Month: May 2021

Adding a certain compound to certain chemical reactions, such as: 179897-90-6, name is 1,3-Dibromo-2-chloro-5-fluorobenzene, 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 179897-90-6, Safety of 1,3-Dibromo-2-chloro-5-fluorobenzene

l,3-Dibromo-2-chloro-5-fluorobenzene (400 mg, 1.39 mmol) dissolved in toluene (4 mL) and 2- methyltetrahydrofuran (1 mL) was treated with the triisopropyl borate (390 pL, 1.69 mmol). The mixture was cooled to -78 C in a dry ice/acetone bath and then n-butyllithium (2.5 M in hexanes, 680 pL, 1.70 mmol) was added slowly dropwise. The mixture was maintained at -78 C for 1 h and then slowly allowed to warm to room temperature. After stirring for 1 h, the reaction mixture was quenched by adding 1N HC1 solution, diluted with ethyl acetate and washed with water and brine. The organic layer was dried over sodium sulfate and filtered. The filtrate was concentrated and purified by ISCO silica gel chromatography to give (3-bromo-2-chloro-5-fluorophenyl)boronic acid.

At the same time, in my other blogs, there are other synthetic methods of this type of compound, 1,3-Dibromo-2-chloro-5-fluorobenzene, and friends who are interested can also refer to it.

Reference:
Patent; GILEAD SCIENCES, INC.; AKTOUDIANAKIS, Evangelos; CHO, Aesop; DU, Zhimin; GRAUPE, Michael; LAD, Lateshkumar Thakorlal; MACHICAO TELLO, Paulo A.; MEDLEY, Jonathan William; METOBO, Samuel E.; MUKHERJEE, Prasenjit Kumar; NADUTHAMBI, Devan; PARKHILL, Eric Q.; PHILLIPS, Barton W.; SIMONOVICH, Scott Preston; SQUIRES, Neil H.; WANG, Peiyuan; WATKINS, William J.; XU, Jie; YANG, Kin Shing; ZIEBENHAUS, Christopher Allen; (300 pag.)WO2019/204609; (2019); A1;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

Application of 54773-20-5, A common heterocyclic compound, 54773-20-5, name is 1,3-Dichloro-5-(trifluoromethyl)benzene, molecular formula is C7H3Cl2F3, 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 A: 2,6-dichloro-4-(trifluoromethyl)benzaldehyde A 2M n-BuLi solution (5.8 mL, 11.6 mmol) was added to a -78 C. THF solution (60 mL) of 1,3-dichloro-5-(trifluoromethyl)benzene (2.5 g, 11.6 mmol). After 45 min neat DMF (0.39 mL, 5.0 mmol) was added, and the resulting solution was allowed to warm to 0 C. gradually, quenched with NH4Cl solution, and extracted with diethyl ether. The combined extracts were dried (Na2SO4), concentrated, and purified via column chromatography to yield the title compound.

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; Chakravarty, Devraj; Greco, Michael; Shook, Brian; Xu, Guozhang; Zhang, Rui; US2012/302641; (2012); 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 59772-49-5 as follows. HPLC of Formula: C6H5BrClN

Benzofuran-3-ylboronic acid2-bromo-6-chloroaniline (189 g, 1100 mmol) was dissolved in toluene (Toluene), EtOH, H2O (400 mg, 400 mL). Pd (PPh3) 4 (58 g, 50 mmol) and NaHCO3 (252 g, 3000 mmol) were added thereto and refluxed for 4 hours. After completion of reaction, MC is extracted by cooling to room temperature. After drying over anhydrous MgSO4, the solvent is removed by rotary evaporator. Column chromatography (MC: Hx = 1: 3) was used to obtain the desired compound 461-5. (190 g, 91percent, brown oil)

According to the analysis of related databases, 59772-49-5, the application of this compound in the production field has become more and more popular.

Reference:
Patent; L Ti Material Co., Ltd.; Oh Han-guk; Lee Yun-ji; Ji Hye-su; Jeong Won-jang; Choi Jin-seok; Choi Dae-hyeok; (212 pag.)KR2019/33885; (2019); A;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

Adding a certain compound to certain chemical reactions, such as: 129482-45-7, name is 4-Benzyl-2-(chloromethyl)homomorpholine, 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 129482-45-7, name: 4-Benzyl-2-(chloromethyl)homomorpholine

EXAMPLE 54 (4-Benzyl-1,4-oxazepan-2-ylmethyl)-phenyl amine 80 Aniline (2.59 mL, 28.4 mmol) and NaI (4.06 g, 27.1 mmol) were added to a solution of 4-benzyl-2-chloromethyl-1,4-oxazepane (79) (6.49 g, 27.1 mmol) in n-butanol (68 mL, 0.4 M), and the reaction was heated to 110 C. until the reaction was judged complete by TLC (4 h). The reaction was cooled to room temperature, and water and CH2Cl2 were added. The organic layer was removed, and the aqueous layer was extracted with CH2Cl2 (2*). The combined organic extracts were dried over sodium sulfate, filtered and concentrated in vacuo to achieve (4-benzyl-1,4-oxazepan-2-ylmethyl)-phenyl amine 80, which was used without purification in the next reaction. 1H NMR (partial, CDCl3) 4.08-3.86 (3H, m), 3.80 (1H, d, J=13.3 Hz), 3.73 (1H, d, J =13.3 Hz), 3.22-3.05 (2H,.m), 2.95-2.70 (3H, m), 2.64 (1H, dd, J=13.6, 7.6 Hz), 2.1-1.9 (2H, m) ppm. 13C NMR (CDCl3) 148.33, 139.38, 129.28, 129.11, 128.46, 127.23, 117.44, 113.13, 76.70, 67.49, 62.92, 59.35, 54.76, 46.93, 30.75 ppm. LRMS: 296.68.

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; Cuny, Gregory D.; Shao, Liming; Hauske, James R.; Heffernan, Michele L.R.; Aquila, Brian M.; Wu, Xinhe; Wang, Fengjiang; Bannister, Thomas D.; US2002/16337; (2002); 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. 120758-03-4, name is 2-Chloro-3,5-dimethoxyaniline, A new synthetic method of this compound is introduced below., Application In Synthesis of 2-Chloro-3,5-dimethoxyaniline

Step 4 14.4 g of potassium isocyanate were dissolved at 10ØC in 450 ml of’acetone. 14.2 ml of benzoylchloride were added dropwise carefully. The white suspension was refluxed 10 minutes and then cooled again to 10ØC. A solution of 28 g of 2-chloro-3,5-dimethoxyaniline in 300 m! of acetone was then added and the obtained mixture refluxed over 3 h. 700 ml of water with ice were added and the aqueous phase was extracted with 3×600 ml of ethyl acetate. The organic phase was then dried over magnesium sulfate and concentrated. The brown residue was dissolved in 100 ml ethanol and refluxed together with 35 ml of an aqueous solution of potassium hydroxide. After 1 hour, 500 ml of water were added. Ethanol was distilled under reduced pressure. The brown solution was neutralized with 300 ml of an ammonium chloride solution and the solid which precipitated was filtered, washed with water and dried. 35 g of (2-chloro-3,5-dimethoxy-phenyl)-thiourea were obtained as a brown powder, m.p. 159-162ØC

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; Boehringer Ingelheim Pharma GmbH & Co.KG; EP1333028; (2003); A1;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

1303588-27-3, name is 7-Chloro-1,2,3,4-tetrahydro-1,8-naphthyridine, 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. Computed Properties of C8H9ClN2

Under a nitrogen atomosphere, 1 , 2, 3,4-tetrahydro- 1 ,8-naphthyridine (110; 1 .2g, 7. 12mmol) was dissolved in DME (40mL) along with , 3-(tri fluromethyl)-phenylboronic acid (2.03g, 1 0.68 mmol), Cs2C03 (4.64 g, 14.24 mmol) and Pd(dppf)Cl2 (297 mg, 0.356 mmol). The reaction mixture was stirred at 90 C overnight. The solid was filtrated. The filtration was then diluted with H2O and extracted with ethyl acetate. The combined organic layers were washed with brine, dried over Na2S04 and then concentrated in vacuo. The residue was purified by column chromatography to afford 7-(3-(trifluoromethyl)phenyl)- 1 ,2, 3 , 4-tetrahydro- 1 ,8-naphthyridine (111 ; 1.25g, 63%). MS (ESI) calcd for C sH nFs^ (m/z) 278.27.

The synthetic route of 1303588-27-3 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; SIRTRIS PHARMACEUTICALS, INC.; NG, Pui, Yee; BLUM, Charles; MCPHERSON, Lauren; PERNI, Robert, B.; VU, Chi, B.; AHMED, Mohammed, Mahmood; DISCH, Jeremy, S.; WO2011/59839; (2011); A1;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

Electric Literature of 1017777-58-0, 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. 1017777-58-0, name is 2-Chloro-6-fluoro-3-methoxyaniline belongs to chlorides-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below.

To a solution of 2-chloro-6-fluoro-3-methoxy-aniline (0.85 g, 4.84 mmol, 1.0 eq) in DCM (8 mL) at 0C was added BBr3 (6.06 g, 24.2 mmol, 5.0 eq). The mixture was stirred at room temperature under N2 overnight, then poured into ice-water. The pH of the solution was adjusted to pH 6 by addition of sat.NaHC03. The dichloro methane was removed under reduced pressure and the aqueous residue was extracted with EtOAc. The combined organic extracts were washed with brine, dried (Na2SC>4), filtered and evaporated in vacuo to give the title compound as a pale yellow solid (0.74 g, 95 %).LC-MS: m/z 162.0, 164.0 [M+H]1H NMR (400 MHz, DMSO-d6) delta 9.67 (s, 1H), 6.80 (dd, JJ= 8.9, 4.6 Hz, 1H), 5.20 (br s, 2H)

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-Chloro-6-fluoro-3-methoxyaniline, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; FOVEA PHARMACEUTICALS; FEUTRILL, John; LERICHE, Caroline; MIDDLEMISS, David; WO2013/37705; (2013); A2;,
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. 202865-57-4, name is 1-Bromo-2,5-dichloro-3-fluorobenzene, A new synthetic method of this compound is introduced below., Quality Control of 1-Bromo-2,5-dichloro-3-fluorobenzene

To a solution of 12a (0.450 g; 2.160 mmol) and NMP (5 mL) was added K2CO3 (0.896 g; 6.48 mmol) and 1-bromo-2,5-dichloro-3-fluoro-benzene (0.580 g; 2.38 mmol). The reaction was heated to 120 C. and monitored by TLC. After 8 h the reaction was cooled to RT and 10% HCl was added. The mixture was extracted with EtOAc and the combined extracts were washed with H2O and brine. The extracts were dried (Na2SO4), filtered and evaporated. The crude product was purified by SiO2 chromatography eluting with a gradient of hexane/EtOAc (100:0 to 60:40) to afford 146.

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; Roche Palo Alto LLC; US2005/239881; (2005); A1;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

Electric Literature of 1303588-27-3, 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. 1303588-27-3, name is 7-Chloro-1,2,3,4-tetrahydro-1,8-naphthyridine, This compound has unique chemical properties. The synthetic route is as follows.

The mixture of 7-chloro-l,2,3,4-tetrahydro-l,8-naphthyridine (110; 6.0 g, 35.7 mmol), Boc20 (15.6 g, 71.4 mmol) and 4-Dimethylaminopyridine (DM AP) (13.1 g, 107.1 mmol) in THF(200 mL) was stirred under reflux for overnight. TLC showed the reaction was complete and the mixture was poured into water. The organic layer was dried over anhydrous Na2S04, filtered and concentrated to give /er/-butyl 7-chloro-3,4-dihydro-l,8-naphthyridine-l(2H)-carboxylate (112; 8.74 g, 91%) as a white solid. MS (ESI) calcd for C13H17CIN2O2 (m/z) 268.74.

The chemical industry reduces the impact on the environment during synthesis 7-Chloro-1,2,3,4-tetrahydro-1,8-naphthyridine. I believe this compound will play a more active role in future production and life.

Reference:
Patent; SIRTRIS PHARMACEUTICALS, INC.; NG, Pui, Yee; BLUM, Charles; MCPHERSON, Lauren; PERNI, Robert, B.; VU, Chi, B.; AHMED, Mohammed, Mahmood; DISCH, Jeremy, S.; WO2011/59839; (2011); A1;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

Synthetic Route of 208186-78-1,Some common heterocyclic compound, 208186-78-1, name is 1,2-Dibromo-5-chloro-3-fluorobenzene, molecular formula is C6H2Br2ClF, 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.

Intermediate 10; 3-(2-Bromo-4-chloro-6-fluoro-phenyl)-5-methyl-[1,2,4]oxadiazole Step A: 2-Bromo-4-chloro-6-fluoro-benzaldehyde To a solution of 1,2-dibromo-5-chloro-3-fluoro-benzene (10 g, 34.68 mmol) in heptane (27 ml) was added THF (44 ml) and the mixture was cooled to -45 C. Then iPrMgCl (38.14 ml, 38.14 mmol, 1M solution in THF) was added dropwise to the reaction mixture maintaining the temperature between -40 C. to -45 C. The mixture was stirred for 30 minutes at -40 C. before DMF (13.4 ml, 173.4 mmol) was added dropwise to the reaction mixture maintaining the temperature between -45 C. to -20 C. After stirring for another 15 minutes at -20 C., the reaction mixture was poured into a mixture of 2N HCl (20 ml) and ether (50 ml) at 0 C. The organic layer was separated and the aqueous layer was extracted two times with ether. The combined organic layers were dried with Na2SO4 and evaporated in vacuo to obtain the title compound as yellow solid (7.8 g, 95%).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 1,2-Dibromo-5-chloro-3-fluorobenzene, its application will become more common.

Reference:
Patent; Aebi, Johannes; Binggeli, Alfred; Hertel, Cornelia; Konkar, Anish Ashok; Kuehne, Holger; Kuhn, Bernd; Maerki, Hans P.; Wang, Haiyan; US2012/165338; (2012); A1;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics