Category: 38762-41-3

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. 38762-41-3, name is 4-Bromo-2-chloroaniline, A new synthetic method of this compound is introduced below., HPLC of Formula: C6H5BrClN

2-Fluoro-4-bromoaniline (3.83 g, 18.55 mmol) was added to a reaction flask, then anhydrous tetrahydrofuran (20 ml) was added, and the mixture was cooled to -78 C with a dry ice ethanol bath, and LiHMDS (55.65 ml, 55.65 mmol), after reacting at -78 C for 30 minutes, methyl 2-chloro-1,5-dimethyl-6-oxo-1,6-dihydropyridine-3-carboxylate (4.00) was added. g, 18.55 mmol), after completion, the reaction was stirred at -78 C for 1 hour. After the completion of the reaction, the mixture was stirred at room temperature, and the reaction was quenched with saturated aqueous ammonium chloride.Column chromatography to obtain compounds(6.0 g, yield: 83.9%).

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; BINJIANG PHARMA INC; Tianjin Binjiang Pharmaceutical Research And Development Co., Ltd.; TIAN HONGQI; Tian Hongqi; (39 pag.)CN109988105; (2019); A;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

38762-41-3, name is 4-Bromo-2-chloroaniline, belongs to chlorides-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. COA of Formula: C6H5BrClN

[00219] Step C: 4-(4-Bromo-2-chlorophenylamino)-6-chloronicotinic acid:[00220] To a solution of 2-chloro-4-bromoaniline (6.776 g, 33.1 mmol) in 50 ml anhydrous THF was added LHMDS (50 ml, 50 mmol, 1M/THF) over a period of 15 min at -78 C. It was stirred for an additional 30 min., then a solution of 4,6-dichloronicotinic acid (3 g, 15.7 mmol) in 50 ml THF was added dropwise. After complete addition the mixture was gradually allowed to warm to room temperature and the reaction mixture was stirred for an additional 12 hours. The mixture was quenched with H2O and 1N HCl was added (pH 0-1) followed by brine. It was extracted using THF and dried with Na2SO4. The solvent was removed and the solid crude product was suspended in 200 ml EtOAc. The suspension was heated with stirring at the reflux temperature for 5 min. It was cooled to room temperature and the precipitate was filtered and washed with EtOAc and dried at 50 C for 5 h in oil pump vacuo to obtain the title compound as an off-white solid (4.05 g, 72%). Rf (CHCl3/MeOH 10:1 ) = 0.3. 1H-NMR (500 MHz, DMSO-D6): delta = 10.12 (s, 1H), 8.65 (s, 1H), 7.88 (s, 1H), 7.62-7.57 (dd, 1H), 7.55-7.48 (dd, 1H), 6.67 (s, 1H).

The synthetic route of 38762-41-3 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; ARDEA BIOSCIENCES, INC.; WO2008/89459; (2008); A1;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

Reference of 38762-41-3, The chemical industry reduces the impact on the environment during synthesis 38762-41-3, name is 4-Bromo-2-chloroaniline, I believe this compound will play a more active role in future production and life.

Description 13; (4-Bromo-2-chlorophenyl)-(tetrahydropyran-4-yl)-amine (D13); A mixture of 4-bromo-2-chloro-phenylamine (0.5 g, 2.422 mmol), tetrahydropyran-4- one (1.308 ml, 10.898 mmol), and sodium triacetoxyborohydride (2.31 g, 10.898 mmol) in DCE (20 ml) was stirred at room temperature for 16 h. The reaction mixture was washed with NaHCO3 (aqueous sat. solution), dried (Na2SO4) and the solvent was evaporated in vacuo. The residue was purified by column chromatography (silica gel; heptane/DCM up to 40% as eluent). The desired fractions were collected and evaporated in vacuo to yield compound D13 (0.383 g, 52%) as white solid. LCMS: MW (theor): 289; [MH+]: 290; RT (min): 4.39 (Method 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-chloroaniline, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; ORTHO-MCNEIL-JANSSEN PHARMACEUTICALS, INC.; ADDEX PHARMA S.A.; CID-NUNEZ, Jose, Maria; TRABANCO-SUAREZ, Andres, Avelino; MACDONALD, Gregor, James; WO2010/60589; (2010); A1;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

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. 38762-41-3, name is 4-Bromo-2-chloroaniline, A new synthetic method of this compound is introduced below., Recommanded Product: 4-Bromo-2-chloroaniline

Preparation 94 2-Chloro-4-(oxazol-5-yl)aniline Palladium acetate (5.4 mg, 0.024 mmol) was added to a solution of 4-bromo-2-chloroaniline (0.1 g, 0.484 mmol), oxazole (0.064 mL, 0.969 mmol), di(1-adamantyl)-n-butylphosphine (0.017 g, 0.048 mmol), pivalic acid (0.020 g, 0.194 mmol) and potassium carbonate (0.201 g, 1.453 mmol) in DMA (2.4 mL). The reaction mixture was heated at 110 C. overnight before being diluted with EtOAc and quenched with water. The layers were separated and the aqueous layer was extracted with EtOAc. The combined organic layers were dried (Na2SO4), filtered and concentrated under reduced pressure. The crude mixture was purified via Biotage silica gel column chromatography eluting with (Cyclohexane/EtOAc 80/20 to 60/40) to give the title product as a white solid (35 mg, 37%). 1H NMR (500 MHz, CDCl3): delta 4.25 (br s, 2H), 6.82 (d, J=8.3 Hz, 1H), 7.20 (s, 1H), 7.38 (dd, J=8.3, 2.0 Hz, 1H), 7.58 (d, J=2.0 Hz, 1H), 7.87 (s, 1H). LC (Method B)-MS (ESI, m/z) tR 2.47 min, 195 [(M+H+), 100%].

The synthetic route of 38762-41-3 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; CANCER RESEARCH TECHNOLOGY LIMITED; Bavetsias, Vassilios; Atrash, Butrus; Naud, Sebastien Gaston Andre; Sheldrake, Peter William; Blagg, Julian; US2013/345181; (2013); A1;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

Electric Literature of 38762-41-3, 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 38762-41-3 as follows.

To a solution of 4-bromo-2-chloro-phenylamine (32 g, 0.15 mol) and pyridine (13.45 g, 0.17 mol) in DCM (200 mL) was added 3-chloropropionyl chloride (21.65 g, 0.17 mol) dropwise at 15 C. After stirring at room temperature for 1 hour, the mixture was washed with water and then aqueous 2N HC1. The organic layer was dried over anhy. Na2S04, filtered, and concentrated in vacuo to afford title compound (10.9 g, 90%) as a white solid.

According to the analysis of related databases, 38762-41-3, the application of this compound in the production field has become more and more popular.

Reference:
Patent; F. HOFFMANN-LA ROCHE AG; HOFFMANN-LA ROCHE INC.; AEBI, Johannes; AMREIN, Kurt; HORNSPERGER, Benoit; KUHN, Bernd; MAERKI, Hans P.; MARTIN, Rainer E.; MAYWEG, Alexander V.; TAN, Xuefei; (77 pag.)WO2016/66597; (2016); A1;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

Application of 38762-41-3, 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. 38762-41-3 name is 4-Bromo-2-chloroaniline, 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.

Synthesis of methyl 4?-amino-3 ?-chlorobiphenyl-4-carboxylate (65): A mixture of 4-bromo-2-chloroaniline (10 g, 48.5 mmol), 4-(methoxycarbonyl)phenylboronic acid (9.6 g,53.4 mmol), Pd(dppf)C12 (3.6 g, 4.85 mmol) and K2C03 (13.4 g, 97 mmol) in dioxane (100 mL) and water (10 mL) was degassed and heated at 100C for 2 h. After cooling down to room temperature, the reaction mixture was poured into water, extracted with EtOAc (100 mL X 3). The combined organic solvents were dried over anhydrous Na2504, concentrated under reduced pressure and purified by silica gel chromatography (10-50% EtOAc/petroleum ether) to give 11 g of methyl 4?-amino-3?-chlorobiphenyl-4-carboxylate 65 as black solid (86% yield). LCMS: m/z 262.1 [M+H], , tR= 1.98 min

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

Reference:
Patent; KARYOPHARM THERAPEUTICS INC.; BALOGLU, Erkan; SHACHAM, Sharon; SENAPEDIS, William; (153 pag.)WO2017/31213; (2017); A1;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

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 38762-41-3 as follows. Recommanded Product: 38762-41-3

Preparation 94: 2-Chloro-4-(oxazol-5-yl)aniline; [00264] Palladium acetate (5.4mg, 0.024mmol) was added to a solution of 4-bromo-2- chloroaniline (0.1 g, 0.484mmol), oxazole (0.064mL, 0.969mmol), di(1 -adamantyl)-/> butylphosphine (0.017g, 0.048mmol), pivalic acid (0.020g, 0.194mmol) and potassium carbonate (0.201 g, 1 .453mmol) in DMA (2.4ml_). The reaction mixture was heated at 1 10 C overnight before being diluted with EtOAc and quenched with water. The layers were separated and the aqueous layer was extracted with EtOAc. The combined organic layers were dried (Na2S04), filtered and concentrated under reduced pressure. The crude mixture was purified via Biotage silica gel column chromatography eluting with (Cyclohexane/EtOAc 80/20 to 60/40) to give the title product as a white solid (35mg, 37%). 1 H NMR (500 MHz, CDCI3): delta 4.25 (br s, 2H), 6.82 (d, J = 8.3Hz, 1 H), 7.20 (s, 1 H), 7.38 (dd, J = 8.3, 2.0Hz, 1 H), 7.58 (d, J = 2.0Hz, 1 H), 7.87 (s, 1 H).LC (Method B)-MS (ESI, m/z) fR 2.47 min, 195 [(M+H+), 100%].

According to the analysis of related databases, 38762-41-3, the application of this compound in the production field has become more and more popular.

Reference:
Patent; CANCER RESEARCH TECHNOLOGY LIMITED; BAVETSIAS, Vassilios; ATRASH, Butrus; NAUD, Sebastien Gaston Andre; SHELDRAKE, Peter William; BLAGG, Julian; WO2012/123745; (2012); A1;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

Related Products of 38762-41-3,Some common heterocyclic compound, 38762-41-3, name is 4-Bromo-2-chloroaniline, molecular formula is C6H5BrClN, 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. Tert-butyl N-(4-bromo-2-chlorophenyl)carbamate A solution of 4-bromo-2-chloroaniline (5.00 g, 0.0242 mol) in tetrahydrofuran (50 mL) was reacted with a 1.0 M solution of sodium bis(trimethylsilyl)amide in tetrahydrofuran (53.2 mL, 0.0532 mol). The mixture was stirred 15 minutes at ambient temperature. Di-tert-butyl dicarbonate (6.34 g, 0.0290 mol) was added and the solution was stirred for 2 hours. The solvent was removed in vacuo, and the crude material was purified by flash column chromatography on silica using heptane /ethyl acetate (4:1). The solvent was removed in vacuo to give tert-butyl N-(4-bromo-2-chlorophenyl)carbamate as a white solid (4.214 g, 0.0137 mol). 1H NMR (DMSO-d6, 400 MHz) delta 8.75 (s, 1H), 7.71 (d, 1H), 7.54 (d, 1H), 7.50 (dd, 1H), 1.46 (s, 9H); TLC (heptane/ethylacetate 4:1) Rf 0.54.

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-2-chloroaniline, its application will become more common.

Reference:
Patent; Abbott Laboratories; US2002/156081; (2002); A1;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

Related Products of 38762-41-3, A common heterocyclic compound, 38762-41-3, name is 4-Bromo-2-chloroaniline, molecular formula is C6H5BrClN, 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: Experimental Procedure: A dried 25 mL Schlenk tube equipped with a magnetic stir bar was charged with Togni?s Reagent 2 (0.25 mmol, 1.0 equiv), free anilines 1 (0.75 mmol, 3.0 equiv), K2CO3 (0.375 mmol, 1.5 equiv) and CH3CN (1.5 mL). The reaction mixture was then stirred at 75 C for 6 h under an argon atmosphere. The reaction progress was monitored by TLC. After cooling to room temperature, the mixture was washed with water and extracted with CH2Cl2 three times, then washed with saturated NaCl solution. The combined organic layer was dried with anhydrous Na2SO4 and filtered. The filtrate was concentrated in vacuo. The crude product was purified by flash column chromatography on silica gel (Elutent: petroleum ether-EtOAc) to give the pure product. The products were characterized by 1H NMR, 13C NMR, 19F NMR, GC -MS.

The synthetic route of 38762-41-3 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Chen, Xiaoyu; Ding, Licheng; Li, Linlin; Li, Jingya; Zou, Dapeng; Wu, Yangjie; Wu, Yusheng; Tetrahedron Letters; vol. 61; 9; (2020);,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

Adding a certain compound to certain chemical reactions, such as: 38762-41-3, name is 4-Bromo-2-chloroaniline, belongs to chlorides-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 38762-41-3, COA of Formula: C6H5BrClN

General procedure: A dried tube, equipped with a magnetic stirred and a septum, 2-chloroanilines (1.0 mmol) was dissolved in DMSO(3 mL), and t-BuOK (3 mmol) was added. The mixture was stirred for 5 minutes, and thendimethylthiocarbamoyl chloride (1.2 mmol) and bis(dibenzylideneacetone) palladium (5 mol%) were added.the reaction mixture was then heated at 100 C and checked by TLC until the starting material was finished. Thereaction was cooled down to room temperature, and then quenched with sat. NH4Cl solution (5 mL) and extractedwith ethyl acetate, dried over anhydrous Na2SO4 and evaporated under vacuum. The residue was purified by flashcolumn chromatography to afford the desired product.

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-chloroaniline, other downstream synthetic routes, hurry up and to see.

Reference:
Article; Xu, Wan; Zeng, Meng-Tian; Liu, Min; Liu, Xing; Chang, Cai-Zhu; Zhu, Hui; Li, Yue-Sheng; Dong, Zhi-Bing; Chemistry Letters; vol. 46; 5; (2017); p. 641 – 643;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics