Author: Jessica.F

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. 104-11-0, name is 1-(4-Chlorophenyl)-N-methylmethanamine, This compound has unique chemical properties. The synthetic route is as follows., Recommanded Product: 1-(4-Chlorophenyl)-N-methylmethanamine

General procedure: A solution of 0.17g (1.40mmol) of N-benzylmethylamine, 0.20g (1.40mmol) of K2CO3 and 0.40g of (R,S)-3(4-bromobutyl)-5-phenyloxazolidin-2-one 23 in ACN was allowed to stirring under reflux for 6-12h and monitored by TLC until the reaction was completed. The hot solution was filtered and concentrated in vacuo to afford 0.29g (85.0mmol) of a chromatography pure yellow oil 2a.

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 104-11-0.

Reference:
Article; Zampieri, Daniele; Vio, Luciano; Fermeglia, Maurizio; Pricl, Sabrina; Wuensch, Bernhard; Schepmann, Dirk; Romano, Maurizio; Mamolo, Maria Grazia; Laurini, Erik; European Journal of Medicinal Chemistry; vol. 121; (2016); p. 712 – 726;,
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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. 27139-97-5, name is 2-Bromo-4-chloro-1-methylbenzene, This compound has unique chemical properties. The synthetic route is as follows., category: chlorides-buliding-blocks

An agitator provided, 200 ml of a Schlenk tube substd. argon, as shown in the above-mentioned chemical eq. (116) 2-bromo-4-chlorotoluene (5. 02g, 20. A 0mmol) and diethyl ether (50 ml), stirring, -15 ¡ã C are cooled. There, 1. ¡¤ Phenylbicyclohexane soln. 6M-n-butyl lithium (13. 0 ml, 20. 5mmol) is dropped. 1 period, trimethyl borate (2. 13g, 20. 5mmol) is added, while warming up to a room temperature, a cooling bath is removed from 15¡ã C-, 18 hours. By adding distilled water (20 ml) little by little, the reaction is stopped, and diethyl ether Phenylbicyclohexane under reduced pressure is removed.

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 27139-97-5.

Reference:
Patent; NIPPON HOSO KYOKAI <NHK>; KANTO CHEM CO INC; FUKAGAWA HIROHIKO; SHIMIZU TAKAHISA; TAKAHASHI JUNPEI; SHINNAI SATONOBU; TSUCHIYA KAZUHIKO; (53 pag.)JP2015/160849; (2015); A;,
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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. 106-39-8, name is 1-Bromo-4-chlorobenzene, This compound has unique chemical properties. The synthetic route is as follows., Recommanded Product: 1-Bromo-4-chlorobenzene

General procedure: A 50 mL round-bottomed flask, equipped with a gas inlet tube, a refluxcondenser and a magnetic stirring bar was charged with MCM-41-2PPdCl2 (102 mg, 0.05 mmol Pd), aryl halide (5.0 mmol) and HCOONa(7.5 mmol). The flask was flushed with CO. DMF (5 mL) was addedby syringe and a slow stream of CO was passed into the suspension.The mixture was vigorously stirred at 110-130 C for 2-20 h, cooledto room temperature and diluted with diethyl ether (50 mL). Thepalladium catalyst was separated from the mixture by filtration,washed with distilled water (2 ¡Á 10 mL), ethanol (2 ¡Á 10 mL) and ether(2 ¡Á 10 mL) and reused in the next run. The ethereal solution waswashed with water (3 ¡Á 20 mL), and dried over anhydrous magnesiumsulfate and concentrated under reduced pressure. The residue waspurified by flash column chromatography on silica gel (hexane-ethylacetate = 10 : 1).

According to the analysis of related databases, 106-39-8, the application of this compound in the production field has become more and more popular.

Reference:
Article; Jiang, Jianwen; Wang, Pingping; Cai, Mingzhong; Journal of Chemical Research; vol. 38; 4; (2014); p. 218 – 222;,
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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;,
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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;,
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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,
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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;,
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Chlorides – an overview | ScienceDirect Topics