Month: November 2020

60811-21-4, These common heterocyclic compound, 60811-21-4, name is 4-Bromo-2-chloro-1-fluorobenzene, 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.

Compound 10H- spiro [fluorene-9,9′ acridine] (16.55g, 50mmol)And 4-bromo-2-chloro-1-fluorobenzene (10.50g, 50mmol)Add in a three-necked flask,Stir and dissolve with 200 mL of N,N-dimethylformamide (DMF).Nitrogen protection,Then add Cs2CO3 (19.5g, 60mmol)And K2CO3.The reaction solution was stirred and refluxed for 12 hours.After cooling, the reaction solution was poured into 1000 mL of water, and 2 filtered, and the filter cake was washed with a mixed solvent of ethanol and petroleum ether, and suction filtered.The filter cake was recrystallized from a mixed solvent of dichloromethane and petroleum ether (DCM/PE).The compound 1-1 (16.09 g, yield 62%) was obtained as a white solid.

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 60811-21-4.

Reference:
Patent; Guangzhou Huarui Optoelectric Materials Co., Ltd.; Yang Xi; Pan Junyou; Wang Pu; (50 pag.)CN109651369; (2019); A;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

108-37-2, A common compound: 108-37-2, name is 1-Bromo-3-chlorobenzene, 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.

General procedure: To a round-bottom flask equipped with a magnetic stirring bar were added monomeric palladacycle 2 (0.4 mol %), K2CO3 (1.1 mmol), olefin (2.2 mmol) and aryl halide (1 mmol) in NMP (3 mL). The mixture was heated at 130 C using an oil bath and the progress was monitored by TLC (hexane/EtOAc, 80:20) and gas chromatography (GC). After completing the reaction, the mixture was diluted with n-hexane (30 mL) and H2O. The organic layer was washed with brine (20 mL), dried over Na2SO4, and concentrated under reduced pressure. The residue was purified by recrystallization from EtOH and H2O. The products were characterized by comparing their mp and IR, 1H and 13C NMR spectra with those reported in the literature.

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-Bromo-3-chlorobenzene, other downstream synthetic routes, hurry up and to see.

Reference:
Article; Hajipour, Abdol Reza; Rafiee, Fatemeh; Rouho, Arnold E.; Tetrahedron Letters; vol. 52; 37; (2011); p. 4782 – 4787;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

41965-95-1, A common compound: 41965-95-1, name is 3-Chloro-4-methoxybenzylamine Hydrochloride, 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.

A mixture of 4 (0.12 mmol), 3~ehoro-4-methoxyhenzylamine hydrochloride (0.12 mmol), Nal (0.006 mmol), and phenol (0.12 mmol) was heated at 130 “C for 2.5 h. The reaction mixture was diluted with Et20 ( 10 mL) and washed with IN NaOH (3×5 mL). The organic layer was dried over Na2S0 , filtered and evaporated under reduced pressure. The residue was purified by Flash Chromatography (AcOEt: MeOH 8:2) to give the desired compound B (33% of yield). MS ESI (m/z) 394 (M+ j ), H NMR (300 MHz, CDCI3) delta 8.32 (d, 1 H, J= 1.2 Hz), 7.97 (d, 1H, J= 8.7 Hz), 7.71 (dd, 1H, J,= 1 .8, J2= 8.7 Hz), 7.37 (d, 1H, J= 2.1 Hz), 7.18 (dd, 1H, Jx= 2.4, J2= 8.7 Hz), 6.94 (d, 1H, J- 8.4 Hz), 4.57 (d, 2H, J= 6.0 Hz), 4.1 1 (br s, 1H), 3.92 (s, 3H), 3.54 (s, 2H), 3.22 (t, 2H, J= 6.3 Hz), 2.83 (t, 2H, J= 6.3 Hz), 2.52 (s, 3H).

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-Chloro-4-methoxybenzylamine Hydrochloride, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; THE TRUSTEES OF COLUMBIA UNIVERSITY IN THE CITY OF NEW YORK; LANDRY, Donald, W.; DENG, Shixian; ARANCIO, Ottavio; FIORITO, Joie; WASMUTH, Andrew; WO2013/109738; (2013); A1;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

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. 39989-43-0 name is 3,5-Dichlorobenzylamine, 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. 39989-43-0

To a solution of 3,5-dichlorobenzylamine (12 mg, 0.068 mmol) in DCM (0.2 mL) was added a solution of 9 (13 mg, 0.054 mmol) in DCM (0.5 mL) at room temperature. The resulting mixture was stirred until all of the 9 had been consumed (within one hr) and then was used straight in the next reaction. MS (ESI) 415 (M+1); HPLC tR 6.00 min.

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

Reference:
Patent; MIMETICA PTY LTD; US2012/141392; (2012); A1;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

81927-55-1, These common heterocyclic compound, 81927-55-1, name is Benzyl 2,2,2-trichloroacetimidate, 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.

A stirred solution of (R)- methyl 3-hydroxy-2-methylpropanoate (9.57 g, 81.0 mmol) and benzyl 2,2,2- trichloroacetimidate (22.50 g, 89.1 mmol) in CH2Cl2 (10 mL) was cooled to 0 0C under N2. Triflic acid (0.1 mL) in CH2Cl2 (1 mL) was added dropwise. After 10 minutes the reaction became a solid mass. After 1 hour, saturated aqueous NaHCO3 was added and the mixture extracted with Et2O. The organics were dried over MgSO4, filtered and concentrated on a rotary evaporator. Hexane was added and the resulting solids collected by vacuum filtration. The filtrate was concentrated on a rotary evaporator and purified using flash chromatography (5-10% EtOAc/hexane) to give 10.39 g (62%) of (R)-methyl 3-(benzyloxy)-2- methylpropanoate as a colorless oil. Rf= 0.20 (10% EtOAc/hexane). 1H NMR (300 MHz, DMSO-D6) delta ppm 1.08 (d, J=7.14 Hz, 3 H) 2.75 (ddd, J=14.01, 12.64, 7.14 Hz, 1 H) 3.44 – 3.59 (m, 2 H) 3.60 (s, 3 H) 4.46 (s, 2 H) 7.23 – 7.40 (m, 5 H).

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 81927-55-1.

Reference:
Patent; SIGNAL PHARMACEUTICALS, LLC; WO2007/84560; (2007); A2;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

13526-66-4, 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. 13526-66-4, name is 3-Bromo-6-chloroimidazo[1,2-b]pyridazine, This compound has unique chemical properties. The synthetic route is as follows.

a) S-Bromo-e-il-methyl-piperidin^-yloxyJ-imidazotl^-i lpyridazine To a suspension of NaH (60% in oil, 0.17 g, 4.31 mmol) in dry THF (5 mL) at 0 C was added a solution of 4-hydroxy-/V-methyl piperidine (0.50 g, 4.31 mmol) in dry THF (5 mL). The reaction mixture was stirred a 0C for 5 min then at RT for 15 min. The reaction mixture was cooled back to 0C and a solution of 3-bromo-6-chloroimidazo[1 ,2- ?>]pyridazine (0.50 g, 2.15 mmol) in dry THF (10 mL) was added dropwise. The reaction mixture was then allowed to warm up slowly to RT and stirred for 4 h. The reaction mixture was quenched by addition of water (10 mL), diluted with EtOAc (100 mL) and washed with water (2 x 50 mL). The organic layer was dried and concentrated in vacuo. Purification by column chromatography (EtOAc-2M NH3 in MeOH 5-100%) gave a solid (0.35 g, 53%); 1H NMR (400 MHz, DMSO-d6) delta ppm 8.04 (d, J=9.6 Hz, 1 H), 7.73 (s, 1H), 6.93 (d, J=9.6 Hz, 1 H), 4.99 (m, 1 H), 2.75-2.56 (m, 2H), 2.27-2.13 (m, 5H), 2.13-2.01 (m, 2H), 1.90-1.65 (m, 2H); m/z (ES+APCI)+: 311/313 [M+H]+.

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; MEDICAL RESEARCH COUNCIL TECHNOLOGY; OSBORNE, Simon; CHAPMAN, Timothy; LARGE, Jonathan; BOULOC, Nathalie; WALLACE, Claire; WO2011/101640; (2011); 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. 1996-30-1, name is 3-Bromo-4-fluorochlorobenzene, A new synthetic method of this compound is introduced below., 1996-30-1

A mixture of 2-30 (1.04 g, 5 mmol), (PinB)2 (2.28 g, 9 mmol), Pd(dppf)C12DCM (408 mg, 0.5 mmol), KOAc (980 mg, 10 mmol) and dioxane (5 mL) was degassed with N2 and stirred at 95 C overnight. The resulting mixture was filtered and the filtrate was concentrated and purified by column chromatography on silica gel eluting with PE/ethyl acetate from 20/1 to 10/1 to provide intermediate 2-31 (806 mg, 63% yield) as a yellow solid. LCMS (m/z): 173 [M-H-82j -.

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; DANA-FARBER CANCER INSTITUTE, INC.; FONDAZIONE CENTRO SAN RAFFAELE; GRAY, Nathanael S.; BUHRLAGE, Sara; ANDERSON, Kenneth; COTTINI, Francesca; TONON, Giovanni; (288 pag.)WO2016/161145; (2016); A1;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

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