse-phase preparatory HPLC (10-50 % acetonitrile + 0.1 % TFA in H2O + 0.1 % TFA, over 30 min). Fractions containing the desired product were combined and most of the solvent removed under reduced pressure. Acetonitrile was added and the resulting mixture loaded on a Strata ion exchange column. The column was washed successively with water, acetonitrile, methanol and 5 % ammonium hydroxide in methanol. The product eluted with the 5% ammonium hydroxide in methanol and was concentrated under reduced pressure and dried under high vacuum to give the desired product (0.128 g, 0.53 mmol, 72 % yield) as a slightly yellow waxy solid. MS (ESI) m/z 240 [M]+, 242 [M+2]+.

The synthetic route of 76153-06-5 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; SIGNAL PHARMACEUTICALS, LLC; ELSNER, Jan; HARRIS, Roy, L.; LEE, Branden; MORTENSEN, Deborah; PACKARD, Garrick; PAPA, Patrick; PERRIN-NINKOVIC, Sophie; RIGGS, Jennifer; SANKAR, Sabita; SAPIENZA, John; SHEVLIN, Graziella; TEHRANI, Lida; XU, Weiming; ZHAO, Jingjing; PARNES, Jason; MADAKAMUTIL Loui; FULTZ Kimberly; NARLA, Rama K.; WO2010/62571; (2010); A1;,
Bromide – Wikipedia,
bromide – Wiktionary