Tag: M.W=200-300

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. 54932-72-8, name is 4-Bromo-1-chloro-2-methylbenzene, A new synthetic method of this compound is introduced below., name: 4-Bromo-1-chloro-2-methylbenzene

A mixture of 3-(3-chlorophenyl)-1H-pyrazole (5.3 g, 29.8 mmol) (prepared according to the method given in European Patent Publication EP 538156), salicylaldoxime (0.58 g, 4.25 mmol), 5-bromo-2-chlorotoluene (2.8 g, 21.3 mmol), copper oxide (0.15 g, 1.06 mmol) and cesium carbonate (11.8 g, 36.2 mmol) in 20 mL of Af N-dimethylformamide was heated at 140 C overnight and then allowed to cool to room temperature. The resulting suspension was filtered and the filtrate was concentrated under reduce pressure. The resulting residue was purified by medium pressure liquid chromatography (2 to 10% gradient of ethyl acetate in hexanes as eluant) to give the title compound as a white solid (1.4 g). 1H NMR (CDCl3): 5 7.92-7.30 (m, 8H), 6.78 (s, 1H), 2.46 (s, 3H)

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; E. I. DU PONT DE NEMOURS AND COMPANY; WO2008/124092; (2008); A2;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

Application of 51572-93-1,Some common heterocyclic compound, 51572-93-1, name is O-(2,4-Dichlorobenzyl)hydroxylamine hydrochloride, molecular formula is C7H8Cl3NO, 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.

c) A solution of N-(2-butyryl-4-chlorophenyl)trifluoromethanesulfonamide 29A (243 mg, 0.74 mmol), O-(2,4-dichlorobenzyl)hydroxylamine hydrochloride (176 mg, 0.77 mmol) and anhydrous NaOAc (86 mg, 1.05 mmol) in EtOH (10 mL) was stirred for 15 hours at RT. The reaction mixture was concentrated under vacuum and the residue filtered through a pad of silica (eluting with CHCl3). Purification by radial thin layer chromatography (eluting with CH2Cl2/PE, 7.5:82.5 to 3:17) afforded N-{4-chloro-2-[1-(2-chloro-4-methylbenzyloxyimino)butyl]}trifluoromethanesulfonamide 100 (189 mg, 51%) as a pale yellow solid. M.p. 65-66 C. 1H n.m.r. (200 MHz, CDCl3) delta11.45, br s, 1H; 7.63, d, J=9.0 Hz, 1H; 7.46, d, J=2.6 Hz, 1H; 7.44, d, J=1.8 Hz, 1H; 7.41-7.34, m, 2H; 7.30-7.25, m, 1H; 5.27, s, 2H; 2.80, m, 2H; 1.60, m, 2H; 1.02, t, J=7.4 Hz, 3).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route O-(2,4-Dichlorobenzyl)hydroxylamine hydrochloride, its application will become more common.

Reference:
Patent; Meyer, Adam Gerhard; Winzenberg, Kevin Norman; Sawutz, David G.; Liepa, Andris Juris; US2006/63841; (2006); 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. 14862-52-3, name is 3,5-Dibromochlorobenzene, A new synthetic method of this compound is introduced below., SDS of cas: 14862-52-3

In the round bottom flask was charged with 1,3-dibromo-5-chlorobenzene 25g (92.47mmol) and biphenyl-4-yl-phenyl amine 45.4g (184.9mmol) into a sodium t- butoxide 26.7g (277.41mmol) was added to 463ml toluene dissolved. Here Pd (dba)2 0.266g (0.462mmol) and tri-tert-butylphosphine was put 0.187g (0.924mmol) in turn and the mixture was stirred under reflux for 4 hours under a nitrogen atmosphere. After the reaction the organic layer was then extracted with ethyl acetate dry distilled over magnesium sulfate, filtered and the filtrate was concentrated under reduced pressure. Silica gel with: a product n- hexane / dichloromethane (2 volume ratio of 8) The desired compound was purified by column chromatography of the intermediate M-12 to give the 44.9g (81% yield) as a white solid.

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; Chei Industries Inc.; Ryu, Dong Wan; Heo, Dal Ho; Jung, Seong Hyeon; Hong, Jin Seok; Kim, Jun Seok; Yoo, Dong Kyu; Lee, Seung Jae; Lee, Han Il; Chang, Yu Na; Cho, Yeong Kyeong; Chae, Mi Yeong; (44 pag.)KR2016/8651; (2016); A;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

Electric Literature of 210532-25-5, The chemical industry reduces the impact on the environment during synthesis 210532-25-5, name is 3,5-Difluorobenzene-1-sulfonyl chloride, I believe this compound will play a more active role in future production and life.

1.132 g (5.32 mmol) of 3,5-difluorobenzene-1-sulfonyle chloride is added under argon to a solution of 545 mg (3.55 mmol) of 5-amino-2-chloronicotinotrile in 20 mL of an anhydrous 1:1 mixture of THF and pyridine. The reaction medium is heated to 70C for 3 hours and let 12 additional hours under stirring at room temperature. The solvent is dry evaporated and the crude reaction product is redissolved in ethyl acetate and washed with several aqueous fractions. The organic phase is dried on magnesium sulfate, filtered, concentrated and then purified by silica gel chromatography to yield 784 mg (67%) of N-(6-chloro-5-cyanopyridin-3-yl)-3,5-difluorobenzene-sulfonamide. 1H NMR: deltaH ppm (400 MHz, DMSO) : 11,39 (1H, sl, NH), 8. 34 (1H, m, CHarom), 8,10 (1H, m, CHarom), 7,67 (1H, m, CHarom), 7,59 (2H, m, CHarom).

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, 3,5-Difluorobenzene-1-sulfonyl chloride, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; PIERRE FABRE MEDICAMENT; Kruczynski, Anna; Creancier, Laurent; Kaloun, El Bachir; Bedjeguelal, Karim; Rabot, Remi; EP2689779; (2014); A1;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

Synthetic Route of 1996-29-8, 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. 1996-29-8, name is 1-Bromo-4-chloro-2-fluorobenzene belongs to chlorides-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below.

Potassium /-butoxide (3.9 g, 0.33 mmol) was dissolved in DMSO (25 mL). To this solution was added 3 -methyl pyrazole (2.7 g, 0.33 mmol) and the reaction was heated at 50 C for 30 min. l-Bromo-4-chloro-2-fluorobenzene (4.6 g, 0.22 mmol) was then added and the reaction was stirred at 50 C for 16 h. The reaction was cooled to RT and extracted with water and EtOAc, washed with brine, and dried over Na2S04) filtered and concentrated in vacuo. Purification by normal phase silica gel column chromatography (EtO Ac/heptane) provided l-(2- bromo-5-chlorophenyl)-3-methyl-lH-pyrazole and l-(2-bromo-5-chloroplienyl)-5-methyl-lH- pyrazole as a 4: 1 mixture that was used in the next step directly,

The synthetic route of 1-Bromo-4-chloro-2-fluorobenzene has been constantly updated, and we look forward to future research findings.

Reference:
Patent; KAROS PHARMACEUTICALS, INC.; DE LOMBAERT, Stephane; GOLDBERG, Daniel R.; BRAMELD, Kenneth; SJOGREN, Eric Brian; SCRIBNER, Andrew; WO2015/35113; (2015); A1;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

Synthetic Route of 220227-21-4, 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. 220227-21-4 name is 2,4,5-Trifluorobenzene-1-sulfonyl chloride, 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.

To a solution of the N-(2,4-dimethoxybenzyl)pyri-midin-4-amine(0.76 g, 3.10 mmol) prepared in Example la and l,4-diazabicyclo[2.2.2]octane(0.70 g, 6.20 mmol) in acetonitrile (20 mL), 2,4,5-trifluorobenzenesulfonylchloride (1.43 g, 6.20 mmol) was added with cooling on ice, and thereaction solution was stirred at room temperature for 1 hour. The reactionsolution was filtered, the filtrate was concentrated under reduced pressure,and the residue was purified with silica gel chromatography (hexane/ethylacetate=67:33) to yield the title compound (0.72 g, 53%) as a colorless solid.

At the same time, in my other blogs, there are other synthetic methods of this type of compound, 2,4,5-Trifluorobenzene-1-sulfonyl chloride, and friends who are interested can also refer to it.

Reference:
Patent; Daichi Sankyo Corporation; Takahashi, Sakiko; Domon, Yuki; Kitano, Yutaka; Sinojika, Tsuyoshi; (102 pag.)KR2015/126620; (2015); A;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

Electric Literature of 13918-92-8,Some common heterocyclic compound, 13918-92-8, name is 2,4-Difluorobenzene-1-sulfonyl chloride, molecular formula is C6H3ClF2O2S, 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 flask containing 10 mmol of 3,4-methylenedioxyphenethylamine in 80 mL of dichloromethane was placed in an ice bath, then 13 mmol of pyridine was added to provide an alkaline environment. While stirring, 2 mmol of 2,4-difluorobenzenesulfonyl chloride was slowly added dropwise. After lh, the ice bath was removed, and the reaction was continued at room temperature for 3 h to stop the reaction. The reaction solution was washed with water three times, washed once with saturated sodium chloride and dried over anhydrous sodium sulfate. The solvent is recovered by filtration and rotary distillation, and hexane is added to the remaining oily liquid to crystallize. After the crystals are completely crystallized, the product is recrystallized to give the product as a pale yellow solid, N-(2,4-difluorobenzenesulfonyl)-3,4-methyleneoxyphenylethylamine, yield 99%.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 2,4-Difluorobenzene-1-sulfonyl chloride, its application will become more common.

Reference:
Patent; Hebei University of Science and Technology; Liu Shouxin; Zhang Xiaofang; Zhang Zhiwei; Yang Yihua; Yang Jianhua; (12 pag.)CN104045645; (2018); B;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

Reference of 1996-30-1, 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. 1996-30-1, name is 3-Bromo-4-fluorochlorobenzene belongs to chlorides-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below.

[00227] Step 12. 3-Bromo-5-chloro-2-fluorobenzaldehyde. A solution of 2,2,6,6- tetramethylpiperidine (327 g, 98%, 2.274 mol) and THF (1.9 L, HPLC grade) was cooled to -75 0C (dry ice-methanol bath) under an argon atmosphere. 1.6 M n-BuLi/hexane solution (1.47 L, 2.35 mol) was added slowly into the mixture at -72 to -67 0C over 1 h. The mixture was stirred at -72 to -67 0C for 30 min to give a pale yellow suspension. 2-Bromo-4-chloro-l-fluorobenzene (435 g, 97%, 2.02 mol) was added slowly into the mixture at -72 to -67 0C over 30 min, and then the mixture was stirred at -72 to -67 0C for an additional 30 min. Dimethylformamide (230 g, 99.5%, 3.14 mol) was added slowly into the mixture at -70 to -65 0C over 30 min and then the mixture was stirred at -70 to -65 0C for 30 min to afford a light brown solution. The cooling bath was removed and then saturated ammonium chloride solution (720 mL) was added into the batch at -60 to -30 0C over 15 min to obtain a hazy mixture. 6 N hydrochloric acid was quickly added into the mixture at -30 to 10 0C over 15 min to pH 1 and then ethyl acetate (2.0 L) was added at 10 to 20 0C. The layers were separated and the aqueous layer was extracted with ethyl acetate (1 x 300 mL). The combined organic extracts were washed with water (I x 800 mL) and brine (I x 500 mL), dried over magnesium sulfate, and filtered. The filtrate was concentrated under vacuum (60-65 0C) to give the title compound as a tan viscous oil, which solidified upon standing after several hours. 1H NMR (CDCl3): delta 7.76-8.30 (m, 2H), 10.0-10.8 (br s, IH); MS m/z 238.0 (M+l).

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

Reference:
Patent; IRM LLC; NOVARTIS AG; HUANG, Shenlin; JIN, Xianming; LIU, Zuosheng; POON, Daniel; TELLEW, John; WAN, Yongqin; WANG, Xing; XIE, Yongping; WO2011/25927; (2011); A1;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

Synthetic Route of 56131-46-5, 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. 56131-46-5 name is 3-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.

Reference Example 14 3-Bromo-2-chloro-N-cyclopropylaniline hydrochloride To a solution of 3-bromo-2-chloroaniline in methanol (25 ml)-acetic acid (5.4 ml), [(1-ethoxycyclopropyl)oxy]trimethylsilane was added dropwise at room temperature, and the mixture was stirred at 68¡ãC for 3 hr. The reaction mixture was allowed to cool to room temperature, and concentrated under reduced pressure (residue A). To a suspension of sodium borohydride (1.8 g) in THF(25 ml), boron trifluoride diethyl ether complex (6.0 ml) was added dropwise under nitrogen atmosphere at 0¡ãC, and the mixture was further stirred for 1 hr. A solution of residue A in THF (15 ml) was added dropwise to the mixture at 0¡ãC, and the mixture was stirred at room temperature for 3 hr, and at 60¡ãC overnight. Water was added to the reaction mixture at 0¡ãC, and the mixture was extracted with ethyl acetate. The organic layer was washed with saturated brine, and dried over anhydrous magnesium sulfate. The solvent was evaporated under reduced pressure. The obtained residue was purified by silica gel column chromatography. 4N Hydrogen chloride-ethyl acetate (60 ml) was added, and the mixture was stirred for 10 min. The solvent was evaporated under reduced pressure, and the obtained residue was washed with ethyl acetate to give the object (3.46 g) as crystals. 1H-NMR (DMSO-d6) delta0.47-0.54 (2H, m), 0.70-0.78 (2H, m), 2.35-2.44 (1H, m), 6.26 (2H, br s), 6.97 (1H, dd), 7.03 (1H, dd), 7.11 (1H, t).

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

Reference:
Patent; Takeda Pharmaceutical Company Limited; EP1847541; (2007); A1;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

Related Products of 97329-43-6, 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 97329-43-6 as follows.

To a stirred solution of 3-bromo-6-chloropyrazin-2-amine (0.3 g, 1.43 mmol) in THF:H2O (20 ml, 9:1), and mixture of boronic acid and ester (0.3 g, crude), sodium carbonate (0.46 g, 4.31 mmol) were added. The reaction mixture was degassed with argon for a 10 minutes and Pd(PPh3)4 (0.16 g, 0.14 mmol) was added. The reaction mixture was degassed again with argon and heated at 80 C. with stirring for 12 h. Progress of the reaction was monitored by TLC, which showed complete consumption of starting material. The reaction mixture was allowed to cool to room temperature and concentrated. The residue was diluted with water (20 mL) and the extracted with EtOAc (3*20 mL). The combined organic layer was washed with brine (40 mL), dried over Na2SO4, filtered, and concentrated. The residue was purified by column chromatography [silica gel (100-200 mesh), gradient 4% to 6% ethyl acetate in hexane] to give 6-chloro-3-(2-chloro-3-methylphenyl)pyrazin-2-amine (0.28 g, 76%) as a yellow solid. MS (ESI+ve): 253.92 1H-NMR (400 MHz; DMSO-d6): delta 7.82 (s, 1H), 7.44-7.46 (d, J=7.20 Hz, 1H), 7.32-7.36 (t, J=7.6 Hz, 1H), 7.20-7.22 (d, J=6.8 Hz, 1H), 6.51 (bs, 2H), 2.40 (s, 3H).

According to the analysis of related databases, 97329-43-6, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Krouzon Pharmaceuticals, Inc.; Volkmann, Robert; Marfat, Anthony; Nelson, Frederick; Zagouras, Panayiotis; (44 pag.)US2019/77792; (2019); A1;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics