Category: bromides-buliding-blocks

Synthetic Route of 112734-22-2, The chemical industry reduces the impact on the environment during synthesis 112734-22-2, name is (4-Bromo-2-fluorophenyl)methanamine, I believe this compound will play a more active role in future production and life.

To a solution of ethyl 2-((2-fluorobenzyl)oxy)-4-formylnicotinate (2.10 g) obtained in Reference Example 183 and (4-bromo-2-fluorophenyl)methanamine (1.48 g) in methanol (13 mL)-THF (13 mL) was added magnesium sulfate (1.67 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, and the filtrate was concentrated. To a solution of the residue in acetic acid (13 mL) was added sodium triacetoxyhydroborate (2.20 g) at room temperature, and the mixture was stirred under a nitrogen atmosphere at room temperature for 3 hr. The reaction mixture 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) to give the title compound (1.06 g). MS: [M+H]+ 445.0 1H NMR (300 MHz, CDCl3) delta 4.32 (2H, s), 4.76 (2H, s), 5.67 (2H, s), 6.93-7.20 (3H, m), 7.22-7.38 (4H, m), 7.71 (1H, t, J = 7.4 Hz), 8.27 (1H, d, J = 5.1 Hz).

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, (4-Bromo-2-fluorophenyl)methanamine, other downstream synthetic routes, hurry up and to see.

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. 49764-63-8, name is 4,5-Dibromobenzene-1,2-diamine, This compound has unique chemical properties. The synthetic route is as follows., Quality Control of 4,5-Dibromobenzene-1,2-diamine

To a Schlenk flask containing a mixed solution of 1,4-dioxane and water (100 mL, 1,4-dioxane/water = 10/1, V/V) under nitrogen, sequentially added4,5-dibromo-o-phenylenediamine(1g, 3.76mmol),4-boronic acid triphenylamine(2.72g, 9.4mmol),K2CO3 (2.08 g, 15.04 mmol) and Pd(PPh3) 4 (87 mg, 0.075 mmol),The mixture was heated with stirring and allowed to react at 90 C overnight. After the reaction is completed, cool to room temperature.The reaction solution was poured into 100 mL of water and extracted with dichloromethane (DCM) (3×100 mL).The organic layer was collected and dried over anhydrous sodium sulfate.(petroleum ether/ethyl acetate, 2/1, V/V) afforded a pale yellow solid.That isN4,N4,N4″,N4″-tetraphenyl[1,1′:2′,1″-terphenyl]-4,4′,4″,5′-tetraamine(The compound of the formula A1 above, 1.79 g, 80%).

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 49764-63-8.

Reference:
Patent; Soochow University (Suzhou); Ran Quan; Zhu Huifang; Fan Jian; (34 pag.)CN109928936; (2019); A;,
Bromide – Wikipedia,
bromide – Wiktionary

Electric Literature of 112734-22-2, The chemical industry reduces the impact on the environment during synthesis 112734-22-2, name is (4-Bromo-2-fluorophenyl)methanamine, I believe this compound will play a more active role in future production and life.

Preparation of 3-[(4-bromo-2-fluorobenzyl)amino]-1-propanesulfonic acid 4-Bromo-2-fluorobenzylamine hydrochloride (5.0 g, 20.8 mmol) was treated with a saturated solution of K2CO3 (80 mL) and EtOAc (3*80 mL) was added. The organic extracts were combined, dried with Na2SO4, filtered, evaporated under reduced pressure and dried in vacuo. To a solution of 4-Bromo-2-fluorobenzylamine (20.8 mmol) in 50% Pinacolone/Toluene (25 mL) was added 1,3-propane sultone solution (2.3 g, 18.9 mmol). The solution was stirred at reflux for 4 hours. The reaction mixture was cooled to room temperature. The solid material was collected by filtration and washed with acetone (2*20 mL). The solid was suspended in EtOH (40 mL). The suspension was stirred at reflux for 1 hour. The mixture was cooled to room temperature, the solid material was collected by filtration, washed with acetone (2*20 mL) and dried in a vacuum oven (50 C.), affording the title compound, 4.42 g (65%). 1H NMR (D2O, 500 MHz) delta ppm 7.35 (m, 2H), 7.26 (t, 2H, J=7.8 Hz), 4.16 (m, 2H), 3.11 (t, 2H, J=7.8 Hz), 2.85 (t, 2H, J=7.6 Hz), 2.00 (m, 2H). 13C (D2O, 125 MHz) delta ppm 161.98, 159.97, 133.37, 128.50, 124.39, 124.31, 119.79, 119.60, 117.32, 117.19, 48.00, 46.15, 44.40, 21.34. 19F (D2O, 282 MHz) delta ppm -114.64. ES-MS 325 (M-1).

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, (4-Bromo-2-fluorophenyl)methanamine, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; Kong, Xianqi; Wu, Xinfu; Bouzide, Abderrahim; Valade, Isabelle; Migneault, David; Bellini, Francesco; US2006/183800; (2006); A1;,
Bromide – Wikipedia,
bromide – Wiktionary

Application of 5279-32-3, 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. 5279-32-3 name is 5,6-Dibromobenzo[d][1,3]dioxole, 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.

Method B: 4-Amino-1-(4-methoxybenzyl)-1H-imidazo[4,5-c]pyridine-2-thiol (100 mg, 0.349 mmol), 5,6-dibromo-1,3-benzodioxole (196 mg, 0.698 mmol), Pd2dba3 (16 mg, 1.8×10-2 mmol), Xantphos (21 mg, 3.5×10-2 mmol), and Cs2CO3 (227 mg, 0.698 mmol) were placed in a vial and degassed dioxane (1.2 mL) was added to the mixture. After heating at 100 C. for 10 h, the mixture was diluted with EA, washed with brine, dried (Na2SO4), filtered, and concentrated in vacuum. The residue was purified by column chromatography (SiO2, MeOH/CH2Cl2, 0 to 10%) to afford the title compound (54 mg, 31%).

At the same time, in my other blogs, there are other synthetic methods of this type of compound, 5,6-Dibromobenzo[d][1,3]dioxole, and friends who are interested can also refer to it.

Reference:
Patent; Myrexis, Inc.; US8017780; (2011); B1;,
Bromide – Wikipedia,
bromide – Wiktionary

Some common heterocyclic compound, 4101-68-2, name is 1,10-Dibromodecan, molecular formula is C10H20Br2, 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: 4101-68-2

Tempo 1 (0.01 mol) was added to a three-neck flask containing 100 ml dry benzene that is maintained at nitrogen atmosphere. To the flask, sodium hydride (0.015 mol) was added and kept refluxed for 24 hrs. The flask was cooled in ice bath and added 1,10- dibromodecane (0.02 mol) in one portion. The refluxing was then resumed for another 72 hrs. The contents of the flask was cooled in ice bath and added 25ml water and transferred to a separatory funnel. The red upper benzene layer was separated , dried over anhydrous magnesium sulfate and solvent removed by rotory evaporation to get a red oil. The oil was purified by column chromatography on silica gel 60. The material was added to the column and eluted first with about 150 ml hexane that removed the excess of dibromodecane. The desired bromodecanoyl ether of Tempol was eluted with a mixture of hexane and ether(90:10). The red eluate was collected and was found to be pure on thin layer chromatography plates developed using the same solvent mixture. The yield was 0.008 mol (80%).The bromoether of Tempol 0.008 mol and triphenyl phosphine (0,01 mol) were taken in a flask and added 20ml of n-propanol. The contents of the flask was kept refluxed under nitrogen for 72 hrs. The flask was cooled and the solvent was removed by rotory evaporation. The residue was dissolved in 10 ml dichloromethane and added to 100 ml ether with stirring. The precipitated product was collected by decantation of the solvent. The residual semisolid was then purified on silica gel 60 column eluting first with dichloromethane and the desired product was ehited with a mixture of dichloromethane and methanol (90:10). Homogeneous fractions combined and solvent removed to get a red-brown semisolid with a yield of 65%. Purity was ascertained by LC-MS (mass =573.4) .

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 4101-68-2, its application will become more common.

Reference:
Patent; COLBY PHARMACEUTICAL COMPANY; MEDICAL COLLEGE OF WISCONSIN, INC.; WO2008/109740; (2008); A2;,
Bromide – Wikipedia,
bromide – Wiktionary

57946-63-1, name is 2-Bromo-4-(trifluoromethyl)aniline, 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. Quality Control of 2-Bromo-4-(trifluoromethyl)aniline

Reference Example 57 4-[2-{[2-Bromo-4-(trifluoromethyl)phenyl]amino}-4-chloro-7-(1-ethylpropyl)-1H-benzimidazol-1-yl]butan-1-ol A mixture of ethyl 4-[2,4-dichloro-7-(1-ethylpropyl)-1H-benzimidazol-1-yl]butanoate (Reference Example 33; 2.24 g, 6.63 mmol), 2-bromo-4-trifluoromethylaniline (3.18 g, 13.25 mmol), p-toluenesulfonic acid monohydrate (1.35 g, 7.09 mmol) and xylene (5.0 mL) was stirred at 130° C. for 15 hr. After cooling, the reaction mixture was neutralized with aqueous saturated sodium hydrogen carbonate and extracted with ethyl acetate (*3). The combined organic layer was washed with brine, dried over anhydrous magnesium sulfate, filtered and concentrated in vacuo. The residue was purified by silica gel column chromatography eluding with a 0-15percent ethyl acetate/n-hexane gradient mixture to give crude ethyl 4-[2-{[2-bromo-4-(trifluoromethyl)phenyl]amino}-4-chloro-7-(1-ethylpropyl)-1H-benzimidazol-1-yl]butanoate. The crude material (MS Calcd.: 573; Found: 574 (M+H)) was subjected for the next step without further purification.

The synthetic route of 57946-63-1 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; TAKEDA PHARMACEUTICAL COMPANY LIMITED; US2009/186879; (2009); A1;,
Bromide – Wikipedia,
bromide – Wiktionary

Related Products of 61326-44-1, 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. 61326-44-1, name is 1,1,2,2-Tetrakis(4-bromophenyl)ethene belongs to bromides-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below.

(1) A mixture of 3,4,2 mg of palladium acetate, 200 g of K2CO3 and 44 mg of tricyclohexylphosphine was added to the reaction tube under N2, followed by addition of 10 mL of DMF and 130 g of 4-vinylpyridine, followed by heating under reflux for 48 h Room temperature. The solvent was removed by rotary evaporator, the product was extracted with CHCl3, washed with water, the organic phase was collected, and dried over anhydrous Mg2SO4. The final organic phase was purified by silica gel column chromatography eluting with CHCl3: MeOH = 30: 1 to give the final product 6.

The synthetic route of 1,1,2,2-Tetrakis(4-bromophenyl)ethene has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Northwest University; Cao Liping; Li Yawen; Dong Yunhong; (17 pag.)CN107141250; (2017); A;,
Bromide – Wikipedia,
bromide – Wiktionary

Application of 460-00-4,Some common heterocyclic compound, 460-00-4, name is 1-Bromo-4-fluorobenzene, molecular formula is C6H4BrF, 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.

Carbazole (5.03 g, 30.1 mmol), 1-Fluoro-4-bromobenzene (14.0 mL, 127 mmol) and Cs2CO3 (39.9 g, 122 mmol) were added to 100 mL of DMF under nitrogen gas, and the mixture was stirred at room temperature for 16 hours. After the reaction mixture was cooled to room temperature and filtered under reduced pressure, the filtrate was washed with distilled water (100 mL X 3) and extracted with EtOAc (100 mL X 3). The organic layer was dried with MgSO 4, filtered under reduced pressure, and the solvent was removed. The reaction mixture was separated by Silica column chromatography (Hexanes ? Hexane: DCM (dichloromethane) = 1: 1) and recrystallized with DCM / MeOH to give 6.42 g (yield: 66%) of pure compound 1-3.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 1-Bromo-4-fluorobenzene, its application will become more common.

Reference:
Patent; LG Display Co., Ltd.; Yoon Dae-w; Seo Bo-min; Ryu Mi-sang; Kim Chun-gi; (39 pag.)KR2019/68072; (2019); A;,
Bromide – Wikipedia,
bromide – Wiktionary

Adding a certain compound to certain chemical reactions, such as: 72678-19-4, name is 2,6-Dibromo-4-(trifluoromethyl)aniline, 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 72678-19-4, Product Details of 72678-19-4

EXAMPLE 4 Synthesis of 2-Amino-4,5-dimethyl-1-(2,6-dibromo-4-trifluoromethylphenyl)pyrrole-3-carbonitrile In 15 ml of toluene, 5.5 g of 4-amino-3,5-dibromobenzotrifluoride, 1.9 g of acetoin, and 34 mg of p-toluenesulfonic acid were dissolved. The reaction solution was heated under reflux for 2.5 hours while conducting azeotropic dehydration. To the reaction mixture, 1.42 g of malononitrile was added. The reaction mixture was heated for 4 hours while being concentrated at 180 C. Water was added to the reaction mixture. The reaction mixture was extracted with chloroform, and subsequently, the extract was dried over anhydrous sodium sulfate. After the desiccant was filtered off, the filtrate was concentrated under reduced pressure. The residue was purified by silica gel column chromatography (eluent:hexane-ethyl acetate=5:1), and was allowed to stand for crystallization to yield 1.2 g of 2-amino-4,5-dimethyl-l-(2,6-dibromo-4-trifluoromethylphenyl)pyrrole-3-carbonitrile. m.p. 158-161 C.

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; Taisho Pharmaceutical Co., Ltd.; US6600038; (2003); 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. 583-75-5, name is 4-Bromo-2-methylaniline, This compound has unique chemical properties. The synthetic route is as follows., Recommanded Product: 4-Bromo-2-methylaniline

Preparation #4: 2-Methyl-4-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-phenylamine A mixture of 4-bromo-2-methylaniline (0.250 g, 1.34 mmol), bis(pinacolato)diboron (0.442 g, 1.747 mmol), dichloro[1,1’bis(diphenylphosphino)-ferrocene]palladium (II) dichloromethane adduct (0.110 g, 0.134 mmol), and potassium acetate (0.329 g, 3.357 mmol) was heated in N,N-dimethylformamide (5 mL) at about 80 C. for about 15 h under an atmosphere of nitrogen. The mixture was allowed to cool to ambient temperature and was purified by flash column chromatography on silica gel using ethyl acetate/heptane (3:7) as the mobile phase to give 2-methyl-4-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-phenylamine as a yellow oil (0.213 g, 0.914 mmol); RP-HPLC (25% to 100% acetonitrile/0.1 M aqueous ammonium acetate, buffered to pH 4.5, over 10 min at 1.0 mL/min; lambda=254 nm; Hypersil C18, 100 A, 5 mum, 250*4.6 mm column) Rt 11.02 min.

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 583-75-5.

Reference:
Patent; Wishart, Neil; Friedman, Michael; Arnold, Lee D.; Yang, Bryant; Fix-Stenzel, Shannon R.; Ericsson, Anna; Michaelides, Michael R.; Qian, Xiao-Dong; Holms, James H.; Steinman, Douglas H.; Tian, Zhengping; Wittenberger, Steven J.; US2006/25383; (2006); A1;,
Bromide – Wikipedia,
bromide – Wiktionary