Chlorides-buliding-blocks

These common heterocyclic compound, 108-70-3, name is 1,3,5-Trichlorobenzene, 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. 108-70-3

General procedure: An oven-dried and argon-flushed pressure tube was charged with 1,3,5-trichlorobenzene, 1,2,4-trichlorobenzene or 1,2,3-trichlorobenzene (0.25 mmol), Pd2(dba)2 (1.25 mol%), cataCXium A (5.0 mol%), boronic acid (1.5 mmol) and K3PO4 (1.5 mmol) followed by anhydrous toluene (4.0 mL). The tube was sealed with a Teflon valve and the reaction mixture was stirred at 110 C for 24 h. The cooled reaction mixture was diluted with water and extracted with DCM. The combined organic layers were dried (Na2SO4), filtered and the filtrate was concentrated in vacuo. The residue was purified by column chromatography.

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 108-70-3.

Reference:
Article; Reimann, Sebastian; Ehlers, Peter; Sharif, Muhammad; Spannenberg, Anke; Langer, Peter; Tetrahedron; vol. 72; 8; (2016); p. 1083 – 1094;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

112-26-5, 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. 112-26-5 name is 1,2-Bis(2-chloroethoxy)ethane, 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.

It includes the following steps: 1. Feeding To a 2L four-necked flask equipped with a stirrer, a thermometer, and a condenser, which is protected by nitrogen, add 225.3g of triethylene glycol (content 99.6%, 1.5mol), 750g of tetrahydrofuran, and 322g of homemade dichlorotriethylene glycol (content 95.82%) , 1.65mol), stir well and mix evenly. 2. Add potassium hydroxide The temperature was raised with an electric heating mantle, and the reflux started when the temperature reached 70C. 240g (3.96mol) of potassium hydroxide was added to the reaction solution in 12 portions, once every 1h, for a total of 12 additions. The potassium hydroxide is industrial grade with a purity of more than 90%. 3. Insulation reaction After the addition of potassium hydroxide is completed, continue to reflux for 1h. When the gas phase detection of dichlorotriethylene glycol content is less than 0.5%, the reaction can be considered as completed.If the dichlorotriethylene glycol content does not decrease during the gas phase tracking process, it is necessary to continue to add potassium hydroxide until the dichlorotriethylene glycol is consumed. 4. Distilled tetrahydrofuran and water After the heat preservation reaction is completed, the reaction liquid is cooled to below 50C, and the device is changed to a distillation device.Tetrahydrofuran is recovered by atmospheric distillation, and the temperature of the kettle is controlled at 100 at the end of one distillation. Distilled about 750g of tetrahydrofuran and water mixture, with about 3.5% water; Control the pressure of the distillation system to -0.03mpa, and raise the temperature to 100 for 0.5h, Stop the distillation and distill off about 13g of distillate; after the distillation is completed, lower the kettle temperature to below 40. 5. Add dichloromethane Add 600g of methylene chloride to the kettle liquid after distillation and continue to stir at low temperature for 10min; Filter with a Buchner funnel. After the first filtration, wash the filter cake with 300 g of methylene chloride.After washing and filtering, the potassium chloride is slightly yellow, and the salt mass is about 308g. 6. Distilled methylene chloride and water The washing liquid and the filtrate are mixed into a 2000ml four-necked flask. After stirring, 80% sulfuric acid is added dropwise, the system pH is adjusted to 7, and the acid amount is about 4-6g; Build a distillation device, transfer the neutral materials, distill methylene chloride at atmospheric pressure, stop the atmospheric distillation when the temperature of the distillation kettle is about 120C, weigh the distillate and collect it. At this time, the temperature of the system was 120C, the pressure was adjusted to -0.01mpa, and the remaining liquid was distilled under reduced pressure. At this time, the distillate is mainly water, and the vacuum is gradually increased until the pressure is -0.08mpa.The distillate does not flow out, and the temperature is raised to 130C for 0.5h and then cooled, and the distillation is stopped.Among them, about 750 g of distillate was distilled under normal pressure, and 31 g of distillate was distilled under reduced pressure. 7. Distilled crown ether Reduce the temperature of the material to below 60C, transfer to a 1L high vacuum distillation unit, and gradually pump the vacuum to a maximum of about 40pa with an Edward vacuum pump. When the kettle temperature is 150, the distillate begins to flow out. At 180-210C, the distillate flows out faster. The top temperature is stable at 168-172C. When the kettle temperature rises to 230C, the fraction hardly comes out, the top temperature starts to drop, and the distillation ends.Cool down, stop the vacuum pump after the material cools to below 100, and vent the system with nitrogen; 8. Purification of crude products (1) Add acetonitrile Weigh 250g of acetonitrile and transfer to a 1000ml four-necked flask. (2) Add crude crown ether dropwise Under the stirring state, 170g of the above distillate was added with a constant pressure dropping funnel, the dropping process was exothermic, the dropping was completed in about 0.5h, and a lot of turbidity appeared during the dropping process. (3) Heating up After the addition is completed, the temperature is increased by heating, and the temperature of the feed becomes clear after rising to 58C. (4) Cooling and crystallization Then the temperature was lowered. When the temperature dropped to 56, the feed liquid became cloudy. When the temperature continued to drop naturally to 40, the solution was placed in a cold bath at -10 (the temperature gradually decreased to -10) and the crystallization speed was 100 rpm. Stirring is stopped every 1h during the crystallization process, and after standing, the supernatant liquid is taken to detect the content of crown ether in the gas phase.Until the crown ether content no longer decreases to 0.3% stop stirring, about 4h, ready to filter. (5) Filtration and washing Filter with a Buchn…

At the same time, in my other blogs, there are other synthetic methods of this type of compound, 1,2-Bis(2-chloroethoxy)ethane, and friends who are interested can also refer to it.

Reference:
Patent; Weifang Binhai Petrochemical Co., Ltd.; Zhang Junying; Chen Zhidong; Dou Rongtan; Sun Congming; Yang Wentao; Hao Jiuxiang; Zhou Chengwei; (7 pag.)CN111087382; (2020); A;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

874-17-9, Adding some certain compound to certain chemical reactions, such as: 874-17-9, name is 4-Chloro-2,6-dibromoaniline, 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 874-17-9.

Under a nitrogen stream, 2,6-dibromo-4-chloroaniline (20.0 g, 70.08 mmol),Pd (PPh3) 4 (4.04 g, 3.50 mmol) was added to the reaction solution after stirring the mixture with phenylboronic acid (8.54 g, 83.01 mmol), K2CO3 (29.05 g, 210.24 mmol) and Toluene / H2O / EtOH Mmol) were added thereto, and the mixture was stirred at 100 C for 5 hours. After completion of the reaction, the reaction mixture was extracted with methylene chloride, concentrated under reduced pressure, and subjected to column chromatography to obtain the objective compound 4-chloro-2,6-diphenylaniline (15.8 g).

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 874-17-9.

Reference:
Patent; Doosan Corporation; Son, Hyo Suk; Sim, Jae Uii; Lee, Jae Hun; Park, Ho Chul; Lee, Chang Jun; Sin, Jin Yong; Baek, Young Mi; (46 pag.)KR2015/87045; (2015); A;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

A common heterocyclic compound, 104-52-9, name is 3-Phenylpropyl Chloride, molecular formula is C9H11Cl, 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. 104-52-9.

To a suspended solution of AlCl3 (8.69 g, 65.2 mmol) and 3-chloropropionylchloride(9.97 g, 64.5 mmol) in dichloromethane (70 mL) was added 3-phenylpropylchloride(7.91 g, 62.8 mmol). The mixture was stirred at room temperature for 4 h and thenquenched by saturated NaHCO3 aq (100 mL). The mixture was extracted with diethylether (100 x 3 mL). The collected organic layer was washed with water (100 x 2 mL)and saturated NaCl aq (100 mL) and then dried (MgSO4). The solvent was evaporatedand the residue was washed with hexane to give the product as white solid (9.73 g,63%).

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

Reference:
Article; Nishimoto, Yoshihiro; Yazawa, Satoshi; Kiyokawa, Kensuke; Kajiki, Takahito; Tsukahara, Yasunori; Yamauchi, Tomohisa; Wada, Yuji; Baba, Akio; Yasuda, Makoto; Chemistry Letters; vol. 46; 8; (2017); p. 1116 – 1118;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

Adding some certain compound to certain chemical reactions, such as: 202197-26-0, name is 3-Chloro-4-((3-fluorobenzyl)oxy)aniline, 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 202197-26-0. 202197-26-0

Example 17 O-{4-[-3-chloro-4-(3-fluorobenzyloxy)-phenylamino]-quinazolin-6-yl}-acetate 6-acetoxy-4-chloroquinazoline (0.90 g, 4.04 mmol) and 3-chloro-4-(m-fluoro-benzyloxy)-aniline (1.00 g, 3.97 mmol) were dissolved into 40 mL of isopropanol, and the mixture was stirred under reflux for 3 h. A lot of light grey solid was deposited, which was filtered, and the filter cake was washed with small quantity of ethyl acetate and dried under vacuum at 60 C. overnight to obtain the title compound (1.65 g, 95%). 1H-NMR (400 MHz, CDCl3): delta8.68(1H, s), 7.89-7.81 (2H, m), 7.58-7.48 (2H, m), 7.40-7.32 (1H, m), 7.27-7.19 (3H, m), 7.16 (1H, d, J=2.46 Hz), 7.07-6.96 (2H, m), 5.14 (2H, s), 2.11 (3H, s).

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 3-Chloro-4-((3-fluorobenzyl)oxy)aniline.

Reference:
Patent; SHANGHAI ALLIST PHARMACEUTICALS, INC.; US2008/300248; (2008); A1;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

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.

This experiment was carried out in two batches of the same scale. n-Butyllithium (2.5 M solution in hexanes; 32.8 mL, 82.0 mmol) was slowly added to a -70 C. solution of 1-bromo-4-chloro-2-fluorobenzene (17.2 g, 82.1 mmol) in diethyl ether (100 mL), while the temperature of the reaction mixture was maintained below -60 C. After the reaction mixture had been stirred at -70 C. for 20 minutes, a solution of 3-bromo-2-hydroxybenzaldehyde (5.5 g, 27 mmol) in diethyl ether (100 mL) was slowly added, while the reaction temperature was maintained below -60 C. After a further 1 hour of stirring at -70 C., the reaction was quenched by addition of aqueous ammonium chloride solution (50 mL) at -70 C., and the resulting mixture was diluted with water (100 mL). The two batches were combined at this point and extracted with ethyl acetate (400 mL); the organic layer was washed with saturated aqueous sodium chloride solution (200 mL), dried over sodium sulfate, filtered, and concentrated in vacuo. Silica gel chromatography (Gradient: 0% to 7% ethyl acetate in petroleum ether) afforded C1 as a white solid. Combined yield: 15.7 g, 47.4 mmol, 88%. 1H NMR (400 MHz, chloroform-d) delta 7.44 (dd, J=8.0, 1.5 Hz, 1H), 7.37 (dd, J=8.1, 8.1 Hz, 1H), 7.15 (br dd, J=8.5, 2.1 Hz, 1H), 7.12-7.05 (m, 2H), 6.80 (dd, J=7.8, 7.8 Hz, 1H), 6.78 (s, 1H), 6.31 (d, J=4.8 Hz, 1H), 3.02 (brd, J=4.9 Hz, 1H).

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

Reference:
Patent; Pfizer Inc.; Aspnes, Gary Erik; Bagley, Scott W.; Curto, John M.; Edmonds, David James; Flanagan, Mark E.; Futatsugi, Kentaro; Griffith, David A.; Huard, Kim; Lian, Yajing; Limberakis, Chris; Londregan, Allyn T.; Mathiowetz, Alan M.; Piotrowski, David W.; Ruggeri, Roger B.; (127 pag.)US2019/382384; (2019); A1;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

108-70-3, name is 1,3,5-Trichlorobenzene, 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. 108-70-3

To a 250 ml single-necked flask was placed 9.5 g (52.4 mmol) of 1,3,5-trichlorobenzene and 100 ml of ultra-dry tetrahydrofuran under argon protection and minus 78 degrees Celsius. Then, 26.3 ml (2 Torr, 52.6 mmol) of lithium diisopropylamide in tetrahydrofuran/n-hexane solution was added dropwise, and the mixture was stirred at minus 78 C for 30 minutes. Then, 10.0 g (47.7 mmol) of Compound A1 was added, and stirring was continued for 2 hours at minus 78 C. The reaction was then slowly warmed to room temperature and quenched by the addition of 200 mL of saturated aqueous ammonium chloride. The combined organic layers were washed with brine (25 mL) After evaporating the solvent, it was purified by column chromatography using methylene chloride: petroleum ether: 1:1 (volume ratio) as eluent to afford 17.5 g of product A2, yield 94%.

Statistics shows that 108-70-3 is playing an increasingly important role. we look forward to future research findings about 1,3,5-Trichlorobenzene.

Reference:
Patent; Jilin University; Li Feng; Ai Xin; Zhang Ming; (25 pag.)CN108191739; (2018); A;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

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. 108-41-8, name is 1-Chloro-3-methylbenzene belongs to chlorides-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below. 108-41-8

Example 6: 3-Chlorobenzoic Acid In a 100 ml jacketed vessel, 200 ml of acetic acid, 0.08 g of cerium(III) acetate, 4.9 g of sulfuric acid and 12.65 g of 3-chlorotoluene were initially charged. The mixture was cooled to 16 C. and 5.15 g of ozone were introduced within a period of 75 minutes. After completion of ozonolysis, the ozone present in the solvent was blown out using nitrogen. Analysis of the reaction mixture by means of HPLC or GC gave the following results: 3-chlorotoluene: >0.1%; 3-chlorobenzoic acid: 98%

The synthetic route of 108-41-8 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Jary, Walther; Poechlauer, Peter; Ganglberger, Thorsten; US2003/216577; (2003); A1;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

3386-33-2, Adding a certain compound to certain chemical reactions, such as: 3386-33-2, name is 1-Chlorooctadecane, 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 3386-33-2.

Diallylphenol (3.48 gm, 0.02 mol) was diluted in dimethyl sulfoxide (50 ml) and sodium hydroxide (0.8 gm, 0.02 mol) added to the solution followed by 1-chlorooctadecane (5.78 gm, 0.02 mol) and heated at 80 C. for 2 hrs. After cooling and diluting with water, the reaction mixture was extracted with hexane, dried over MgSO4 filtered and evaporated to give the desired product. MS m/z 426. (M+ calcd for C30H50O=426). H NMR (300 MHz, CDCl3) d 0.80 (t ,3, CH3), 1.25 (s, 32, CH2).1.75-1.80 (m, 2, CH2), 3.30-3.40 (d, 4, CH2), 3.70-3.80 (t, 2, OCH2), 5.05-5.21(m, 2, CH2 vinyl), 5.95-6.10 (m, 2,CH2 vinyl), 7.00-7.20(m, 3, aromatic). Oxidation with MCPBA as described in Example 1 gave 2,6-di(epoxypropyl)phenyl octadecyl ether. MS m/z 458 (M+ calcd for C30H50O3=458). H NMR (300 MHz, CDCl3) d 0.80 (t, 3, CH3), 1.25 (s, 30, CH2), 2.60-2.70 (m, 2, CH2 epoxypropyl), 2.75-3.10 (m, 6, CH2 epoxypropyl), 3.20-3.30 (m, 2, epoxypropyl CH), 3.55-3.75 (t, 2, CH2), 7.10-7.25 (m, 1, aromatic), 7.40-7.60 (m, 2, aromatic).

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-Chlorooctadecane, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; Pews, R. Garth; US2005/90673; (2005); A1;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

2533-69-9, A common compound: 2533-69-9, name is Methyl 2,2,2-trichloroacetimidate, belongs to chlorides-buliding-blocks compound, it can change the direction of chemical reaction, and react with certain compounds to generate new functional products. A new synthetic method of this compound is introduced below.

Reference Example 1 To 100 ml of acetic acid solution containing 20 g of 2-benzylamino-4-chloroaniline was added 15 ml of O-methyl-trichloroacetoimidate at 0 to 25 C., and stirred the mixture at room temperature for 3 hours. Then water was added to the reaction mixture, the separated crystals were collected by filtration to obtain 29.6 g of 1-benzyl-6-chloro-2-trichloromethylbenzimidazole in the form of pale brown powder. 1 H-NMR (250 MHz, DMSO-d6) delta ppm: 5.94 (2H, s), 7.04 (2H, d, J=6.5 Hz), 7.25-7.5 (5H, m), 7.88 (1H, d, J=9.0 Hz).

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, Methyl 2,2,2-trichloroacetimidate, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; Otsuka Pharmaceutical Co., Ltd.; US5998437; (1999); A;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics