Category: 57946-63-1

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. Computed Properties of C7H5BrF3N

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

Synthetic Route of 57946-63-1, 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. 57946-63-1, name is 2-Bromo-4-(trifluoromethyl)aniline belongs to bromides-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below.

Intermediate 41 8-bromo-3-methyl-6-(trifluoromethyl)quinoline. 2-bromo-4-(trifluoromethyl)aniline (5 g, 20.83 mmol) was added to 6N HCl (20.83 mL). The mixture was heated to reflux and added methacrolein (3.96 mL, 47.9 mmol) dropwise over 20 minutes via addition funnel. Reflux was continued at 100° C. overnight then the mixture was cooled and adjusted to pH ~5-6 using NH4OH (aq). The mixture was extracted with ether (2*100 ml). The combined organic layers were washed with brine, dried over MgSO4, filtered then concentrated and purified by column chromatography (SiO2) eluding with 10-30percent EtOAc in hexanes to give the product (930 mg, 15percent). 1H NMR (400 MHz, MeOD) delta ppm 8.81 (1H, dd, J=4.28, 1.76 Hz), 8.19 (1H, dd, J=8.44, 1.64 Hz), 7.94 (1H, d, J=2.27 Hz), 7.47 (1H, dd, J=8.31, 4.28 Hz), 7.36-7.43 (2H, m), 7.29 (1H, d, J=2.01 Hz), 7.06 (2H, t, J=8.94 Hz), 5.44-5.52 (1H, m, J=6.80 Hz), 3.33 (2H, s), 2.53-2.71 (2H, m), 2.19 (3H, s), 2.02-2.39 (5H, m), 1.92-2.03 (1H, m), 1.35 (3H, d, J=6.30 Hz). Mass 291.79 [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, 2-Bromo-4-(trifluoromethyl)aniline, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; Bristol-Myers Squibb Company; US2009/18163; (2009); A1;,
Bromide – Wikipedia,
bromide – Wiktionary

Adding a certain compound to certain chemical reactions, such as: 57946-63-1, name is 2-Bromo-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 57946-63-1, Recommanded Product: 2-Bromo-4-(trifluoromethyl)aniline

This compound was prepared by application of the procedure for oxidation of4-(trifluoromethyl)aniline.[7] A 300 mL three-necked round-bottom flask equipped with a refluxcondenser and a dropping funnel was charged with sodium perborate tetrahydrate (40.69 g, 0.264mol) and glacial acetic acid (50 mL). The dropping funnel was charged with2-bromo-4-(trifluoromethyl)aniline (6.31 g, 26.8 mmol) and glacial acetic acid (50 mL). Thesuspension in the flask was heated to 55°C and the content of the funnel was added dropwise to it.After 3 h, an additional sodium perborate tetrahydrate (20.00 g, 0.130 mol) was added to the reactionmixture and stirred at 55°C for 4 h. The resulting yellow suspension was cooled to room temperatureand filtered through a Celite pad. To the filtrate was added diethyl ether (200 mL) and water (100mL). The organic phase was separated from the mixture and aqueous phase was extracted withdiethyl ether (150 mL x 2). Combined organic phase was neutralized by aqueous sodium hydroxidesolution (3 M) and separated. The separated organic phase was dried over sodium sulfate andconcentrated to afford brown liquid. This crude product was purified by flash columnchromatography (12percent EtOAc/hexane) to give the title compound as a yellow liquid (4.22 g, 60 percent).

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:
Article; Takahashi, Hirotsugu; Watanabe, Takahito; Tobita, Hiromi; Chemistry Letters; vol. 47; 3; (2018); p. 296 – 299;,
Bromide – Wikipedia,
bromide – Wiktionary

Related Products of 57946-63-1, 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. 57946-63-1, name is 2-Bromo-4-(trifluoromethyl)aniline belongs to bromides-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below.

General procedure: To a stirred solution of 2-haloaniline derivatives in DCM, Et3N (1.3 equiv.) was added and the resulting mixture was cooled to 0 °C. Stirred for 5 min and acid chloride (1.1 equiv.) was added drop wise. Stirred overnight from 0 °C to RT. The reaction mixture was extracted with DCM and washed with NaHCO3 and brine. The organic phase was dried over anhydrous sodium sulphate and the solvent was evaporated using vacuum rotary evaporator. The resulting residue was purified on silica gel column chromatography using n-hexane and ethyl acetate as eluent.

The synthetic route of 2-Bromo-4-(trifluoromethyl)aniline has been constantly updated, and we look forward to future research findings.

Reference:
Article; Venu Saranya, Thachora; Rajan Sruthi, Pambingal; Anas, Saithalavi; Synthetic Communications; vol. 49; 2; (2019); p. 297 – 307;,
Bromide – Wikipedia,
bromide – Wiktionary

Adding a certain compound to certain chemical reactions, such as: 57946-63-1, name is 2-Bromo-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 57946-63-1, Recommanded Product: 57946-63-1

A solution of 2-bromo-4-(trifluoromethyl)aniline (5.00 g, 20.8 mmol), tri(o- tolyl)phosphine (1.27 g, 4.18 mmol), palladium (II) acetate (460 mg, 2.78 mmol), methyl prop-2- enoate (9.00 g, 104 mmol), and triethylamine (6.57 mL, 47.1 mmol) in acetonitrile (100 mL) was heated to 90 C overnight. The reaction mixture was filtered, and the filtrate was concentrated under vacuum. The residue was purified via column chromatography on silica gel (eluting with 25% ethyl acetate-petroleum ether) to give (E)-methyl 3-(2-amino-5- (trifluoromethyl)phenyl)acrylate (3.4 g, 67%) as a yellow solid. MS: (ES, m/z ): 246[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, 2-Bromo-4-(trifluoromethyl)aniline, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; FORMA THERAPEUTICS, INC.; ZHENG, Xiaozhang; MARTIN, Matthew W.; NG, Pui Yee; THOMASON, Jennifer R.; HAN, Bingsong; RUDNITSKAYA, Aleksandra; LANCIA, JR., David R.; (180 pag.)WO2019/204550; (2019); 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. 57946-63-1, name is 2-Bromo-4-(trifluoromethyl)aniline, A new synthetic method of this compound is introduced below., COA of Formula: C7H5BrF3N

4-Amino-3-bromobenzotrifluoride (15.0 g, 62.5 mmol) was dissolved in N,N-dimethylformamide (400 mL). Thereafter, sodium hydride (5.0 g, 126 mmol) was added to the above obtained solution under cooling on ice, and the thus obtained mixture was then stirred at room temperature for 2 hours. Thereafter, an N,N-dimethylformamide (30 mL) solution of the tert-butyl 3-(chloromethyl)-2,5-dihydro-1H-pyrrole-1-carboxylate (9.20 g, 42.0 mmol) synthesized by a method described in the known methods ( etc.) or a method similar thereto was further added to the reaction solution under cooling on ice, and the thus obtained mixture was then stirred at room temperature for 3 hours. Subsequently, water was added to the reaction solution, and the mixed solution was then extracted with ethyl acetate. The organic layer was washed with brine, and was then dried over anhydrous sodium sulfate, followed by concentration in vacuo. The obtained residue was purified by silica gel column chromatography (hexane : ethyl acetate = 3 : 1) to obtain tert-butyl 3-(((2-bromo-4-(trifluoromethyl)phenyl)amino)methyl)-2,5-dihydro-1H-pyrrole-1-carboxylate (6.46 g, 37percent) in the form of a colorless amorphous product. 1H-NMR (400 MHz, CDCl3) delta: 1.46 (9H, s), 3.93 (2H, m), 4.13 (4H, m), 4.88 (1H, m), 5.64 (1H, m), 6.61 (1H, m), 7.39 (1H, m), 7.67 (1H, s)

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; Kowa Company, Ltd.; OGAMINO, Takahisa; YAMAZAKI, Yukiyoshi; TANIKAWA, Shin; OKUDA, Ayumu; FUKUDA, Tomoaki; TOKUDA, Okihisa; MIYAKE, Yoshiharu; ITOH, Shinsuke; ISHIWATA, Hiroyuki; (205 pag.)EP2781521; (2014); A1;,
Bromide – Wikipedia,
bromide – Wiktionary

Some common heterocyclic compound, 57946-63-1, name is 2-Bromo-4-(trifluoromethyl)aniline, molecular formula is C7H5BrF3N, 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. HPLC of Formula: C7H5BrF3N

A 100 ml 3-neck flask with magnetic stirrer was charged with 2-bromo-4- (trifluoromethyl)aniline (500 mg, 2.08 mmol), methyl acrylate (538 mg, 6.25 mmol), Pd(OAc)2 (23.3 mg, 0.104 mmol), P(o-tolyl)3 (64 mg, 0.21 mmol), triethylamine (422 mg, 4.7 mmol) and acetonitrile (20 ml). The flask was purged with N2 and heated to 90 C overnight. Saturated aqueous NH4CI (40ml) was added, and the mixture was extracted with ethyl acetate (10 ml*3). The organic layer was dried over Na2S04, filtered, and concentrated to dryness. The crude product was purified by silica gel chromatography to give (£)-methyl 3-(2-amino-5-(trifluoromethyl)phenyl)acrylate (185.9 mg, 36.5%) as a yellow solid. 1 H NMR (400 MHz, CDCI3) delta 7.69 (d, J=16 Hz, 1 H), 7.53 (s, 1 H), 7.32 (d, J=8.8 Hz, 1 H), 6.67 (d, J=8.8 Hz, 1 H), 6.34 (d, J=16 Hz, 1 H), 4.20 (s, 2H), 3.74 (s, 3H).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 57946-63-1, its application will become more common.

Reference:
Patent; PFIZER INC.; DIDIUK, Mary; FILIPSKI, Kevin J.; GUZMAN-PEREZ, Angel; LEE, Esther C.; PFEFFERKORN, Jeffrey A.; STEVENS, Benjamin; TU, Meihua; WO2013/14569; (2013); A1;,
Bromide – Wikipedia,
bromide – Wiktionary

Related Products of 57946-63-1, These common heterocyclic compound, 57946-63-1, name is 2-Bromo-4-(trifluoromethyl)aniline, 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.

Diethyl ethoxymethylenemalonate (2.3 g, 10.6 mmol, 2.5 eq.) was added to a solution of 2-bromo-4-(trifluoromethyl)aniline (25) (1.0 g, 4.2 mmol, 1.0 eq.) in toluene (6 mL). The resulting mixture was refluxed for 11 h. After cooling to room temperature, the solvent was evaporated under reduced pressure. The residue obtained was purified by column chromatography (SiO2, cyclohexane/ethyl acetate, 100/0 to 80/20, v/v) to afford the desired product 26 (1.5 g, 3.7 mmol, 88percent) as a white solid. Rf (SiO2, cyclohexane/ethyl acetate, 9/1, v/v): 0.34; Mp: 90-92 °C; IR (cm-1): 1682 (nuC=O), 1646 (nuC=C), 1596 (deltaN-H), 1321 (nuCF3), 1245 (nuas C-O-C), 1077 (nus C-O-C); 1H NMR (CDCl3, 400 MHz) delta 11.38 (d, 1H, 3JNH-Ha= 12.7 Hz, NH), 8.48 (d, 1H, 3JHa-NH = 12.7 Hz, Ha), 7.86 (d, 1H, 4JH3-H5= 1.4 Hz, H3), 7.61 (m, 1H, H5), 7.36 (d, 1H, 3JH6-H5= 8.5 Hz, H6), 4.36 (q, 2H, 3JHd-He or Hd?-He?= 7.1 Hz, Hd or Hd?), 4.28 (q, 2H, 3JHd-He or Hd?-He?= 7.1 Hz, Hd or Hd?), 1.39 (t, 3H, 3JHe-Hd or He?-Hd?= 7.1 Hz, He or He?), 1.34 (t, 3H, 3JHe-Hd or He?-Hd?= 7.1 Hz, He or He?); 13C NMR (DMSO-d6, 125 MHz) delta 167.9 (Cc or Cc?), 164.8 (Cc or Cc?), 150.0 (Ca), 140.9 (C1), 130.5 (d, 3JC3-F = 4 Hz, C3), 126.6 (d, 3JC5-F = 4 Hz, C5), 125.6 (q, 2JC4-F = 33 Hz, C4), 123.7 (d, 1JCF3-F = 270 Hz, CF3), 117.2 (C2), 112.9 (C6), 97.5 (Cb), 60.7 (Cd or Cd?), 60.4 (Cd or Cd?), 14.6 (Ce or Ce?), 14.5 (Ce or Ce?); HRMS calculated for C15H1579BrF3NO4 [M+H]+ m/z 410.0215, found C15H1579BrF3NO4 [M+H]+ m/z 410.0189 (100percent); C15H1581BrF3NO4 [M+H]+ m/z 412.0157 (98percent).

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

Reference:
Article; Liu, Jianrong; Maisonial-Besset, Aurelie; Wenzel, Barbara; Canitrot, Damien; Baufond, Ariane; Chezal, Jean-Michel; Brust, Peter; Moreau, Emmanuel; European Journal of Medicinal Chemistry; vol. 136; (2017); p. 548 – 560;,
Bromide – Wikipedia,
bromide – Wiktionary

Application of 57946-63-1, 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 57946-63-1 as follows.

Commercially available 2-bromo-4-(trifluoromethyl)benzeneamine (2.06 g, 8.6 mmol) was suspended in concentrated HCl (4.0 mL). Clumps of material were broken up with a spatula, then ice (-2.6 g) was added to the mixture and it was cooled over an ice bath. A solution of NaNO2 (0.64 g, 9.3 mmol) in H2O (2.6 mL) was added dropwise while maintaining the temperature of the reaction mixture at 0-50C. The mixture was stirred for 20 minutes over the ice bath, then poured slowly into a solution of KI (12.5 g, 75.3 mmol) in H2O (16 mL). The BCI mixture was stirred for several minutes, then left to settle over night. EPO The reaction mixture was extracted thrice with hexanes. The combined organics were washed twice with IM NaOH, once with aqueous sodium bisulfite solution, then with brine. The solution was dried over MgSO4, vacuum filtered through Celite.(R). and cone in vacuo to give 2.33 g of 2-bromo-4-(trifluoromethyl)-iodobenzene. By TLC (100percent hexanes) and 1H NMR analysis, it was determined that the product was of sufficient purity to be used in the subsequent step. The resultant diethyl [2-bromo-4-(trifluoromethyl)- phenyljdifluoromethylphosphonate was synthesized from 2-bromo-4-(trifluoromethyl)- iodobenzene according to Example 25 except that chlorotrimethylsilane (several drops) was used in place of acetic acid. Compound 86 was synthesized according to procedures similar to those of Example 40 from this corresponding diethyl phosphonate. MS (ES-):m/z 352.9, 354.9 (M – H). 1H NMR: (DMSO-d6, 400 MHz) delta 8.07 (s, IH), 7.89 (d, J = 8.0, IH), 7.78 (d, J = 8.0, IH).

According to the analysis of related databases, 57946-63-1, the application of this compound in the production field has become more and more popular.

Reference:
Patent; CEPTYR, INC.; WO2006/55525; (2006); A2;,
Bromide – Wikipedia,
bromide – Wiktionary

Electric Literature of 57946-63-1, 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 57946-63-1 as follows.

EXAMPLE 6 4-(2-Bromo-4-trifluoromethyl-phenylcarbamoyl)-piperidine-1-carboxylic acid tert-butyl ester Piperidine-1,4-dicarboxylic acid mono-tert-butyl ester (4.90 g, 21.00 mmol) was dissolved in dry methylene chloride (30 mL) and dry pyridine (4.30 mL). To the reaction mixture was then added thionyl chloride (3.00 g, 25.20 mmol) under nitrogen atmosphere and the reaction mixture was stirred at room temperature for 30 minutes. To the reaction mixture was then added successively, under nitrogen atmosphere, 2-bromo-4-trifluoromethyl-phenylamine (5.60 g, 23.50 mmol), dry triethylamine (7.43 g, 73.5 mmol), dry methylene chloride (38 mL), 4-(dimethylamino)pyridine (0.26 g, 2.18 mmol) and the reaction mixture was stirred at room temperature for 24 hours. The reaction mixture was then partitioned with aqueous 2N HCl and tert-butyl methyl ether. The organic layer was washed with aqueous 2N HCl, aqueous NaHCO3, brine, dried with Na2SO4, filtered and the solvent evaporated in vacuo to yield a crude oil. The crude oil was purified via flash chromatography (30percent ethyl acetate/hexanes) to yield the title compound as an oil. 1H NMR (300 MHz, CDCl3) delta 8.5 (1H, d, J=9 Hz), 7.6 (1H, bs) 7.5 (1H, d, J=7.0 Hz), 7.3 (1H, d, J=8 Hz), 4.18 (2H, m), 2.8 (2H, m), 1.9 (2H, d), 1.8 (2H, m), 1.47 (9H, s) MS (ES+) m/z 475.0 (MNa)+

According to the analysis of related databases, 57946-63-1, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Battista, Kathleen A.; Bignan, Gilles C.; Connolly, Peter J.; Liu, Jessica J.; Middleton, Steven A.; Orsini, Michael J.; US2007/112016; (2007); A1;,
Bromide – Wikipedia,
bromide – Wiktionary