Category: 65896-11-9

Some common heterocyclic compound, 65896-11-9, name is 2-Bromo-6-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. name: 2-Bromo-6-fluoroaniline

At 15 deg.C, 2-bromo-6-fluoroaniline (1.00 g, 5.26 mmol) and dimethylphosphine oxide (451.84 mg, 5.79 mmol) in water (20ml) mixture was added potassium carbonate ( 2.91 g, 21.05 mmol) and Pd / C (150 mg). The reaction mixture was stirred at 160 deg.C microwave heating for 3 hours. TLC (petroleum ether: ethyl acetate = 10: 1) showed the reaction was complete. The reaction mixture (20mL × 4) and extracted with dichloromethane. The combined organic layer was filtered, the filtrate was concentrated and purified by column chromatography (dichloromethane: methanol = 1: 0-10: 1) afforded the title compound (100mg, yield 10.16%) as a yellow solid.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 65896-11-9, its application will become more common.

Reference:
Patent; Nanjing Mingde New Drug Research and Development Co. Ltd.; Qilu Pharmaceutical Co., Ltd.; Ding, Zhaozhong; Zhang, Minghui; Chen, Shuhui; Liu, Xile; Zhu, Yidong; Fan, Chuanwen; Zhao, Baoping; Zhang, Long; Chen, Dong; Yang, Yingying; Zheng, Qingmei; Zheng, Shansong; Wan, Haiwen; Hu, Jinqing; (93 pag.)CN105330698; (2016); A;,
Bromide – Wikipedia,
bromide – Wiktionary

65896-11-9, name is 2-Bromo-6-fluoroaniline, 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-6-fluoroaniline

N-(2-Bromo-6-fluorophenyl)pivalamide. 2-Bromo-6-fluoroaniline (43.2 mmol, 8.2 g) was dissolved in pyridine (124 mmol, 10 mL). Pivaloyl chloride (57.15 mmol, 7.0 mL) was added to the mixture. Reaction was stirred at room temperature for 3 hours. Reaction mixture was concentrated in vacuo. Residue was treated with ethyl acetate (50 mL). Mixture was washed 2×1N HCl, 1× brine. Organic layer was dried (magnesium sulfate), filtered and concentrated in vacuo. Residue was treated with hexanes and triturated. Resulting solids were filtered off, washed with hexanes then dried in vacuo. Title compound was obtained as white solid in 76% yield. 1H NMR (300 MHz, CDCl3): delta=7.39-7.31 (m, 1H), 7.14-7.03 (m, 2H), 6.98 (bs, 1H), 1.34 (s, 9H). MS m/e (M+H)+=274.1, 276.1.

The synthetic route of 65896-11-9 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Bristol-Myers Squibb Company; US2007/49577; (2007); 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. 65896-11-9, name is 2-Bromo-6-fluoroaniline, This compound has unique chemical properties. The synthetic route is as follows., Safety of 2-Bromo-6-fluoroaniline

General procedure: To a solution of o-haloaniline (4.63 mmol) in dry DCM (20 mL) at room temperature was dropped acyl chloride (5.09 mmol). The reaction mixture was stirred for 24 hours then poured into water, extracted with DCM, washed with saturated NaHCO3, brine, dried over MgSO4, filtered and concentrated. The product was carried on to next step without any further purification in most cases.

According to the analysis of related databases, 65896-11-9, the application of this compound in the production field has become more and more popular.

Reference:
Article; Shi, Yajie; Zhou, Qifan; Du, Fangyu; Fu, Yang; Du, Yang; Fang, Ting; Chen, Guoliang; Tetrahedron Letters; vol. 60; 40; (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. 65896-11-9, name is 2-Bromo-6-fluoroaniline, A new synthetic method of this compound is introduced below., Application In Synthesis of 2-Bromo-6-fluoroaniline

Preparation of intermediate 3A:N-(4-bromophenyl)-4-fluorobenzothiazol-2-ylamine2-Bromo-6-fluoroaniline (500 mg, 2.63 mmol) and potassium carbonate (5726 mg, 5.26 mmol) were placed in a flask, to which was added 10 mL of DMSO. l-Bromo-4-thiocyanato-benzene (845 mg, 3.95 mmol) was added under nitrogen protection and resulting mixture was stirred at room temperature for 30 min. Cuprous iodide (50 mg, 0.263 mmol) was added and then heated to 120 C under nitrogen protection, and reacted overnight. The mixture was cooled to room temperature, poured into water to give a precipitate, which was filtered to give 383 mg of compound 3 A, which was used directly in the next step without further purification. Yield: 45.2%.MS (ESI, m/z): [M+H]+: 324.0

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; BEIJING HANMI PHARMACEUTICAL CO., LTD; ZHANG, Bo; YANG, Jun; LIU, Jinming; HUANG, Hai; WU, Yong; TAO, Ran; XU, Jiangcheng; SHEN, Ning; MOON, Sunghwan; KIM, Maengsup; WO2013/56679; (2013); A1;,
Bromide – Wikipedia,
bromide – Wiktionary

Reference of 65896-11-9, 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 65896-11-9 as follows.

To a solution of 2-(l-(((9Eta-fluoren-9-yl)methoxy)carbonyl)-4-(ter£- butoxycarbonyl)piperazin-2-yl)acetic acid (5 g, 10.72 mmol) in dichloromethane (100 mL) with Lambda/,Lambda/-dimethylformamide (2 drops) was added oxalyl dichloride (3.4 g, 26.8 mmol). The reaction mixture was stirred at room temperature for 1 hour, then concentrated. Tetrahydrofuran (100 mL) was added to the concentrate followed by the slow addition of a solution containing 2-bromo-6-fluoroanaline (3 g, 16 mmol) and diisopropylethylamine (9 mL) in tetrahydrofuran (20 mL). The solution was stirred at room temperature for 2 hours before the addition of piperazine (2.77 g, 32.2 mmol) after which the solution was stirred for 15 hours. The reaction mixture was concentrated onto silica gel and purified via flash chromatography (0-100 % ethyl acetate/hexane, then 0-10 % methanol/dichloromethane) to afford the title compound. 1H NMR (300 MHz, DMSO-J6) delta ppm 7.47 – 7.65 (m, 1 H) 7.21 – 7.46 (m, 2 H) 3.55 – 4.05 (m, 2 H) 2.67 – 3.14 (m, 3 H) 2.49 – 2.67 (m, 2 H) 2.26 – 2.46 (m, 2 H) 1.39 (s, 9 H); MS (APCI+) m/z 418.2 (M+H)+.

According to the analysis of related databases, 65896-11-9, the application of this compound in the production field has become more and more popular.

Reference:
Patent; ABBOTT LABORATORIES; ABBOTT GMBH &; CO. KG; WANG, Ying; BREWER, Jason, T.; AKRITOPOULOU-ZANZE, Irini; DJURIC, Stevan, W.; POHLKI, Frauke; BRAJE, Wilfried; RELO, Ana-Lucia; WO2010/124042; (2010); A2;,
Bromide – Wikipedia,
bromide – Wiktionary

Adding a certain compound to certain chemical reactions, such as: 65896-11-9, name is 2-Bromo-6-fluoroaniline, 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 65896-11-9, Quality Control of 2-Bromo-6-fluoroaniline

[0676] 2-Propylzinc bromide (0.50 M in THF, 16 mL, 7.9 mmol, Sigma-Aldrich Corporation, St. Louis, MO, USA) was added to a stirred mixture of 2-bromo-6-fluoroaniline (1.00 g, 5.26 mmol, Acros, Geel, Belgium), palladium (II) acetate (0.059 g, 0.263 mmol), and 2-dicyclohexylphosphino-2′,6′-dimethylamino-1,1′-biphenyl (0.230 g, 0.526 mmol, Strem Chemicals, Newburyport, MA) in THF (10 mL), and the resulting mixture was stirred under Ar(g) in a sealed vial at rt for 3 h. The reaction mixture was then diluted with satd. aq. ammonium chloride and extracted with EtOAc. The organic extract was then washed with brine, dried over MgSO4, filtered, and concentrated in vacuo. Chromatographic purification of the residue (silica gel, eluent: 0-25% EtOAc in heptane) gave 2-fluoro-6-isopropylaniline as a yellow oil (Intermediate I-26, 618 mg, 4.03 mmol, 77 % yield).1H NMR (400 MHz, CDCl3) d ppm 6.92 (1H, d, J=7.88 Hz) 6.86 (1H, ddd, J=10.73, 8.14, 1.24 Hz) 6.69 (1H, td, J=7.88, 5.60 Hz) 3.70 (2 H, br s) 2.92 (1H, spt, J=6.84 Hz) 1.26 (6 H, d, J=6.84 Hz). m/z (ESI, +ve ion): 154.1 (M+H)+.

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; AMGEN INC.; ALLEN, John Gordon; ALLEN, Jennifer Rebecca; MINATTI, Ana Elena; XUE, Qiufen; WURZ, Ryan Paul; TEGLEY, Christopher M.; PICKRELL, Alexander J.; NGUYEN, Thomas T.; MA, Vu Van; LOPEZ, Patricia; LIU, Longbin; KOPECKY, David John; FROHN, Michael J.; CHEN, Ning; CHEN, Jian Jeffrey; SIEGMUND, Aaron C.; AMEGADZIE, Albert; TAMAYO, Nuria A.; BOOKER, Shon; GOODMAN, Clifford; WALTON, Mary; NISHIMURA, Nobuko; SHIN, Youngsook; LOW, Jonathan D.; CEE, Victor J.; REED, Anthony B.; WANG, Hui-Ling; LANMAN, Brian Alan; (738 pag.)WO2019/213516; (2019); A1;,
Bromide – Wikipedia,
bromide – Wiktionary

Application of 65896-11-9, 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 65896-11-9 as follows.

Example 1A Methyl (2E)-3-[2-amino-3-fluorophenyl]propenoate Starting with 42.00 g (221.04 mmol) of 2-bromo-6-fluoroaniline, the general procedure [A] gives 29.66 g (68% of theory) of product. HPLC (method 1): Rt=4.14 min MS (ESI-pos): m/z=196 (M+H)+

According to the analysis of related databases, 65896-11-9, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Bayer HealthCare AG; US2007/281953; (2007); A1;,
Bromide – Wikipedia,
bromide – Wiktionary

Some common heterocyclic compound, 65896-11-9, name is 2-Bromo-6-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. Application In Synthesis of 2-Bromo-6-fluoroaniline

At 15 deg.C, 2-bromo-6-fluoroaniline (1.00 g, 5.26 mmol) and dimethylphosphine oxide (451.84 mg, 5.79 mmol) in water (20ml) mixture was added potassium carbonate ( 2.91 g, 21.05 mmol) and Pd / C (150 mg). The reaction mixture was stirred at 160 deg.C microwave heating for 3 hours. TLC (petroleum ether: ethyl acetate = 10: 1) showed the reaction was complete. The reaction mixture (20mL × 4) and extracted with dichloromethane. The combined organic layer was filtered, the filtrate was concentrated and purified by column chromatography (dichloromethane: methanol = 1: 0-10: 1) afforded the title compound (100mg, yield 10.16%) as a yellow solid.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 65896-11-9, its application will become more common.

Reference:
Patent; Nanjing Mingde New Drug Research and Development Co. Ltd.; Qilu Pharmaceutical Co., Ltd.; Ding, Zhaozhong; Zhang, Minghui; Chen, Shuhui; Liu, Xile; Zhu, Yidong; Fan, Chuanwen; Zhao, Baoping; Zhang, Long; Chen, Dong; Yang, Yingying; Zheng, Qingmei; Zheng, Shansong; Wan, Haiwen; Hu, Jinqing; (93 pag.)CN105330698; (2016); A;,
Bromide – Wikipedia,
bromide – Wiktionary

Synthetic Route of 65896-11-9, 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. 65896-11-9, name is 2-Bromo-6-fluoroaniline belongs to bromides-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below.

General procedure: A Schlenk tube was charged with Oxone (0.398 g, 0.648mmol) and trifloroacetic acid (0.099 mL, 1.296 mmol) in anhydrous dioxane (2 mL) under argon. To this mixture was added 2-fluoroaniline (0.06 g, 0.54 mmol), and the reaction mixture was heated to 90 C under argon until starting material was consumed. As the reaction progressed, the color turned from lightred to dark red. The mixture was then cooled to room temperature and washed with a saturated aqueous sodium bicarbonate.The mixture was extracted with EtOAc (2 ¡Á 20 mL) and the combined organic layers were dried over Na2SO4. After filtering andremoval of the solvent under reduced pressure in vacuo, theresidue was purified by silica gel (100-200 mesh) column chromatography(hexane-EtOAc, 9:1), to afford a pale-brown solid(65%) of 2-hydroxy-N-trifluoroacetanilides from 2-fluoroaniline(2a).

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, 2-Bromo-6-fluoroaniline, other downstream synthetic routes, hurry up and to see.

Reference:
Article; Venkateswarlu, Vunnam; Balgotra, Shilpi; Aravinda Kumar; Vishwakarma, Ram A.; Sawant, Sanghapal D.; Synlett; vol. 26; 9; (2015); p. 1258 – 1262;,
Bromide – Wikipedia,
bromide – Wiktionary

Synthetic Route of 65896-11-9, 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. 65896-11-9, name is 2-Bromo-6-fluoroaniline, This compound has unique chemical properties. The synthetic route is as follows.

A mixture of 5,8-dimethoxy-1,2,3,4-tetrahydro-1,4-methanonaphthalene-6-carbaldehyde 1 (0.23g, 0.97mmol), 2-bromo-6-fluoroaniline 9c (1 equiv, 0.18g, 0.97mmol), NaCNBH3 (2.5 equiv, 0.15g, 2.4mmol) and acetic acid (2 equiv, 0.12g, 1.9mmol) in iso-propanol (20mL) was stirred at room temperature for seven days. After this time, a saturated aqueous solution of Na2CO3 (15mL) was added and an extraction with EtOAc was performed (3¡Á15mL). After drying of the combined organic phases (MgSO4), filtration and evaporation, crude aniline 10c was obtained, which was purified by reverse phase automated flash chromatography (0.080g, 0.19mmol). 2-Bromo-N-[(5,8-dimethoxy-1,2,3,4-tetrahydro-1,4-methanonaphthalen-6-yl)methyl]-6-fluoroaniline 10c. Pale yellow oil. Gradient used for purification: during 3 CV: 40% CH3CN, during 30 CV: 40 -> 100% CH3CN, during 3 CV: 100% CH3CN. Yield 20%. 1H NMR (400MHz, CDCl3): delta 1.17-1.28 (2H, m), 1.48 (1H, ddd, J=8.7Hz, 1.4Hz, 1.4Hz), 1.69-1.72 (1H, m), 1.86-1.98 (2H, m), 3.55-3.57 (1H, m), 3.62-3.64 (1H, m), 3.76 (3H, s), 3.86 (3H, s), 4.38 (1H, br s), 4.47 (2H, d, J=4.4Hz), 6.61 (1H, ddd, J=8.2Hz, 8.1Hz, JH,F=4.9Hz), 6.95 (1H, ddd, JH,F=12.4Hz, J=8.2Hz, 1.4Hz), 7.22 (1H, ddd, J=8.1Hz, 1.4Hz, 1.3Hz). 13C NMR (100.6MHz, ref=CDCl3): delta 26.6, 27.1, 39.7, 41.5, 46.7 (d, J=9.6Hz), 49.1, 56.0, 61.5, 110.2, 113.9 (d, J=5.5Hz), 116.0 (d, J=21.3Hz), 119.6 (d, J=8.5Hz), 128.2 (d, J=3.1Hz), 129.5, 135.4 (d, J=12.0Hz), 136.5, 140.3, 146.3, 148.9, 153.4 (d, J=245.0Hz). 19F NMR (376.5MHz, CDCl3, ref=CFCl3): delta-124.10 (1F, dd, JH,F=12.4Hz, 4.9Hz). MS (ES+): m/z (%): 217 (100).

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

Reference:
Article; Cappoen, Davie; Torfs, Eveline; Meiresonne, Tamara; Claes, Pieter; Semina, Elena; Holvoet, Francis; de Macedo, Maira Bidart; Cools, Freya; Piller, Tatiana; Matheeussen, An; Van Calster, Kevin; Caljon, Guy; Delputte, Peter; Maes, Louis; Neyrolles, Olivier; De Kimpe, Norbert; Mangelinckx, Sven; Cos, Paul; European Journal of Medicinal Chemistry; vol. 181; (2019);,
Bromide – Wikipedia,
bromide – Wiktionary