Category: chlorides-buliding-blocks

Electric Literature of 467435-07-0,Some common heterocyclic compound, 467435-07-0, name is 4-Bromo-2-chlorobenzotrifluoride, molecular formula is C7H3BrClF3, 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.

Into a glass reaction vessel equipped with a stirrer and having a capacity of 250 mL,7.2 g (68.0 mmol) of sodium carbonate,2.6 g (20.4 mmol) of 2-thiopheneboronic acid,4-Bromo-2-chlorobenzotrifluoride 2.5 mL(17.0 mmol), dehydrated toluene 102 mL, dehydrated ethanol 51 mL,And 2.0 g (1.7 mmol) of tetrakistriphenylphosphine palladium,And the mixture was reacted at 80 C. for 16 hours.Water was added to the reaction product, and the mixture was extracted with methylene chloride.After drying with magnesium sulfate and distilling off the solvent under reduced pressure, purification by silica gel column chromatography (hexane) gave 4.4 g of compound (C11-c) as a white solid.

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-chlorobenzotrifluoride, its application will become more common.

Reference:
Patent; Ube Industries Ltd; Tanaka, Yasuhiro; Homma, Takashi; (66 pag.)JP2018/168138; (2018); A;,
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 25186-47-4 as follows. Quality Control of 3,5-Dichlorotoluene

(1) device: Referring to Figure 2 to determine the connection of the tubular reactor, the pipeline type is:(3a + 3d) DC-channel+ enhanced hybrid round cake rectangular flat pipe,Pipe diameter and volume based on the flow rate and reaction to determine the residence time,Heat transfer medium for thermal oil.(2) 6.06 g of cobalt acetate and 6.06 g of sodium molybdate were dissolved respectively200ml3,5 – dichloro toluene and200ml acetic acid to form a mixed solution,In this case, n (cobalt acetate): n (3,5-dichlorotoluene) = 0.015: 1,6.06 g of sodium bromide was dissolved in 20% H2O2 to form a H2O2-acetic acid solution, where n (sodium bromide): n (3,5-dichlorotoluene) = 0.015: 1,3,5-dichlorotoluene-acetic acid Solution and andH2O2-acetic acid solution respectively to 8.33ml / min andThe flow rate of 16.67 ml / min was injected into the tubular reactor which was continuously heat-exchanging by the constant current pump, at this time, n (H2O2): n (3,5-dichlorotoluene) = 2:Using the microchannel reactor of Figure 2,The reaction temperature was controlled at 105 C and the residence time was 600 s.The outlet was cooled at 0 C and the reaction quenched with dichloromethane.After GC analysis, 3,5-dichlorotoluene conversion rate of 60.8%The yield of 3,5-dichlorobenzaldehyde was 39.2%.

According to the analysis of related databases, 25186-47-4, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Changzhou University; Yan Shenghu; Jiang Xin; Zhang Yue; Liu Jianwu; Shen Jiefa; Ma Xiaoming; Chen Daixiang; Gu Shunlin; Ni Fengchao; Li Yanfei; Wang Qiuhong; Chen Mingzhu; Wei Jin; Wu Fei; Zhang Yongchao; (9 pag.)CN106588606; (2017); A;,
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 81067-41-6 as follows. HPLC of Formula: C6H2Br2Cl2

Insert the 1,3-dibromo-2,5-dichlorobenzene (3.0g, 0.010mol) in pyridin-3-ylboronic acid (2.9g, 0.024mol) by synthesis by the same method used in Preparation Example 1-7 to give the intermediate 20-1> 2.1g (70% yield).

According to the analysis of related databases, 81067-41-6, the application of this compound in the production field has become more and more popular.

Reference:
Patent; PNH TECH; HYUN, SEO YONG; JUNG, SUNG OUK; KIM, IK HWAN; (101 pag.)KR2016/40826; (2016); A;,
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. 90390-33-3, name is 3-Chloro-5-fluorobenzylamine, A new synthetic method of this compound is introduced below., Recommanded Product: 90390-33-3

159 mg of 3-chloro-5-fluorobenzylamine (1 mmol) was weighed into a dry 50 mL eggplant-shaped reaction flask, and 15 mL of dichloromethane was added.The mixture was stirred until the substrate was completely dissolved. After adding 200 muL of triethylamine, a solution of 194 mg of octanoyl chloride (1.2 mmol in a suitable amount of dry dichloromethane) was slowly added dropwise under an ice bath at 0 to 5 C.After the completion of the dropwise addition, the TLC tracking and monitoring were carried out at room temperature, and when the raw materials disappeared, 20 mL of saturated sodium hydrogencarbonate was sequentially used.The water and the saturated aqueous NaCl solution were each washed three times and dried over anhydrous sodium sulfate.After vacuum distillation under reduced pressure, silica gel column chromatography was used to give N-(3-chloro-5-fluorobenzyl)octanamide.

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; Shanghai Shidande Biological Co., Ltd.; Shanghai Shidande Criterion Technology Services Co., Ltd.; Qian Yong; Xin Zhenqiang; Shu Yaping; Zhang Tianyong; Xie Tianpei; (11 pag.)CN108503559; (2018); A;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

Adding a certain compound to certain chemical reactions, such as: 7051-15-2, name is 2-Chloro-1,3-dimethoxybenzene, 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 7051-15-2, Quality Control of 2-Chloro-1,3-dimethoxybenzene

General procedure: A typical procedure is given for the reaction represented by Entry 8 in Table 1. Ligand 2e (6 mg, 0.01 mmol), Pd2(dba)3 (5 mg, 0.005 mmol), 2-methylnaphthyl-1-boronic acid (223 mg, 1.2 mmol), Cs2CO3 (975 mg, 3 mmol) were introduced to a flask under N2 gas. 1-bromo-2-methylnaphthalene (221 mg, 1 mmol) was added into the flask, followed by addition of THF (5 ml) by a syringe. The mixture was stirred under reflux for 24 h, under ambient pressure of N2. The solvent was then removed under reduced pressure. The resultant residual mixture was diluted with H2O (10 ml) and Et2O (10 ml), followed by extraction twice with Et2O. The organic extract was collected and stripped of solvent under vacuum. The product was isolated by column chromatography on silica eluting with hexane/ethyl acetate to give 276 mg (98%) of 2,2′-dimethyl-1-1′-binaphthalene as a solid, which was verified by GC/MS.

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

Reference:
Conference Paper; Teo, Shihui; Weng, Zhiqiang; Hor, T.S. Andy; Journal of Organometallic Chemistry; vol. 696; 17; (2011); p. 2928 – 2934;,
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. 69411-05-8, name is 3-Chloro-5-trifluoromethylaniline, A new synthetic method of this compound is introduced below., name: 3-Chloro-5-trifluoromethylaniline

[0092] Synthesis of trans-V-tert-buty 4′-ethyl 3-((3-chloro-5-(trifluoromethyl) phenyl)amino)-2-oxo-[l,3′-bipiperidine]- ,4′-dicarboxylate. A 1.0 M solution of lithium bis(trimethyldisilyl)amide in THF (13 mL, 12 mmol, 2.0 equiv) was added through an addition funnel at 10-15 C to a solution of 3-chloro-5-(trifluoromethyl)aniline (15 g, 78 mmol, 1.2 equiv) in THF (13 mL). The mixture was allowed to stir at room temperature for 20 min and a solution of crude trans- -tert-butyl-4′-ethyl-3-iodo-2-oxo-[l,3′-bipiperidine]- ,4′- dicarboxylate 9 (3.7 g, 65 mmol, 1.0 equiv) in THF (13 mL) was added through an addition funnel at 10-15 C over 30 min. After addition, the reaction was allowed to stir at the temperature for 30 min. Upon completion, the reaction was cooled to 5 C and quenched slowly with water (10 mL), keeping the temperature below 20 C. The quenched reaction was extracted with EtOAc (2 x 30 mL). The combined organic layers were washed with saturated brine (30 mL), dried (Na2S04), filtered, and concentrated in vacuo. The resulting crude product was purified over silica gel eluting with a gradient of 10% to 75%> of EtOAc in heptanes to give the desire product 10. ESI- MS (M+H-56) +: 463.1. 1H NMR (400 MHz, CDC13) delta: 6.92 (s, 1H), 6.71-6.69 (m, 2H), 4.17- 4.06 (m, 4H), 3.78-3.68 (m, 2H), 3.46-3.36 (m, 3H), 3.23-3.07 (m, 2H), 2.73-2.65 (m, 1H), 2.44- 2.37 (m, 1H), 2.03-1.85 (m, 3H), 1.71-1.61 (m, 2H), 1.46 (s, 9H), 1.27-1.19 (m, 3H).

The synthetic route of 69411-05-8 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; BIOGEN IDEC MA INC.; SUNESIS PHARMACEUTICALS, INC.; HOPKINS, Brian T.; CONLON, Patrick; CHAN, Timothy R.; JENKINS, Tracy J.; CAI, Xiongwei; HUMORA, Michael; SHI, Xianglin; MILLER, Ross A.; THOMPSON, Andrew; WO2013/185084; (2013); A1;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

Synthetic Route of 1298031-94-3, 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. 1298031-94-3, name is 8-Bromo-6-chloro-2-methylimidazo[1,2-b]pyridazine belongs to chlorides-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below.

8-Bromo-6-chloro-2-methylimidazo[l,2-b]pyridazine (1 g, 4.1 mmol, prepared according to Example 43) was combined with propylmagnesiumbromide (660 mg, 4.5 mmol) and iron(III) 2,4- pentanedionate (140 mg, 0.4 mmol) in dry THF (30 mL). The mixture was stirred at 50 C for 1 h under N2. The mixture was partitioned between EtOAc and H20. The organic layer was washed with brine, dried over Na2S04, filtered and concentrated. The residue was chromatographed on silica gel, eluting with 20-30% EtOAc in petroleum ether to yield 6-chloro-2-methyl-8- propylimidazo[l,2-b]pyridazine (230 mg, 27%). MS m/z 210.0, 212.0 [M+H]+.

The synthetic route of 8-Bromo-6-chloro-2-methylimidazo[1,2-b]pyridazine has been constantly updated, and we look forward to future research findings.

Reference:
Patent; PTC THERAPEUTICS, INC.; WOLL, Matthew, G.; AMEDZO, Lukiana; BABU, Suresh; BARRAZA, Scott, J.; BHATTACHARYYA, Anuradha; KARP, Gary, Mitchell; MAZZOTTI, Anthony, R.; NARASIMHAN, Jana; PATEL, Jigar; TURPOFF, Anthony; XU, Zhenrong; (251 pag.)WO2018/226622; (2018); A1;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

Reference of 21745-41-5, 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. 21745-41-5, name is 1,2-Diamino-3-chlorobenzene belongs to chlorides-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below.

Synthesis of 4-chloro-lH-benzo[d]imidazol-2-amine; [00402] Cyanogen bromide was added to a solution of 3-chlorobenzene- 1 ,2- diamine (0.81 g, 0.570 mmol) in acetonitrile (10 mL) and water (2 ml) at 0 0C. The reaction mixture was allowed to warm to room temperature and stirred for 14 hours. The reaction was quenched with saturated aqueous sodium hydrogen carbonate (50 ml) and shaken. The resulting solid was filtered off, was washed with water and dried at reduced pressure to 0.49 g of 4-chloro-lH-benzo[d]imidazol-2-amine (yield, 49%). MS (EI): 168 (MH+).

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, 1,2-Diamino-3-chlorobenzene, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; EXELIXIS, INC.; WO2008/42282; (2008); A2;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

These common heterocyclic compound, 120758-03-4, name is 2-Chloro-3,5-dimethoxyaniline, 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. Product Details of 120758-03-4

Example 10 Synthesis of 1-(2-chloro-3,5-dimethoxyphenyl)-6-sec-butyl-3-methyl-2-phenyl-4(1H)-pyridinone (Compound 131) To 500 ml of xylene were added 5.2 g of 2,6-dimethyl-1-phenyl-1,3,5-octanetrione, 5.2 g of 2-chloro-3,5-dimethoxyaniline and 5.7 g of p-toluenesulfonic acid, followed by reflux the reaction mixture with a Dean-Stark trap for 1 hour. After cooling, the reaction mixture was poured into water, followed by addition of 200 ml of chloroform. After extraction with chloroform, the organic layer was washed first with a 10% aqueous solution of sodium sulfate and then with 10% hydrochloric acid. After washing the solution in chloroform further with water, it was dried over anhydrous sodium sulfate. Subsequent to removal of the sodium sulfate, the solvent was distilled off and the residue was purified by column chromatography on silica gel (eluent: 1:1 mixed solvent of n-hexane and chloroform). The resulting crystals were recrystallized from acetone, thereby affording 2.3 g of 1-(2-chloro-3,5-dimethoxyphenyl)-6-sec-butyl-3-methyl-2-phenyl-4(1H)-pyridinone having a melting point of 220-221 C.

The synthetic route of 2-Chloro-3,5-dimethoxyaniline has been constantly updated, and we look forward to future research findings.

Reference:
Patent; KUMIAI CHEMICAL INDUSTRY CO., LTD.; IHARA CHEMICAL INDUSTRY Co., Ltd.; EP304057; (1989); A2;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

Application of 1298031-94-3,Some common heterocyclic compound, 1298031-94-3, name is 8-Bromo-6-chloro-2-methylimidazo[1,2-b]pyridazine, molecular formula is C7H5BrClN3, 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 mixture of 8-bromo-6-chloro-2-methyl-imidazo[1,2-b]pyridazine (100 mg, 0.41 mmol, 1.0 eq.), benzyl alcohol (89 mg, 0.085 mL, 0.81 mmol, 2.0 eq.) and Cs2CO3 (400 mg, 1.2 mmol, 3.0 eq.) in acetonitrile (1.0 mL) was stirred at 88 C overnight, then cooled, diluted with ethyl acetate and filtered through Celite. The filtrate was concentrated and purified over silica with ethyl acetate in CH2Cl2 (0 to 10% gradient) to give 8-benzyloxy-6-chloro-2-methyl-imidazo[1,2-b]pyridazine (81 mg, 73% ). 1H NMR (CDCl3) d: 7.62 (d, J= 0.6 Hz, 1H), 7.46 – 7.53 (m, 2H), 7.36 – 7.44 (m, 3H), 6.41 (s, 1H), 5.39 (s, 2H), 2.48 (d, J= 0.6 Hz, 3H).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 8-Bromo-6-chloro-2-methylimidazo[1,2-b]pyridazine, its application will become more common.

Reference:
Patent; PTC THERAPEUTICS, INC.; ZHANG, Nanjing; BABU, Suresh; BARRAZA, Scott J.; BHATTACHARYYA, Anuradha; CHEN, Guangming; KARP, Gary Mitchell; KASSICK, Andrew J.; MAZZOTTI, Anthony R.; MOON, Young-Choon; NARASIMHAN, Jana; SYDORENKO, Nadiya; TURPOFF, Anthony; WOLL, Matthew, G.; YAN, Wuming; (0 pag.)WO2020/5877; (2020); A1;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics