Chlorides-buliding-blocks

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. 13918-92-8, name is 2,4-Difluorobenzene-1-sulfonyl chloride, A new synthetic method of this compound is introduced below., Product Details of 13918-92-8

2,4-Difluorobenzenesulfonyl chloride (4 g, 18.81 mmol) in DCM (10 mL) was added slowly to a solution of 2-(methylamino)ethanol (1.66 mL, 20.70 mmol) in DCM (200 mL) and 10% sodium hydroxide solution (200 mL) at O0C. The reaction was allowed to warm to RT and stirred for 20 hours. The DCM layer was separated and the aqueous re-extracted into DCM (2 x 50 mL). The combined organics were washed with brine, dried (MgSO4), filtered and reduced in vacuo to give the desired compound as a colourless oil (4.7 g). 1H NuMR delta (CDCl3): 1.98 (t, IH), 2.94 (s, 3H), 3.32 (t, 2H), 3.79 (q, 2H), 6.94 – 7.03 (m, 2H), 7.89 – 7.95 (m, IH)

The synthetic route of 13918-92-8 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; ASTRAZENECA AB; ASTRAZENECA UK LIMITED; WO2006/125972; (2006); A1;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

These common heterocyclic compound, 367-22-6, name is 4-Chloro-3-fluoroaniline, 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. COA of Formula: C6H5ClFN

Description 45 (78 mg, 0.37 mmol) and 3-fluoro-4-chloroaniline (54 mg, 0.37 mmol) inMeCN (2 ml) in the presence of a catalytic quantityof DMAP were stirred at 45 C for 16 h. The reaction was cooled and the resultant solid collected by filtration and rinsed with ether. Without further purification this solid was added to sodium hydroxide solution(1 % aqueous w/w, 2 ml) and heated at 80 OC for 30 min. The reaction was cooled, filtered throughCeliteX to remove insoluble impurities and the filtrate was acidified to pH-6 by the dropwise addition of hydrochloric acid (5N) to precipitate the product. The solid was collected by filtration, rinsed with water then ether and dried to give the title compound (70 mg). 1H NMR (400 MHz, DMSO)8 7.86(1H, s), 7.70(1H, t, J8.4), 7.43(1H, dd,J2. 2,10. 0), 7.14-7. 12(1H, m),3. 77 (3H, s) ;Mlz (ES+) 313,311 (M+H+).

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

Reference:
Patent; MERCK SHARP & DOHME LIMITED; HOLLINGWORTH, Gregory, John; JONES, A., Brian; SPAREY, Timothy, Jason; WO2005/49613; (2005); A1;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

Application of 626-43-7, A common heterocyclic compound, 626-43-7, name is 3,5-Dichloroaniline, molecular formula is C6H5Cl2N, 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.

In a reaction flask, 48 g (0.3 mol) of 3,5-dichloroaniline was added to a mixed solution of 500 mL of water and 500 mL of hydrochloric acid.Medium, after stirring evenly, cool down to 0 C,Under stirring, 400 mL of an aqueous solution containing 23 g (0.34 mol) of sodium nitrite was added dropwise, and after mixing, the mixture was uniformly mixed to obtain a solution A;1000 mL of an aqueous solution containing 67 g (1.2 mol) of potassium hydroxide was placed in another reaction flask.Under the condition of 0 C, slowly add 250 mL of ethanol (35 mol) dissolved in ethyl pyruvate, and then add to the solution B after stirring.After the solution A was brought to a temperature of 0 C, the solution B was slowly added dropwise to the solution A, and after the completion of the dropwise addition, the temperature was raised to 40 C for 10 minutes, and then the reaction solution was extracted three times with 1000 mL of diethyl ether.The organic phases were combined, dried over anhydrous magnesium sulfate (100 g), concentrated, and then recrystallized from a mixture of n-hexane and acetone (V-hexane: Vacetone = 2:1) to give ethyl-2-(2-(3,5-) Chlorophenyl)indenyl)propionic acid 78g,Yield is 95%

The synthetic route of 626-43-7 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Henan Wanliu Biological Technology Co., Ltd.; Yang Weixiao; Ren Baoqi; Wang Jiahao; (13 pag.)CN108864089; (2018); A;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

Electric Literature of 108649-59-8, 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. 108649-59-8 name is 1-(2-Bromoethyl)-2,4-dichlorobenzene, 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.

General procedure: Magnesium turnings (13.2 g, 0.55 mol) were placed in dry THF (25 mL) undernitrogen. A small amount (10 mL) of (2-bromoethyl)benzene (92.5 g, 0.50 mol) dissolvedin dry THF (300 mL), added to the magnesium slurry and stirred for a few minutes withwarming until the reaction commenced. The remainder of the (2-bromoethyl)benzenesolution was added dropwise to maintain reflux over an hour, then the reaction mixturewas aged at reflux for an additional an hour. The reaction mixture was cooled to 25 C. In a separate flask, diethyl oxalate (88.2 g, 0.6 mol) was dissolved in dry THF (100mL) and cooled to -10 C. The supernatant solution of (2-phenylethyl)magnesiumbromide was sucked under nitrogen through a sintered-glass filter into a dropping funnel.The reaction temperature was held at -10 C as the solution of Grignard reagent wasadded dropwise over an hour to the diethyl oxalate. The sintered-glass funnel anddropping funnel were then rinsed with dry THF (100 mL), and the rinse was added to thebatch. The reaction mixture was allowed to stand for 30 min and then quenched byaddition of 3 M HCl (145 mL).Hexane (500 mL) was added, and the aqueous layer was discarded. The organicphase was washed with brine (100 mL) and saturated NaHCO3 (100 mL), until theaqueous layer measured to pH 5.0. The organic phase was dried with anhydrous Na2SO4.Filtered and washed with hexane, and the combined layers were concentrated to an oil invacuum. The crude keto ester (103.0 g) was vacuum distilled at 105-110 C (0.2-0.3 mmHg) to afford a colourless oil 90.0 g with 60% yield.

At the same time, in my other blogs, there are other synthetic methods of this type of compound, 1-(2-Bromoethyl)-2,4-dichlorobenzene, and friends who are interested can also refer to it.

Reference:
Article; Zhu, Lufeng; Chen, Houhe; Meng, Qinghua; Fan, Weizheng; Xie, Xiaomin; Zhang, Zhaoguo; Tetrahedron; vol. 67; 34; (2011); p. 6186 – 6190;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

Reference of 468075-00-5,Some common heterocyclic compound, 468075-00-5, name is 2-Bromo-1-chloro-4-(trifluoromethoxy)benzene, molecular formula is C7H3BrClF3O, 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-bromo-l-chloro-4-(trifluoromethoxy)benzene (5.00 g, 18.15 mmol), Pd(dppf)Cl2.CH2Cl2 (1.48 g, 1.82 mmol) and Et3N (5.51 g, 54.45 mmol) in EtOH (30 mL) was degassed, and refilled with CO. The reaction was stirred under CO (50 psi) for 16 hours at 80 C, at which point the desired product was observed by LCMS. The reaction mixture was diluted with EtOH (20 mL), and filtered through a Celite pad. The filtrate was concentrated. The residue was purified by flash chromatography on silica gel (EtOAc in PE = 0% 5%) to afford compound 12-b (2.40 g, 8.93 mmol) as an oil. 1H NMR (400MHz, CDC13) deltaH = 7.66 – 7.59 (m, 1H), 7.42 (d, 1H), 7.24 – 7.19 (m, 1H), 4.36 (q, 2H), 1.35 (t, 3H).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 2-Bromo-1-chloro-4-(trifluoromethoxy)benzene, its application will become more common.

Reference:
Patent; PRAXIS PRECISION MEDICINES , INC.; REDDY, Kiran; MARTINEZ BOTELLA, Gabriel; GRIFFIN, Andrew, Mark; MARRON, Brian, Edward; (244 pag.)WO2018/148745; (2018); A1;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

Electric Literature of 13918-92-8, A common heterocyclic compound, 13918-92-8, name is 2,4-Difluorobenzene-1-sulfonyl chloride, molecular formula is C6H3ClF2O2S, 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.

Reference Example 143; tert-butyl ({5- (2-cyanopyridin-3-yl) -l-[ (2,4- difluorophenyl) sulfonyl] -lH-pyrrol-3-yl}methyl)methylcarbamate; To a suspension of sodium hydride (60% in oil, 26.0 mg) in tetrahydrofuran (3 mL) was added tert-butyl {[5- (2- cyanopyridin-3-yl) -lH-pyrrol-3-yl]methyl Jmethylcarbamate (156 mg) at room temperature, and the mixture was stirred for 15 min. After stirring, 15-crown-5 (143 mg) and 2,4- difluorobenzenesulfonyl chloride (159 mg) were added dropwise and the mixture was further stirred at room temperature for 1 hr. Saturated aqueous ammonium chloride solution was added, and the mixture was concentrated under reduced pressure. The residue was extracted with ethyl acetate. The separated aqueous layer was extracted again with ethyl acetate. The combined organic layer was washed with saturated brine, dried over anhydrous magnesium sulfate, and concentrated under reduced pressure. The residue was purified by silica gel column chromatography (eluent: hexane-ethyl acetate=9: 1-*2: 1) to give the title compound as a colorless oil (yield 208 mg, 85%).1H-NMR (CDCl3) delta: 1.48(9H,s), 2.85 (3H,brs) , 4.29 (2H,brs) , 6.46(lH,brs) , 6.80-6.88 (IH,m) , 6.93 (lH,ddd, J=IO.2, 8.1, 2.4Hz) , 7.20(lH,ddd, J=8.8, 8.0, 5.8Hz) , 7.46 (IH, s) , 7.55(lH,dd, J=7.9,4.7Hz) , 7.93 (IH, dd, J=8.0, 1.6Hz) , 8.69(lH,dd, J=4.7,1.7Hz) .

The synthetic route of 13918-92-8 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; TAKEDA PHARMACEUTICAL COMPANY LIMITED; WO2008/108380; (2008); A2;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

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. 7006-52-2, name is N-Methyl-3-chloroaniline, This compound has unique chemical properties. The synthetic route is as follows., COA of Formula: C7H8ClN

General procedure: Bi(NO3)3.5H2O (2 equiv, 0.6 mmol), Pd(OAc)2 (0.015 mmol, 5 mol percent) were added into a 25mL oven-dried Schlenk tube, the tube was evacuated and backfilled with Ar (repeated three times in 30 min). Under a counter flow of Ar, N-substituted aniline (1 equiv, 0.3 mmol) was added by syringe firstly, 1.5 mL TFE and 0.5 mL TFA were then added by disposable medical syringes. The flask was sealed and the mixture was stirred firstly at room temperature for15 min, then allowed to stir in a preheated oil bath at 90 °C for 24 h.The mixture was cooled to room temperature when the reaction was completed. Next, the solution was diluted by 10 mL ethyl acetate and filtered the insoluble matters, washed the organic phases by 5percent NaHCO3 solution after the extraction, and extracted the aqueous phases by ethyl acetate (3×15 mL) to collect organic phases. All the organic solutions were washed by brine, dried 30 min with anhydrous MgSO4, filtered and concentrated under reduced pressure. The crude products were purified by chromatography on silica gel, eluting with ethyl acetate/petroleum ether(5/1-2/1).

According to the analysis of related databases, 7006-52-2, the application of this compound in the production field has become more and more popular.

Reference:
Article; Feng, Yi-Si; Mao, Long; Bu, Xiao-Song; Dai, Jian-Jun; Xu, Hua-Jian; Tetrahedron; vol. 71; 23; (2015); p. 3827 – 3832;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

Synthetic Route of 445-13-6, 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. 445-13-6, name is 3-Chloro-4-(trifluoromethyl)aniline belongs to chlorides-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below.

To a solution of triphosgene (609 mg, 2.14 mmol) in toluene (5 mL) was added dropwise a solution of 3-chloro-4-(trifluoromethyl)aniline (100 mg, 0.51 mmol) and refluxed at 80 C for 0.5 h. Then the mixture was concentrated to give crude 2-chloro-4- isocyanato-l-(trifluoromethyl)benzene used in the next step without purification. To the solution of 2-chloro-4-isocyanato-l-(trifluoromethyl)benzene in THF was added (S)-3-(5- (aminomethyl)-l-oxoisoindolin-2-yl)azepane-2,7-dione (TFA salt) (59.1 mg, 0.21 mmol), followed by TEA (42 mg, 0.42 mmol). The mixture was stirred at RT for 2 h. The mixture was concentrated and purified by silica gel chromatography eluting with MeOH/DCM from 0% to 8% to give Compound 12 (29.4 mg, 28%) as a white solid. MS (ESI) m/z 509.0 [M+H]+. MR (400 MHz, DMSO-d6) delta 10.72 (s, 1 H), 9.36 (s, 1 H), 7.91 (s, 1 H), 7.70- 7.68 (m, 2 H), 7.54 (s, 1 H), 7.45-7.41 (m, 2 H), 7.06 (t, J =14 Hz, 1 H), 5.23 (dd, J =7.6, 12.8 Hz, 1 H), 4.52 (s, 2 H), 4.43 (d, J =6.0 Hz, 2 H), 3.12-3.04 (m, 1 H), 2.61-2.55 (m, 1 H), 2.28-2.22 (m, 1 H), 2.12-1.96 (m, 2 H), 1.84-1.76 (m, 1 H).

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-(trifluoromethyl)aniline, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; BIOTHERYX, INC.; MERCURIO, Frank; CHAN, Kyle, W.H.; SULLIVAN, Robert; ERDMAN, Paul, E.; FUNG, Leah; (105 pag.)WO2018/169777; (2018); A1;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

Synthetic Route of 108-41-8, These common heterocyclic compound, 108-41-8, name is 1-Chloro-3-methylbenzene, 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.

General procedure: A dried round bottomed flask equipped with a magnetic stir bar was charged with 15 mg Polymer anchored-Pd(II) C catalyst (PS-8-AQ-Pd), 2-phenyl pyridine (0.5 mmol), benzyl alcohol (1.0 mmol)and TBHP (2.0 mmol) were added to a reaction vessel. The mixture was stirred at 110 C for 8 h, then cooled to room temperature and catalyst was filtered, the filtrate was extracted with ethyl acetate(3 10 mL). The combined organic layers were extracted with water, and dried over anhydrous Na2SO4. The organic layers were evaporated under reduced pressure and the resulting crude product was purified by column chromatography by using ethylacetate/hexane (1:4) as eluent to give the corresponding ortho acylation products. The products were characterized by 1H NMR,13C NMR and HRMS.

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

Reference:
Article; Perumgani, C. Pullaiah; Parvathaneni, Sai Prathima; Kodicherla, Balaswamy; Keesara, Srinivas; Mandapati, Mohan Rao; Inorganica Chimica Acta; vol. 455; (2017); p. 105 – 111;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

Electric Literature 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.

2-Dimethylaminoethyl chloride hydrochloride (0.97 g, 6.70 mmol) was added to a mixture of 4-(4,4,5,5-tetramethyl-1 ,3,2-dioxaborolan-2-yl)-1 H-pyrazole (1 .00 g, 5.15 mmol) and caesiumcarbonate (5.54 g, 17.01 mmol) in dry N,N-dimethylformamide (20 mL) at 0C. After stirring for30 mm the ice-water bath was removed. The reaction mixture was stirred at room temperaturefor three days. The reaction mixture was diluted with ethyl acetate (150 mL) and washed with brine (3×100 mL). The organic layer was dried with sodium sulfate and concentrated in vacuo to afford 1 .00 g (3.41 mmol; 66% of theory) of the title compound.GO-MS (Method L9): R1 = 4.48 mm; (no mass detected)1 H NMR (300 MHz, Chloroform-d, Method M2) 6 7.78 (s, 1 H), 7.74 (s, 1 H), 4.23 (t, J = 6.8 Hz,2H), 2.76 (t, J = 6.8 Hz, 2H), 2.26 (s, 6H), 1.31 (s, 12H).

The synthetic route of 4584-46-7 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; BAYER ANIMAL HEALTH GMBH; KOeHLER, Adeline; WELZ, Claudia; BOeRNGEN, Kirsten; KULKE, Daniel; ILG, Thomas; KOeBBERLING, Johannes; HUeBSCH, Walter; SCHWARZ, Hans-Georg; GOeRGENS, Ulrich; EBBINGHAUS-KINTSCHER, Ulrich; HINK, Maike; NENNSTIEL, Dirk; RAMING, Klaus; ADAMCZEWSKI, Martin; BOeHM, Claudia; (269 pag.)WO2017/178416; (2017); A1;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics