Author: Jessica.F

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

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

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

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

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

Reference of 25186-47-4, A common heterocyclic compound, 25186-47-4, name is 3,5-Dichlorotoluene, molecular formula is C7H6Cl2, 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.

To a stirred solution of l ,3-dichloro-5-methylbenzene (2.0 g, 12.4 mmol) in THF (20 mL) was added n-BuLi (2.0 M in hexane, 9.3 mL, 18.6 mmol) at -78 C dropwise over a period of 10 miri and mixture was stirred at -78 C for 30 min. A dry-ice was added to the reaction mixture slowly and the mixture was stirred at the same temperature for 20 min. Thereafter, the reaction mixture was slowly warmed to room temperature, quenched with 6 M HC1 (10 mL) and extracted with EtOAc (2 x 30 mL). The combined organic layers were washed with water (50 mL), brine (50 mL), dried over anhydrous Na2S04 and concentrated under reduced pressure to get compound Al 11 -1 (1.1 g, 44%) as a white solid.

The synthetic route of 25186-47-4 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; TEIJIN PHARMA LIMITED; AMGEN INC.; BECK, Hilary Plake; BOOKER, Shon Keith; BREGMAN, Howard; CEE, Victor J.; CHAKKA, Nagasree; CUSHING, Timothy D.; EPSTEIN, Oleg; FOX, Brian M.; GEUNS-MEYER, Stephanie; HAO, Xiaolin; HIBIYA, Kenta; HIRATA, Jun; HUA, Zihao; HUMAN, Jason; KAKUDA, Shinji; LOPEZ, Patricia; NAKAJIMA, Ryota; OKADA, Kazuhisa; OLSON, Steven H.; OONO, Hiroyuki; PENNINGTON, Lewis D.; SASAKI, Kosuke; SHIMADA, Keiko; SHIN, Youngsook; WHITE, Ryan D.; WURZ, Ryan P.; YI, Shuyan; ZHENG, Xiao Mei; WO2015/129926; (2015); A1;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

These common heterocyclic compound, 7051-15-2, name is 2-Chloro-1,3-dimethoxybenzene, 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. Recommanded Product: 2-Chloro-1,3-dimethoxybenzene

The 13.9g acetophenone (115.6mmol), 10.9g chlorobenzene (96.7mmol), 11.1g sodium tert-butoxide (115.6mmol) and 0.35g azacarbene imine palladium catalyst added in Example 6 9.8g p-cyanoacetophenone (67.3mmol), 9.6g 2,6-dimethoxychlorobenzene (56.1mmol), 6.5g sodium tert-butoxide (60mmol) and 0.2g azacyclocarbene imines The palladium catalyst and 60 mL of 1,4-dioxane solvent were not changed under other conditions, and the target product was obtained 14.0 g, and the isolated yield was 89%.In Example 6, the 0.35g nitrogen heterocyclic carbene imine palladium catalyst A1 was replaced with 0.24g A2, 0.29g A3, 0.34g A4, 0.24g A5, and the separation yields were 98%, 96%, 90%, 90%.

The synthetic route of 2-Chloro-1,3-dimethoxybenzene has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Shanghai Chemical Institute Co., Ltd.; Lu Huiyang; Shen An; Cao Yucai; Li Yongqing; Ni Chen; Hu Yucai; (14 pag.)CN110818545; (2020); A;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

Application of 21402-26-6, 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. 21402-26-6, name is 4-Bromo-3-chloroaniline belongs to chlorides-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below.

Example 1 Preparation of N,N-Dipentyl-4-bromo-3-chloroaniline (1). 1-Bromopentane (0.42 mL, 3.4 mmol) was added to a mixture of 4-bromo-3-chloroaniline (200 mg, 0.9 mmol) and potassium carbonate (199 mg, 1.4 mmol) in DMF (20 mL) and the reaction was heated to 13 0~~C overnight. The mixture was cooled, diluted with water (20 mL) and extracted with petroleum ether (3*25mL). The combined organic extracts were dried over sodium sulfate, filtered and concentrated under reduced pressure. The residue was purified via flash column chromatography using 9:1 petroleum ether:ethyl acetate as eluent to give N,N-Dipentyl-4-bromo-3-chloroaniline (1) (332 mg, 68%). 1H-NMR (CDCI3) 67.02 (d, IH, ArH); 3.12 (t, 4H, 2*NCH2); 0.95 (t, 6H, 2*CH3). MS; 347 (M+H).

The synthetic route of 4-Bromo-3-chloroaniline has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Oxford Glycosciences (UK) Ltd.; US6262263; (2001); B1;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

Adding a certain compound to certain chemical reactions, such as: 320-50-3, name is 1,4-Dichloro-2-(trifluoromethyl)benzene, 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 320-50-3, Quality Control of 1,4-Dichloro-2-(trifluoromethyl)benzene

Similarly, 4-(2-trifluoromethyl-4-chlorophenoxy)benzene is prepared by following the same procedure but using 1,4-dichloro-2-trifluoromethylbenzene in place of 1,2-dichloro-4-trifluoromethylbenzene.

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, 1,4-Dichloro-2-(trifluoromethyl)benzene, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; Chevron Research Company; US4287213; (1981); 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. 102170-53-6, name is 4-Bromo-5-chloro-2-methoxyaniline, A new synthetic method of this compound is introduced below., SDS of cas: 102170-53-6

Intermediate 7: 2-Amino-5-bromo-4-chlorophenol 4-Bromo-5-chloro-2-methoxyaniline (Intermediate 6, 10g, 42.3 mmol) in DCM (200 mL) was cooled to 0 C. Boron tribromide (21 .2 g, 84.6 mmol) was added drop-wise over 30 min, the reaction mixture was stirred at 0 C for 1 h and then at room temperature for 14 h. The reaction mixture was poured into ice water, sodium hydrogen carbonate was added until pH >7 and aqueous layer was extracted with ethyl acetate (300 mL x 3). The organic phase was dried over magnesium sulphate and the solvent removed under vacuum to give 2-amino-5-bromo-4-chlorophenol as a red solid (8.4 g, 89%, used without further purification for the next step). LCMS (A): Rt 1.46 min, MH+ 222/224.

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; GLAXOSMITHKLINE INTELLECTUAL PROPERTY DEVELOPMENT LIMITED; BOUILLOT, Anne Marie Jeanne; MIRGUET, Olivier; LIDDLE, John; WALKER, Ann, Louise; WO2015/91647; (2015); A1;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics