Month: June 2021

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. 97329-43-6, name is 1-Bromo-2-chloro-3-methylbenzene, A new synthetic method of this compound is introduced below., Quality Control of 1-Bromo-2-chloro-3-methylbenzene

A mixture of 1-bromo-2-chloro-3-methylbenzene (4.0 g, 19.6 mmol), Pd2dba3 (1014 mg, 0.98 mmol), Xantphos (566 mg, 0.98 mmol), tert-butyl carbamate (3.41 g, 29.4 mmol) and Cs2CO3 (9.58 g, 29.4 mmol) in dioxane (120 mL) was stirred at 110 C. for 2 h and then cooled to rt. Water (150 mL) was added and the mixture was extracted by EtOAc (150 mL×2). The organic layer was dried and concentrated. The residue was purified by flash column chromatography (PE , 100%) to afford the title compound (4.2 g, 89%). MS (ES+)C12H16ClNO2 requires: 241, found: 187 [M-55+H]+.

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; BOARD OF REGENTS, THE UNIVERSITY OF TEXAS SYSTEM; JONES, Philip; CZAKO, Barbara; CARROLL, Christopher L.; MANDAL, Pijus; CROSS, Jason; (64 pag.)US2020/48249; (2020); A1;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

These common heterocyclic compound, 104-52-9, name is 3-Phenylpropyl Chloride, 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. Application In Synthesis of 3-Phenylpropyl Chloride

(1) 1-Bromo-3-chloro-1-phenylpropane 3-Chloro-1-phenylpropane (3.09 g, 20 mmol.), N-bromosuccinimide (3.56 g, 20 mmol.), benzoyl peroxide (catalytic amount), and carbon tetrachloride (30 mL) were mixed, and the resulting mixture was heated to reflux for 15 min while it was exposed to a light of 100V/100 W, to perform a reaction. Insolubles were filtered off. The reaction liquid was washed with an aqueous saturated sodium hydrogen carbonate solution and an aqueous saturated sodium chloride solution, dried over anhydrous sodium sulfate, and placed under reduced pressure to distill the solvent off, to give 4.58 g of the desired compound (yield 98%) as an oil. 1 H-NMR (CDCl3) delta: 2.1-2.9 (2H, m), 3.3-3.9 (2H, m), 5.16 (1H, dd, J=7 Hz, 10 Hz), 7.1-7.5 (5H, m).

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

Reference:
Patent; Nippon Chemiphar Co., Ltd.; US5773437; (1998); A;,
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. 461432-23-5, name is 4-Bromo-1-chloro-2-(4-ethoxybenzyl)benzene, A new synthetic method of this compound is introduced below., Safety of 4-Bromo-1-chloro-2-(4-ethoxybenzyl)benzene

Accurately weigh 65.12g (0.2Mol) of raw material A, then add toluene / tetrahydrofuran mixture (V toluene / tetrahydrofuran = 2:1), dilute to 500ml, mix and pump into the microreactor at a flow rate of 14ml / min a reaction unit,At the same time, the concentration of 2.0mol / L n-butyl lithium solution was pumped into the first reaction unit at a flow rate of 3.4ml / min for thorough mixing to produce lithium halide exchange reaction, the residence time was 27 seconds, and the reaction temperature was controlled at -15 C. After the reaction solution flows out of the first reaction unit,At the same time, the raw material C was flowed into the second reaction unit of the microreactor at a flow rate of 2.2 ml/min to carry out a lactone condensation reaction.The residence time of the reaction in this step was 22 seconds, and the reaction temperature of the second reaction unit was controlled to be -15 C. Accurately prepare a mixture of 300 ml of methanol and methanesulfonic acid (V methanol / methanesulfonic acid = 4:1),It is pumped into the third reaction unit of the microreactor at a flow rate of 3.5 ml/min, and mixed with the reaction liquid flowing out from the second reaction unit.The residence time of the reaction in this step is 19 seconds, and the reaction temperature controlled by the reaction unit is 5 C. After the reaction liquid flows out from the third reaction unit,At the same time, the prepared mixture of boron trifluoride diethyl ether and triethylsilane was pumped into the fourth reaction unit at a flow rate of 3.5 ml/min.The residence time of the reaction unit is 15 seconds, the temperature of the fourth reaction unit is controlled to be 5 C, and the liquid discharged from the fourth reaction unit is continuously collected 100 ml.Finally, it was added to 200 ml of n-heptane, stirred and crystallized, and kept at 0 C for 1 hour, and filtered to obtain a crude product of dapagliflozin.

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; Shandong Heroic Chemical Co., Ltd.; Ning Jiabin; Ren Miaomiao; Ge Yuan; Wang Wei; Sheng Zhen; Zheng Hao; (12 pag.)CN109400561; (2019); A;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

Application of 13726-14-2, 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. 13726-14-2, name is 4-Chloro-3-methoxyaniline belongs to chlorides-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below.

Step-1: N-(4-chloro-3-methoxyphenyl)acetamide [0112] To a solution of 4-chloro-3-methoxyaniline (50 g, 317 mmol) and DIPEA (110 mL, 635 mmol) in CH2Cl2 (700 mL) was added acetic anhydride (36 mL, 381 mmol) drop wise at 0 C and the reaction mixture was stirred at room temperature for 3 h. The reaction then was quenched with water (250 mL) and the organic layer was separated. The aqueous layer was extracted with CH2Cl2 (100 mL x 3). The combined organic layers were dried (Na2SO4), concentrated and purified by flash chromatography with CH2Cl2/MeOH to give N- (4-chloro-3-methoxy phenyl)acetamide (71 g, quantitative yield) as a white solid.

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, 4-Chloro-3-methoxyaniline, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; FORMA THERAPEUTICS, INC.; ASHWELL, Susan; CAMPBELL, Ann-Marie; CARAVELLA, Justin Andrew; DIEBOLD, R. Bruce; ERICSSON, Anna; GUSTAFSON, Gary; LANCIA, David R.; LIN, Jian; LU, Wei; WANG, Zhongguo; (147 pag.)WO2016/171755; (2016); A1;,
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. 14752-66-0, name is Sodium 4-chlorobenzenesulfinate, This compound has unique chemical properties. The synthetic route is as follows., Quality Control of Sodium 4-chlorobenzenesulfinate

General procedure: The 2a (0.6 mmol), UiO-67-Ru (2.0 mg), and nitrobenzene (0.4 mmol) were added to a clear-colored glass vial equipped with a stir bar. Then DMF : H2O (3:1, 2 mL) were added, followed by 1a (0.2 mmol). The reaction was stirred at room temperature under blue LEDs (3 W) for 21 h, until the raw materials completely disappeared by TLC. After the reaction was finished, water was added and the mixtures were extracted with ethyl acetate (20 mL * 4). The combined organic layer was washed with water (10 mL * 3), brine (10 mL * 3), dried over anhydrous Na2SO4. The filtrate was concentrated under reduced pressure. The obtained residue was chromatographed on a silica gel column eluted with PE : DCM : EA = 3:3:1 to afford the desired 3.

According to the analysis of related databases, 14752-66-0, the application of this compound in the production field has become more and more popular.

Reference:
Article; Kong, Hao; Xu, Siyan; Zhang, Ronghua; Tetrahedron Letters; (2020);,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

Adding a certain compound to certain chemical reactions, such as: 452-83-5, name is 2-Chloro-5-fluoroaniline, 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 452-83-5, category: chlorides-buliding-blocks

General procedure: A mixture of 2-bromostyrene (549mg, 3.00mmol), the appropriate 2-chloroaniline derivative (3.00mmol), Pd(dba)3 (68mg, 0.075mmol), DavePhos (79mg, 0.20mmol), and NaOtBu (864mg, 9.00mmol) in dry 1,4-dioxane (10mL) was stirred under a N2 atmosphere at 115C for 6h. After it had been cooled down to rt, EtOAc (150mL) was added. The mixture was washed with water (5×150mL) and subsequently with brine (150mL). The organic phase was separated and dried over MgSO4. After evaporation of the solvent, the residue was submitted to column chromatography (SiO2, eluent: petroleum ether/EtOAc 20:1). The yellow fraction was collected, and evaporation of the eluent in vacuo gave the desired product.

At the same time, in my other blogs, there are other synthetic methods of this type of compound, 2-Chloro-5-fluoroaniline, and friends who are interested can also refer to it.

Reference:
Article; Tian, Maoqun; Abdelrahman, Aliaa; Weinhausen, Stephanie; Hinz, Sonja; Weyer, Stefanie; Dosa, Stefan; El-Tayeb, Ali; Mueller, Christa E.; Bioorganic and Medicinal Chemistry; vol. 22; 3; (2014); p. 1077 – 1088;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

These common heterocyclic compound, 104-52-9, name is 3-Phenylpropyl Chloride, 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. category: chlorides-buliding-blocks

General procedure: To a suspension of alkyl halide (1 mmol) and nucleophilic reagents(NaOAc or KSCN) (2 mmol) in water (5 mL), Fe3O4SiO2/DABCO(0.225 g) was added and the mixture was stirred at 90 C for the lengths of time shown in Table 1. After completion of the reaction as indicated by TLC [using n-hexane/ethyl acetate (5:1)], the reaction was allowed to cool to room temperature and the magnetic catalyst was concentrated on the side wall of the reaction vessel using an external magnet. The reaction mixture residue was poured into water (10 mL)and extracted with EtOAc (3 × 10 mL). The combined organic layers were dried over anhydrous Na2SO4, filtered and evaporated in vacuo to give the product in 74% to 91% isolated yields.

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

Reference:
Article; Davarpanah, Jamal; Kiasat, Ali Reza; Catalysis Communications; vol. 42; (2013); p. 98 – 103;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

Synthetic Route of 220227-21-4, 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. 220227-21-4, name is 2,4,5-Trifluorobenzene-1-sulfonyl chloride belongs to chlorides-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below.

To a stirred solution of 4-chlorophenol (13.94 g, 108 mmol) in tetrahydrofuran (400 mL) at ambient temperature was added triethylamine (30.2 mL, 216 mmol). The mixture was stirred at ambient temperature for 10 minutes and cooled to 0 C. 2,4,5-Trifluorobenzenesulfonyl chloride (25.00g, 108 mmol) was added and the reaction mixture was stirred for 1 h at ambient temperature and diluted with ethyl acetate (600 mL) and water (200 mL). The organic layer was washed with brine, dried over anhydrous sodium sulfate and filtered. The filtrate was concentrated in vacuo to afford 4-chlorophenyl 2,4,5-trifluorobenzenesulfonate as a colorless liquid in 98% yield (34.4 g): 1H NMR (300 MHz, DMSO-cfe) £8.18-7.96 (m, 2H), 7.50 (d, J = 7.2 Hz, 2H), 7.19 (d, J = 7.2 Hz, 2H).

The synthetic route of 2,4,5-Trifluorobenzene-1-sulfonyl chloride has been constantly updated, and we look forward to future research findings.

Reference:
Patent; XENON PHARMACEUTICALS INC.; LIU, Shifeng; FOCKEN, Thilo; CHAHAL, Navjot; ZHANG, Zaihui; OBALLA, Renata, Marcella; FONAREV, Julia; WO2013/64984; (2013); 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. 261762-56-5, name is 1-Chloro-2-fluoro-3-methoxybenzene, A new synthetic method of this compound is introduced below., HPLC of Formula: C7H6ClFO

To a 0 C solution of 1-chloro-2-fluoro-3-methoxybenzene (1.606 g, 10 mmol) in acetic acid (5.00 ml) was added fuming nitric acid (0.93 3 ml, 20.00 mmol) followed bythe dropwise addition of sulfuric acid (2.132 ml, 40.0 mmol). After 30 mm, the reaction mixture was poured into water and diluted with ethyl acetate. The organic phase was separated and washed 2x with saturated NaHCO3 followed by a final brine wash. The organic solution was then dried over Mg504, filtered, concentrated and purify by ISCO (120g, 10-50% EtOAc/Hexanes, 25 mm. Desired regioisomer eluted second) affordingIntermediate I-43A (1.lOg, 5.35 mmol, 53% yield) as a yellow solid. LC-MS: Method H,RT = 1.13 mm, MS (ESI) m/z: No Ionization Observed (M+H)t ?H NMR (400MHz, CHLOROFORM-d) oe 7.89 (dd, J=9.2, 2.2 Hz, 1H), 6.95 (dd, J=9.4, 7.6 Hz, 1H), 4.00 (s, 3H). Regiochemistry confirmed through NMR analysis of both regioisomeric products.

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; BRISTOL-MYERS SQUIBB COMPANY; ZHANG, Xiaojun; PRIESTLEY, Eldon Scott; BATES, J. Alex; HALPERN, Oz Scott; REZNIK, Samuel Kaye; RICHTER, Jeremy M.; (1137 pag.)WO2018/13774; (2018); A1;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

623-12-1, name is 1-Chloro-4-methoxybenzene, 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. category: chlorides-buliding-blocks

General procedure: 1.0 mol%), KOtBu (224.4 mg, 2.0 mmol), toluene (1.0 mL), ketones3 (2.0 mmol or 0.7 mmol), and aryl chlorides 2 (1.0 mmol) weresuccessively added into a Schlenk reaction tube. The mixture wasstirred at the specified temperature for the listed time shown inTables 1-3. The reaction mixture was cooled to room temperature,then the solvent was evaporated under reduced pressure and theresidue was purified by flash column chromatography to give thepure products.

The synthetic route of 623-12-1 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Xiao, Zheng-Kang; Yin, Hui-Ying; Lu, Jian-Mei; Inorganica Chimica Acta; vol. 423; PART A; (2014); p. 106 – 108;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics