Author: Jessica.F

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 875664-41-8 as follows. Quality Control of 3-Bromo-4,5-difluoroaniline

Compound 99 A mixture of 3-(N-isopropylsulfamoyl)benzoic acid (2.3 g, 9.615 mmol), 3-bromo-4,5- difluoroaniline (2 g, 9.615 mmol) and DIPEA (5 mL) in CH2CI2 (30 mL) was cooled to 0C and HATU (4.39 g, 1 1.538 mmol) was added. The mixture was stirred for 2 hours at 20C. The mixture was washed with IN HC1 (30 mL) and brine (30 mL) and dried over Na2S04. The solvent was removed in vacuo. The residue was purified by silica gel column chromatography (gradient eluent: petroleum ether/ethyl acetate from 100/0 to 70/30) resulting in crude N-(3-bromo-4,5-difluorophenyl)-3-(N-isopropylsulfamoyl)- benzamide (4 g). A mixture of N-(3-bromo-4,5-difluorophenyl)-3-(N-isopropyl- sulfamoyl)benzamide (1 g, 2.308 mmol), methylboronic acid (1 g, 4.616 mmol), CS2CO3 (2.26 g, 6.924 mmol), 2-Dicyclohexylphosphino-2′,6′-dimethoxybiphenyl (95 mg, 0.231 mmol) and Tris(dibenzylideneacetone)dipalladium(0) (0.21 g, 0.231 mmol) in dioxane (15 mL) was heated by microwave irradiation for 40 minutes at 120C under N2 atmosphere. After cooling, the mixture was filtered through celite and the filtrate was evaporated to dryness. The obtained residue was purified by silca gel column chromatography (gradient eluent: petroleum ether/ethyl acetate from 100/0 to 70/30) and further purified by preparative high performance liquid chromatography over reversed phase C-18 (eluent: CH3CN in H20 (0.1% TFA) from 38% to 68%, v/v). The pure fractions were collected and half of the volatiles were removed in vacuo. The mixture was adjusted to pH=7 with Amberlite IRA-900 (OH) anionic exchange resin and the resin was filtered off. The organic solvent was concentrated in vacuo and the aqueous layer was lyophilized to dryness. The obtained product was further purified by silica gel chromatography (gradient eluent: petroleum ether/ethyl acetate from 100/0 to 70/30) resulting in compound 99 (190 mg). Method A; Rt: 6.09 min. m/z : 369.2 (M+H)+ Exact mass: 368.1, 1H NMR (400 MHz, CHLOROFORM- ) delta ppm 8.35 (1 H, t, J=1.5 Hz), 8.09 – 8.17 (2 H, m), 8.04 (1 H, dt, J=8.0, 1.5 Hz), 7.66 (1 H, t, J=8.0 Hz), 7.54 (1 H, ddd, J=11.5, 6.5, 3.0 Hz), 7.14 – 7.22 (1 H, m), 4.72 (1 H, d, J=8.0 Hz), 3.43-3.60 (1 H, m), 2.32 (3 H, d, J=2.0 Hz), 1.10 (6 H, d, J=6.5 Hz).

According to the analysis of related databases, 875664-41-8, the application of this compound in the production field has become more and more popular.

Reference:
Patent; JANSSEN R&D IRELAND; LAST, Stefaan Julien; RABOISSON, Pierre Jean-Marie Bernard; ROMBOUTS, Geert; VANDYCK, Koen; VERSCHUEREN, Wim Gaston; WO2014/33170; (2014); A1;,
Bromide – Wikipedia,
bromide – Wiktionary

Reference of 41825-73-4, 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. 41825-73-4 name is 2-Bromo-4,6-dimethylaniline, 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.

General procedure: 2-iodoaniline (0.5 mmol) or 2-bromoaniline (0.5 mmol), complex 1 (0.05mmol), K2CO3 (1 mmol), (n-Bu)4NBr (0.1 mmol) and water (10 mL) were added to a sealed tube. The reaction mixture was stirred at 120oC for 30 h, then cooled to room temperature and then extracted with ethyl acetate. The organic layer was dried over anhydrous Na2SO4 and the solvent was then removed under reduced pressure. The product was finally obtained by column chromatography on silica gel.

At the same time, in my other blogs, there are other synthetic methods of this type of compound, 2-Bromo-4,6-dimethylaniline, and friends who are interested can also refer to it.

Reference:
Short Survey; Yu, Lintao; Zhou, Xiangge; Wu, Di; Xiang, Haifeng; Journal of Organometallic Chemistry; vol. 705; (2012); p. 75 – 78;,
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. 627526-90-3, name is 1-Bromo-3-(difluoromethyl)-5-fluorobenzene, This compound has unique chemical properties. The synthetic route is as follows., HPLC of Formula: C7H4BrF3

(B) To a solution of 1-bromo-3-(difluoromethyl)-5-fluorobenzene (8.6 g, 38.56 mmol, I eq) and DIPEA(13.44 ml, 77.12 mmol, 2 eq) in 1,4-dioxane (150 ml) was added PMB-SH (5.89 ml, 42.42 mmol, 1.1 eq).The mixture was degassed for 10 mm, and Xantphos (1.56 g, 2.69 mmol, 0.07 eq), followed by Pd2(dba)3 (1.0 g, 1.15 mmol, 0.03 eq) were added. The mixture was again degassed for 10 mm. The resulting RM was heated to 90 C and stirred for 2 h under Ar. The RM was filtered through celite and the filtrate concentrated to yield the crude product, which upon flash chromatography afforded 1 -bromo-3-(difluoro-methyl)-5-fluorobenzene (10 g, 87%).

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 627526-90-3.

Reference:
Patent; GRUeNENTHAL GMBH; SCHUNK, Stefan; REICH, Melanie; JAKOB, Florian; DAMANN, Nils; HAURAND, Michael; KLESS, Achim; ROGERS, Marc; SUTTON, Kathy; WO2015/158427; (2015); A1;,
Bromide – Wikipedia,
bromide – Wiktionary

Adding a certain compound to certain chemical reactions, such as: 35354-37-1, name is 1-Bromo-5-methylhexane, 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 35354-37-1, Safety of 1-Bromo-5-methylhexane

(a) Methyl 1-(5-methylhexyl)cyclopentanecarboxylate To a solution of methyl cyclopentanecarboxylate (300 mg, 2.3 mmol) in THF (20 ml) at -78¡ã C. was added LHMDS (4.6 mL, 4.6 mmol) and stirred for 30 min, and followed by 1-bromo-5-methylhexane (626 mg, 3.5 mmol). The mixture was stirred from -78¡ã C. to rt over 16 hr, before 30 ml of H2O was added and then was extracted with CH2Cl2 (2*30 mL). The combined extracts were washed with water, dried over MgSO4, filtered and concentrated, then purified using flash chromatography to give an oil (110 mg, 21percent). MS [M+H]+333.

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; Yang, Michael G.; Liu, Hong; US2002/61874; (2002); 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. 627526-90-3, name is 1-Bromo-3-(difluoromethyl)-5-fluorobenzene, This compound has unique chemical properties. The synthetic route is as follows., HPLC of Formula: C7H4BrF3

Intermediate CZ: 2-(3-(difluoromethyl)-5-fluorophenyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane A solution of PdCl2(dppf)-DCM adduct (0.399 g, 0.489 mmol), bis(pinacolato) diboron (2.73 g, 10.76 mmol), 1-bromo-3-(difluoromethyl)-5-fluorobenzene (Oakwood Chemicals, 2.200 g, 9.78 mmol) and potassium acetate (3.84 g, 39.1 mmol) in 35 mL DMF was heated to 100 C. overnight. The reaction mixture was then diluted with DCM and was washed with water. The organics were dried over MgSO4 and concentrated. Purification of the crude residue by silica gel column chromatography (0-70% EtOAc/heptane) gave 2-(3-(difluoromethyl)-5-fluorophenyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane (1.64 g, 6.03 mmol, 61.6% yield) as a yellow oil. 1H NMR (Acetone) ?: 7.72-7.78 (m, 1H), 7.44-7.58 (m, 2H), 6.99 (s, 1H), 1.32-1.43 (m, 12H).

According to the analysis of related databases, 627526-90-3, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Amgen Inc.; Weiss, Matthew; Boezio, Alessandro; Boezio, Christiane; Butler, John R.; Chu-Moyer, Margaret Yuhua; Dimauro, Erin F.; Dineen, Thomas; Graceffa, Russell; Guzman-Perez, Angel; Huang, Hongbing; Kreiman, Charles; La, Daniel; Marx, Isaac E.; Milgrim, Benjamin Charles; Nguyen, Hanh Nho; Peterson, Emily; Romero, Karina; Sparling, Brian; US9212182; (2015); B2;,
Bromide – Wikipedia,
bromide – Wiktionary

Related Products of 41825-73-4, These common heterocyclic compound, 41825-73-4, name is 2-Bromo-4,6-dimethylaniline, 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.

Step 1: Synthesis of 3,5-dimethyl-6-phenanthridinamine Added together 2-cyanophenylboronic acid pinacol ester (13.7 g, 60 mmol), 2-bromo-4,6-dimethylaniline (10.0 g, 50 mmol), tetrakis(triphenylphosphine)palladium(0) (2.3 g, 2.0 mmol) and potassium carbonate (18.6 g, 138.21 mol) to a 125 mL of a 95/5 mixture of toluene/methanol. The solvents were degassed and the reaction mixture heated to reflux for 48 hours. After cooling, the reaction mixture was vacuum filtered and the organics evaporated and crude product was purified using silica gel column chromatography treated with triethylamine and 1:9 ethyl acetate and methylene chloride mixture as the eluants. The pure product was collected and concentrated to give 3,5-dimethyl-6-phenanthridinamine (9.1 g, 82% Yield).

The synthetic route of 41825-73-4 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Universal Display Corporation; Knowles, David; Lin, Chun; Mackenzie, Peter; Tsai, Jui-Yi; Walters, Robert W.; Beers, Scott; Brown, Cory S.; Yeager, Walter; (85 pag.)US9281483; (2016); B2;,
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. 90562-10-0, name is 1-Bromo-4-(3-bromopropyl)benzene, A new synthetic method of this compound is introduced below., HPLC of Formula: C9H10Br2

Example 139. l-[3-(4~Bromo-phenyl)-propyn-pyrrolidine C80); [0324] To a solution of compound 79 described in Example 138 (3.5 g, 13 mmol) in dioxane (40 mL) was added pyrrolidine (2.1 mL, 25 mmol) followed by cesium carbonate (8.2 g, 25 mmol). The mixture was stirred at room temperature for 15 h and poured into water. The mixture was extracted with ethyl acetate and the organic layer separated, EPO washed with brine, dried over Na2SO4 and filtered. The filtrate was concentrated and the residue purified by flash chromatography on silica gel (10% MeOH/DCM to 25% MeOH and 2% TEA/DCM) to afford the title compound (1.8 g, 53%) as a pale orange oil.[0325] 1H NMR (500 MHz, DMSO-d6): delta 1.60-1.65 (m, 6H), 2.35 (t, J= 7.3 Hz, 2H), 2.35-2.43 (m, 4H), 2.57 (t, J= 7.7 Hz, 2H), 7.16 (d, J= 8.3 Hz, 2H), 7.44 (d, J= 8.4 Hz, 2H).

The synthetic route of 90562-10-0 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; TARGEGEN, INC.; WO2006/101977; (2006); A2;,
Bromide – Wikipedia,
bromide – Wiktionary

Related Products of 1435-54-7, 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. 1435-54-7, name is 1,3-Dibromo-2-fluorobenzene belongs to bromides-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below.

A stirred solution of 1,3-dibromo-2-fluorobenzene (15.95 g, 62.82 mmol, 1.0 equiv.) in anhydrous THF (100 mL) is cooled to -78 C. n-Butyllithium (1.6 N, 47.1 mL, 75.36 mmol, 1.2 equiv.) is added dropwise and the resulting mixture is stirred for 30 min at -78 C. D-2b (10.00 g, 62.82 mmol, 1.0 equiv.) dissolved in THF (40 mL) is slowly added. After complete conversion, saturated aqueous ammonium chloride is added. The aqueous layer is extracted with EtOAc, the organic layers are combined, dried over Na 2SO 4 and concentrated under reduced pressure. The crude product is purified by chromatography on silica gel (gradient elution: 10% to 20% ethyl acetate in petroleum ether) yielding the desired product D-3b.

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, 1,3-Dibromo-2-fluorobenzene, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; Boehringer Ingelheim International GmbH; RAMHARTER, Juergen; KOFINK, Christiane; STADTMUELLER, Heinz; WUNBERG, Tobias; HOFMANN, Marco Hans; BAUM, Anke; GMACHL, Michael; RUDOLPH, Dorothea Ingrid; SAVARESE, Fabio; OSTERMEIER, Markus; FRANK, Markus; GILLE, Annika; GOEPPER, Stefan; SANTAGOSTINO, Marco; WIPPICH, Julian; (175 pag.)US2019/194192; (2019); A1;,
Bromide – Wikipedia,
bromide – Wiktionary

Related Products of 268733-18-2,Some common heterocyclic compound, 268733-18-2, name is 4-Bromo-3,5-bis(trifluoromethyl)aniline, molecular formula is C8H4BrF6N, 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.

synthesis of ethyl 5 -(4-amino-2, 6-bis(trifluoromethyl)phenyl)furan-2-carboxylate (143): 4-Bromo-3,5-bis(trifluoromethyl)aniline (142; 8 g, 26 mmol), 5- (ethoxycarbonyl)furan-2-ylboronic acid (7.2 g, 39 mmol), catalyst (2.1 g, 2.6 mmol) and K3P04 (16.5 g, 78 mmol) were added to a mixture of H20 (156 mL) and THF (300 mL). The mixture was degassed and stirred at room temperature for 2 h, extracted with EtOAc (300 mL X 2). The combined organic solvents were concentrated under reduced pressure and purified by silica gel chromatography (10-30% EtOAc/petroleum ether) to give 4.6 g of ethyl 5-(4- amino-2, 6-bi s(trifluoromethyl)phenyl)furan-2-carboxylate 143 as brown solid (48% yield). LCMS: m/z 368.0 [M+H], tR = 1.91 mm

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-bis(trifluoromethyl)aniline, its application will become more common.

Reference:
Patent; KARYOPHARM THERAPEUTICS INC.; BALOGLU, Erkan; SHACHAM, Sharon; SENAPEDIS, William; (153 pag.)WO2017/31213; (2017); A1;,
Bromide – Wikipedia,
bromide – Wiktionary

Synthetic Route of 113899-55-1, A common heterocyclic compound, 113899-55-1, name is 1-(2-Bromophenyl)ethylamine, molecular formula is C8H10BrN, 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.

(1) Di-t-butyl dicarbonate (1.26 ml) was added to a solution of 1-(2-bromophenyl)ethanamine (1.0 g) obtained by the method described in the literature (Tetrahedron Letters, 2007, vol. 48, p.4589) in chloroform (10 ml), and the resulting mixture was stirred at room temperature for 2 hours. The reaction mixture was concentrated under reduced pressure, and the resulting residue was purified by silica gel column chromatography (chloroform:methanol = 50:1) to obtain a protected compound (1.52 g).

The synthetic route of 113899-55-1 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Taisho Pharmaceutical Co., Ltd.; Meiji Seika Kaisha, Ltd.; EP2287173; (2011); A1;,
Bromide – Wikipedia,
bromide – Wiktionary