Month: February 2021

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. 19752-55-7, name is 1-Bromo-3,5-dichlorobenzene belongs to chlorides-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below. Quality Control of 1-Bromo-3,5-dichlorobenzene

In the round bottom flask was charged with 1,3-dibromo-5-chlorobenzene 25g (92.47mmol) and phenoxazine 16.9g (92.47mmol) into a sodium t- butoxide 13.4g (138.7mmol) 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. The product n- hexane / dichloromethane (8: 2 by volume) to yield the silica gel column 25.7g (yield 85percent) of intermediate M-16 chromatography to yield the desired compound as a white solid.

The synthetic route of 19752-55-7 has been constantly updated, and we look forward to future research findings.

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

Reference of 4584-46-7, These common heterocyclic compound, 4584-46-7, name is 2-Chloro-N,N-dimethylethanamine hydrochloride, 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.

Intermediate 115yV,yV-Dimethyl-2-[4-(4,4,5,5-tetramethyl-1 ,3,2-dioxaborolan-2-yl)-1 H-pyrazol-1 – yljethanamine4-(4,4,5,5-Tetramethyl-1 ,3,2-dioxaborolan-2-yl)-1 /-/-pyrazole (2 g, 10.31 mmol), cesium carbonate (6.72 g, 20.61 mmol) and 2-chloro-/V,/V-dimethylethanamine hydrochloride (2.227 g, 15.46 mmol) were suspended in acetonitrile (30 mL) and the mixture was heated at reflux for 5 h, then cooled to room temperature, diluted with Et20 and filtered. The filtrate was concentrated in vacuo to give N,N-dimethyl-2-[4-(4,4,5,5-tetramethyl-1 ,3,2- dioxaborolan-2-yl)-1 H-pyrazol-1 -yl]ethanamine dimethyl{2-[4-(4,4,5,5-tetramethyl-1 ,3,2- dioxaborolan-2-yl)-1 H-pyrazol-1 -yl]ethyl}amine (2.61 g, 9.84 mmol, 95 % yield) as an amber oil which was used in the next step without further purification.

Statistics shows that 2-Chloro-N,N-dimethylethanamine hydrochloride is playing an increasingly important role. we look forward to future research findings about 4584-46-7.

Reference:
Patent; GLAXOSMITHKLINE LLC; DEMONT, Emmanuel, Hubert; GARTON, Neil, Stuart; GOSMINI, Romain, Luc, Marie; HAYHOW, Thomas, George, Christopher; SEAL, Jonathan; WILSON, David, Matthew; WOODROW, Michael, David; WO2011/54841; (2011); A1;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

Reference of 39226-96-5,Some common heterocyclic compound, 39226-96-5, name is (2-Chloro-3-(trifluoromethyl)phenyl)methanamine, molecular formula is C8H7ClF3N, 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 2,5-dimethyl-1 ,2,5-thiadiazolidine-3-carboxylic acid 1 ,1 -dioxide (136 mg, 0.700 mmol, prepared as described below), N-ethyl morpholine (0.268 ml, 2.100 mmol), 1-hydroxybenzotriazole hydrate (129 mg, 0.84 mmol) and 1 -ethyl-3-(3- dimethylaminopropyl)carbodiimide hydrochloride (161 mg, 0.840 mmol) in dichloromethane (9 ml) was stirred at room temperature for 10 minutes. A solution of {[2-chloro-3-(trifluoromethyl)phenyl]methyl}amine (147 mg, 0.700 mmol) in dichloromethane (1 ml) was added and the reaction stirred at room temperature for 3 hours. The reaction mixture was diluted with dichloromethane (10 ml) and the solution was washed with saturated sodium hydrogen carbonate solution (10 ml), water (10 ml), citric acid solution (10 ml) and brine (10 ml), dried and evaporated. The residue was purified by mass-directed automated HPLC. The residue was triturated with ether/isohexane and the solvent was evaporated. The residue was dried under high vacuum at room temperature using phosphorus pentoxide as drying agent to give N-{[2-chloro-3-(trifluoromethyl)phenyl]methyl}-2,5-dimethyl-1 ,2,5- thiadiazolidine-3-carboxamide 1 ,1 -dioxide (120 mg, 44%).LC/MS [M+H]+ = 386, retention time = 2.66 minutes.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route (2-Chloro-3-(trifluoromethyl)phenyl)methanamine, its application will become more common.

Reference:
Patent; GLAXO GROUP LIMITED; DEAN, David, Kenneth; WALTER, Daryl, Simon; WO2011/54947; (2011); A1;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

Reference of 53145-38-3, These common heterocyclic compound, 53145-38-3, name is 2-Chloro-6-fluoroanisole, 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.

5. Preparation of 4-chloro-2-fluoro-3-methoxybenzaldehyde To a solution of 2-chloro-6-fluoroanisole (321.2 g) in 2 L of dry tetrahydrofuran (THF), cooled to -70 C., was added 890 mL of 2.5 M n-BuLi in hexane over 30 min with good mechanical stirring. During the addition the reaction warmed to -48 to -50 C. and was held there for 15 min after addition was complete. The solution was cooled to -75 C. before a solution of 177 g of dimethylformamide (DMF) in 100 mL of THF was added keeping the temperature below -50 C. The reaction was warmed to room temperature and 260 g of 37% aqueous HCl was slowly added and stirring was continued for 2 hours. The phases were separated and the organic phase concentrated and taken into 2 L of ether. The solution was washed twice with 500 mL of aqueous 10% HCl. The organic phase was dried over MgSO4, filtered and concentrated to 372 g of a light gold oil (93% pure by GC). This oil was distilled bulb to bulb to give 282 g (75% yield) of a light gold oil that solidified upon standing. A small sample was crystallized from pentane to give fine white needles; MP 44-45 C.; 1H NMR (CDCl3, 300 MHz) delta 10.3 (s, 1H); 7.5 (dd, 1H, J=6.6, 8.5 Hz); 7.3 (m, 1H); 4.0 (s, 3H).

Statistics shows that 2-Chloro-6-fluoroanisole is playing an increasingly important role. we look forward to future research findings about 53145-38-3.

Reference:
Patent; Dow AgroSciences LLC; US2009/182168; (2009); A1;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

Application of 20850-43-5, 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 20850-43-5 as follows.

Preparation of 1, 3-benzodioxol-5-ylmetlyl ethyl sulfone 8.6 g of 5-(chloromethyl)-1, 3-benzodioxol was dissolved in 20 ml of anhydrous tetrahydrofuran and 20 ml of diethyl ether and then added to magnesium at 0C. The reaction was done for 10 minutes and then for 1 hour at 50C. The reaction mixture was cooled to 0C and then slowly added to the flask containing [1,3-bis (diphenylphosphino) propane] nickel (II) dichloride as a catalyst. After the addition of 3.7 ml ethane sulfonyl chloride, the mixture was reacted for 30 minutes. The reactant was then heated to 50C and reacted for 1 hour. Then, its pH was adjusted to 7 with dilute hydrochloric acid. The resulting mixture was extracted with diethyl ether and distilled water, dried over anhydrous magnesium sulfate and the solvent was removed. The residue was fractionated by column chromatography using ethyl acetate: n-hexane (1: 3), to give 0.3 g of the title compound of the following formula lb (Rf: 0.35, Yield: 3%). [Chemical Formula 1b] The compound was dissolved in CDC13 and TMS and then characterized by’H NMR spectroscopy. The result is as follows; ‘H NMR 5 : 1.57-1. 64 (t, 3H, J=7.3Hz), 2.78 (s, 2H), 3.60-3. 78 (q, 2H, J=7.3Hz), 5.90 (s, 2H), 6.56-6. 79 (m, 3H).

According to the analysis of related databases, 20850-43-5, the application of this compound in the production field has become more and more popular.

Reference:
Patent; HAN, Sang Min; LEE, Myung Hee; CHOI, Won Chul; WO2005/70915; (2005); A1;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

Adding a certain compound to certain chemical reactions, such as: 103889-37-8, name is 1-Chloro-3-fluoro-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 103889-37-8, Recommanded Product: 1-Chloro-3-fluoro-2-(trifluoromethyl)benzene

To a solution of conc. H2S04 (3 mL) and conc. HNO3 (3 mL) was added 1-chloro- 3-fluoro-2-(trifluoromethyl)benzene (1.00 g, 5.05 mmol) at 0C. The reaction mixture was stirred at 0C for 30 minutes and at room temperature for 2 h, then poured into icecold H20 (50 mL) and extracted with EtOAc (2 x 50 mL). The organic layer was washed with H20 (100 mL) and brine (100 mL). The organic layer was separated, dried over anhydrous Na2SO4 and concentrated in vacuo. The crude residue was purified by column chromatography (silica, 100-200 mesh, 20% EtOAc in hexanes) to afford the title compounds (mixture of isomers; 1.00 g, 82%) as a yellow liquid. ; To a solution of Intermediate 6 (0.25 g, 0.64 mmol) and Intermediate JO (as a mixture of isomers) (0.78 g, 3.23 mmol) in THF (12 mL) was added 1.8M tert-butyl10 lithium solution (1.90 mL, 3.23 mmol) dropwise at -78C. The reaction mixture wasstirred at -78C for 30 minutes and at room temperature for 16 h, then quenched with brine (100 mL) and extracted with EtOAc (2 x 50 mL). The organic layer was separated, and washed with H20 (100 mL) and brine (100 mL), then dried over anhydrous Na2SO4 and concentrated in vacuo. The crude residue was purified by column chromatography(silica, 100-200 mesh, 30% EtOAc in hexanes) to afford the title compound (80% purity by LCMS) (0.12 g, 30%) as a yellow solid. oH (400 MHz, CDC13) 1.58 (m, 9H), 1.92 (s, 3H), 3.25 (s, 3H), 3.72 (d, J 14.1 Hz, 1H), 4.22 (d, J 14.1 Hz, 1H), 6.81 (t, J7.9 Hz, 1H),6.94-7.08 (m, 2H), 7.36 (d, J8.9 Hz, 1H), 7.95 (s, 1H), 8.13 (d, J8.9 Hz, 1H), 10.62 (s, 1H). LCMS (Method 1, ES+) 594 [M+lf?, 3.81 minutes.

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

Reference:
Patent; UCB BIOPHARMA SPRL; DE HARO GARCIA, Teresa; LOWE, Martin Alexander; MACCOSS, Malcolm; TAYLOR, Richard David; ZHU, Zhaoning; (47 pag.)WO2017/144517; (2017); A1;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

Application of 29671-92-9, 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. 29671-92-9, name is Carbamimidic chloride hydrochloride belongs to chlorides-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below.

Example 320 Synthesis of 2-amino-6-(4-fluorophenyl)thieno[2,3-d]pyrimidin-4(3H)-one A mixture of ethyl 2-amino-5-(4-fluorophenyl)thiophene-3-carboxylate (0.3 g, 1.13 mmol), chloroformamidine hydrochloride (0.33 g, 2.83 mmol) and dimethylsulfone (0.53 g, 5.65 mmol) was heated at 120-130 C. for 30 minutes. After cooling down to room temperature, water (10 ml) was added and ammonium hydroxide was used to neutralize the suspension. The solid was filtered off, washed with water and dried. The crude residue was purified by flash chromatography on silica gel (CH2Cl2/MeOH 10:1) to yield the title compound as a white solid (0.28 g, 95%). 1H NMR (300 MHz, DMSO, 25 C.): delta=11.05 (s, 1H, NH), 7.66-7.71 (m, 2H, PhH), 7.51 (s, 1H, CH), 7.23 (t, J=8.8 Hz, PhH), 6.73 (s, 2H, NH2) ppm. HRMS: calcd for C12H9FN3OS 262.04504. found 262.04413.

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, Carbamimidic chloride hydrochloride, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; Katholieke Universiteit Leuven, K.U. Leuven R&D; Herman, Jean; Louat, Thierry; US2014/88088; (2014); 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. 4152-90-3, name is (3-Chlorophenyl)methanamine, A new synthetic method of this compound is introduced below., Safety of (3-Chlorophenyl)methanamine

General procedure: Benzylamine (0.214 g, 2.00 mmol), [VO(PS-BBMA]SO4 (80 mg, 0.08 mmol) and H2O2 (4 mmol) was heated at 80 C for 10 h in a round bottom flask under nitrogen atmosphere. The reaction was monitored by TLC, and after complete consumption of benzylamine, the reaction mixture was cooled to room temperature, filtered and concentrated in vacuo. The residue was purified by column chromatography (ethyl acetate: hexane=1:8) to afford benzamide. The product was analyzed by 1H NMR spectroscopy.

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:
Article; Renuka; Gayathri; Catalysis Communications; vol. 121; (2019); p. 89 – 94;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

Related Products of 54932-72-8, A common heterocyclic compound, 54932-72-8, name is 4-Bromo-1-chloro-2-methylbenzene, molecular formula is C7H6BrCl, 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.

(1) A mixture of 5.00 g (24.3 mmol) of 5-bromo-2-chlorotoluene, 3.56 g (29.2 mmol) of dihydroxyphenylborane, 546mg (2.43 mmol) of palladium acetate (II), 9.41 g (29.2 mmol) of tetrabutylammonium bromide, 8.40 g (60.8 mmol) of potassium carbonate and 50 ml of water was stirred for 5 hours at 80 C. under nitrogen flow. The reaction solution was filtrated through celite, and the filtrate was extracted with ethyl acetate. The organic layer was washed with saturated saline, dried over anhydrous magnesium sulfate, then, concentrated. The residue was subjected to silica gel column chromatography (eluant: hexane) to obtain 3.92 g of 4-chloro-3-methylbiphenyl. 1H-NMR (CDCl3, TMS) delta (ppm): 7.30-7.60 (8H, m), 2.44 (3H, s)

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; Araki, Tomohiro; Kinoshita, Yoshiharu; Sakaguchi, Hiroshi; Manabe, Akio; US2003/119670; (2003); A1;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

Reference of 461432-23-5, 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. 461432-23-5, name is 4-Bromo-1-chloro-2-(4-ethoxybenzyl)benzene belongs to chlorides-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below.

At -78 & lt; 0 & gt; C,A solution of n-butyllithium in n-hexane(120.9 mL, 290 mmol, 7.2 M) was added dropwise2- (4-ethoxyphenyl) methyl-4-bromo-1-chlorobenzene(90 g, 276.3 mmol,Purchased in Shanghai Jinsai Pharmaceutical Company)Of anhydrous tetrahydrofuran(750 mL)After stirring at -78 & lt; 0 & gt; C for 40 min,(3R, 4S, 5R, 6R) -3,4,5-tris (trimethylsiloxy) -6 – [(trimethylsiloxy) methyl] -tetrahydropyran-2-one 1b (141.9 g, 304 mmol)ofAnhydrous tetrahydrofuran(150 mL)The solution was added dropwise to the reaction system.Drop finished,Stirring was continued at -78 & lt; 0 & gt; C for 5 hours.At -78 & lt; 0 & gt; C,The reaction was quenched by the slow addition of 300 mL of saturated ammonium chloride solution, warmed to room temperature and concentrated in vacuo to remove most of the solvent. The residue was added to 450 mLWater, extracted with ethyl acetate (450 mL x 3). The organic phases were combined and washed with saturated brine (600 mL) and dried over anhydrous sodium sulfateThe filtrate was concentrated under reduced pressure to give the title compound lc (208.9 g, pale yellow oil) in 100% yield. Crude productDirectly for the next step.

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

Reference:
Patent; Beijing Zhonghaikang Pharmaceutical Co., Ltd.; Zhou Di; Lin Fengwei; Jiao Shuang; Wen Bo; Huang Hai; (29 pag.)CN106674245; (2017); A;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics