Author: Jessica.F

Reference of 6480-66-6,Some common heterocyclic compound, 6480-66-6, name is 2,6-Dichloro-4-methoxyaniline, molecular formula is C7H7Cl2NO, 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.

Trichloromethyl carbonochloridic acid ester (0.0065 mol) was added to the solution of 2,6-dichloro-4-methoxybenzenamine (0.001 mol) and Et3N (0.4 ml) in dry toluene (16 ml). The reaction mixture was stirred for 2 hours at 6O0C till the starting aniline reacted completely (control by TLC). Then, a solution of intermediate 24 (prepared according to A8.c) in DCM (4 ml) was added to the reaction mixture at 6O0C at stirring. Formation of precipitate was observed. The stirring was continued at 60-70C for 1 hour. Then, the reaction mixture was concentrated in vacuum. The formed sediment was treated with water and filtered off. Then, it was washed with water, ethyl acetate, ether, and dried on the air. Yield: 0.360 g of compound 15 (66 %).

The synthetic route of 6480-66-6 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; JANSSEN PHARMACEUTICA N.V.; WO2008/148868; (2008); A1;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

Related Products of 90390-33-3, 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. 90390-33-3 name is 3-Chloro-5-fluorobenzylamine, 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.

Weigh 159 mg of 3-chloro-5-fluorobenzylamine (1 mmol) in a dry 50 mL eggplant-shaped reaction flask, add 15 mL of dichloromethane, and stir until the substrate is completely dissolved.After adding 200 muL of triethylamine, 192 mg of (E) oct-6-enoyl chloride (1.2 mmol) dissolved in an appropriate amount of dry dichloromethane) was slowly added dropwise under an ice bath at 0 to 5 C.After the completion of the dropwise addition, the TLC tracking and monitoring were carried out at room temperature, and when the raw materials disappeared, 20 mL of saturated sodium hydrogencarbonate was sequentially used.The water and the saturated aqueous NaCl solution were each washed three times and dried over anhydrous sodium sulfate.The mixture was separated by silica gel column chromatography under reduced pressure to give (E)-N-(3-chloro-5-fluorobenzyl)oct-6-enamide.

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

Reference:
Patent; Shanghai Shidande Biological Co., Ltd.; Shanghai Shidande Criterion Technology Services Co., Ltd.; Qian Yong; Xin Zhenqiang; Shu Yaping; Zhang Tianyong; Xie Tianpei; (11 pag.)CN108503559; (2018); 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. 200190-87-0, name is 1-Bromo-4-chloro-2-fluoro-5-methylbenzene, A new synthetic method of this compound is introduced below., Application In Synthesis of 1-Bromo-4-chloro-2-fluoro-5-methylbenzene

(2) Ether solution (45mmol) containing the compound prepared by the method of the Reference Example 9 (1) (3.15g, 14mmol) was stirred at -78?C, followed by dropwise addition of n-butyl lithium (1.6M in hexane, 10.2ml, 16mmol) over 10 minutes, and the stirring was continued at the same temperature for 30 minutes. Then, trimethyl borate (1.77g, 17mmol) in ether (8ml) was dropwise added at the same temperature over 10 minutes, and the resulting mixture was stirred for 3 hours at the same temperature. The temperature of the mixture was gradually increased to the room temperature by standing overnight. 1N hydrochloric acid (50ml) was added with ice cooling and the mixture was stirred at room temperature for 1 hour. The ether layer was separated, and the aqueous layer was extracted with ether. The ether layers were combined, washed with brine, dried and concentrated by evaporation of the solvent. A small amount of petroleum ether was added to the residue, followed by filtration of deposited crystals. The crystals were dried to obtain 4-chloro-2-fluoro-5-methylphenylboronic acid (2.94g). m.p.250-253?C 1H-NMR(DMSO-d6) delta 2.29(3H, s), 7.23(1H, d, J=8.8Hz), 7.50(1H, d, J=6.6Hz), 8.23(2H, br s) 19F-NMR(DMSO-d6) delta -106.1 IR(Nujol) 3360, 1608, 1568, 1235, 1132, 1045, 944, 795 cm-1

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; Sumitomo Chemical Takeda Agro Company, Limited; EP1333029; (2003); A1;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

Adding a certain compound to certain chemical reactions, such as: 202865-57-4, name is 1-Bromo-2,5-dichloro-3-fluorobenzene, 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 202865-57-4, Safety of 1-Bromo-2,5-dichloro-3-fluorobenzene

6-chloro-2-fluoro-3-methylphenol (3.3 g, 20.55 mmol) and 18-crown-6 (1.086 g, 4.11 mmol) were dissolved in dry DMSO (50 ml.) and treated with 20% potassium t- butoxide in THF (1 1.50 g, 20.55 mmol) for 15 minutes at room temperature. 1- bromo-2,5-dichloro-3-fluorobenzene (7.21 g, 29.6 mmol) was added in one portion and the reaction mixture heated at 1 100C for 3 days at which time LC-MS indicated nearly complete consumption of phenol and formation of a major new product. Addition of water to the reaction mixture resulted in a brown gummy oil which was extracted with EtOAc. The organic phase was isolated, washed with brine four times, dried over MgSOphi filtered and concentrated to dryness to give a brown syrup. This material was filtered through a plug of 45 g silica gel which was eluted with 500 ml_ DCM. The filtrate was concentrated to an amber oil and crystallized from EtOH and a few drops of water. This mixture was cooled in an ice bath, filtered, and the precipitate washed with three portions of cold EtOH to give 2-[(3-bromo-2,5- dichlorophenyl)oxy]-1-chloro-3-fluoro-4-methylbenzene (4.0 g, 10.40 mmol, 50.6 % yield) as a cream solid. 1 H NMR (400 MHz, DMSO-c/6) delta ppm 7.73 (s, 1 H), 7.29 – 7.47 (m, 2 H), 6.81 (s, 1 H), 2.29 (s, 3 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; SMITHKLINE BEECHAM CORPORATION; WO2008/154271; (2008); A1;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

Electric Literature of 127049-87-0, The chemical industry reduces the impact on the environment during synthesis 127049-87-0, name is 1-Bromo-2,4-dichloro-3-methylbenzene, I believe this compound will play a more active role in future production and life.

Treat a mixture of 1-bromo-2,4-dichloro-3-methyl-benzene (76.01 g, 0.316 mol) and N-bromosuccinimide (59.2 g, 0.332 mol) in CCl4 (500 mL) with benzoyl peroxide (0.77 g, 3.18 mmol) and is heat to reflux for 6 hours under N2. Cool the reaction mixture to 0 C. and filter using hexanes to rinse the solids. Extract the filtrate with water and saturated NaHCO3. Dry the organic layer (Na2SO4) and remove the solvent in vacuo to afford 97.89 g (97%) of the titled product. Rf=0.34 (100% hexanes).

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-2,4-dichloro-3-methylbenzene, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; Aicher, Thomas Daniel; Anzeveno, Peter Biagio; Li, Renhua; Krasutsky, Alexei Pavlovych; Mabry, Thomas Edward; Saeed, Ashraf; Snyder, Nancy June; Stephenson, Gregory Alan; Tian, Hongqi; Wallace, Owen Brendan; Winneroski, JR., Leonard Larry; Xu, Yanping; US2009/111800; (2009); 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. 69411-05-8, name is 3-Chloro-5-trifluoromethylaniline, This compound has unique chemical properties. The synthetic route is as follows., name: 3-Chloro-5-trifluoromethylaniline

To a mixture of 3-chloro-5-(trifluoromethyl)aniline (3.25 g, 16.6 mmol, Eq: 1.00) in dimethylsulfoxide (43.4 ml) was added N-bromosuccinimide (3.11 g, 17.4 mmol, Eq: 1.05) in 5 portions over 2.5 hr (622 mg each 30 min). 2h after the last addition, the reaction mixture was partitioned between 10% aqueous sodium sulfite and ethyl acetate. The organic layer was washed with aqueous sat. sodium carbonate, water (3 times) and brine then adsorbed unto silica (6g) and purified on silica gel (column 120 g, Hexane/ethyl acetate 90: 10 to 65:35) to give 4.36 g (96%) of a yellow solid. MS +m/z: 275.8 (M+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 69411-05-8.

Reference:
Patent; F. HOFFMANN-LA ROCHE AG; HOFFMANN-LA ROCHE INC.; PLANCHER, Jean-Marc; WEIKERT, Robert James; WO2014/135423; (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. 6626-57-9, name is 1,3-Dichloro-2,2-dimethoxypropane, A new synthetic method of this compound is introduced below., Product Details of 6626-57-9

The last step was dissolved in 125mL solid 42.24g methylene chloride: water = 6: 1 in a mixed solvent, at 20-35 under fed 42.0g chlorine, chlorine was stopped and stirring was continued for 0.5 hours, after standing points the aqueous layer, the organic layer was dried over anhydrous magnesium sulfate, and the solvent evaporated under reduced pressure and the low-boiling by-products, 1,3-dichloro-acetone to give a colorless liquid 30.45 g, 97.7% pure by gas chromatography, a yield of 96.2%

The synthetic route of 6626-57-9 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Southeast University; Wang, MingLiang; Wang, Jia; Dan, hongbin; Gu, xiantao; Wang, shengzhi; Zhang, Wei; (5 pag.)CN105461529; (2016); A;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

Synthetic Route of 69411-05-8, A common heterocyclic compound, 69411-05-8, name is 3-Chloro-5-trifluoromethylaniline, molecular formula is C7H5ClF3N, 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: To a solution of 3-chloroaniline 5a (37mg, 0.33mmol) in H2O (10mL cooled to-5C) was added 0.2mL of 2N HCl (aq.). To the resulting acidic aniline solution, 1N solution of sodium nitrite (0.33mL, 0.33mmol) was added dropwise to generate the aryldiazonium salt solution 6a. To the aryldiazonium salt solution was added sodium acetate (54mg, 0.66mmol), followed by 1mL solution of crude 3-oxo-3-(3-phenylisoxazol-5-yl)propanenitrile 4a (88mg, 0.33mmol) in ethanol. The reaction mixture was stirred at 0C for 5min, and then poured onto H2O (10mL) and extracted with ethyl acetate (20mL). The organic layer was dried over Na2SO4, filtered and concentrated under reduced pressure. The residue was purified by short column chromatography on silica gel, eluting with hexane/ethyl acetate (2/1) to provide the desired product 7 (67mg, 50% for two steps from 3a) as a yellow solid.

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; Ye, Na; Zhu, Yingmin; Liu, Zhiqing; Mei, Fang C.; Chen, Haiying; Wang, Pingyuan; Cheng, Xiaodong; Zhou, Jia; European Journal of Medicinal Chemistry; vol. 134; (2017); p. 62 – 71;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

Synthetic Route of 120758-03-4,Some common heterocyclic compound, 120758-03-4, name is 2-Chloro-3,5-dimethoxyaniline, molecular formula is C8H10ClNO2, 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 1-(2,4,6-trifluorophenyl)-1-propanone (7.0 g, 37.2 mmol), 2-chloro-3,5-dimethoxybenzenamine (see European Patent 1333028 for a method of preparation) (6.96 g, 37.1 mmol) and p-toluenesulfonic acid (1.41 g, 8.2 mmol) in toluene (80 mL) was heated at reflux with use of a Dean-Stark trap to remove water. After 20 h, the reaction mixture was cooled to room temperature and diluted with ethyl acetate. The organic layer was washed with water, sulfuric acid (1 N), water and saturated aqueous sodium chloride solution. The organic layer was dried (Na2SO4), filtered and concentrated to provide the title compound (10 g) which was used without further purification in Step C below.

The synthetic route of 120758-03-4 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; E.I. DU PONT DE NEMOURS AND COMPANY; US2010/160385; (2010); A1;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

Synthetic Route of 69411-05-8, 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. 69411-05-8, name is 3-Chloro-5-trifluoromethylaniline belongs to chlorides-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below.

General procedure: To a solution of 3-chloroaniline 5a (37mg, 0.33mmol) in H2O (10mL cooled to-5C) was added 0.2mL of 2N HCl (aq.). To the resulting acidic aniline solution, 1N solution of sodium nitrite (0.33mL, 0.33mmol) was added dropwise to generate the aryldiazonium salt solution 6a. To the aryldiazonium salt solution was added sodium acetate (54mg, 0.66mmol), followed by 1mL solution of crude 3-oxo-3-(3-phenylisoxazol-5-yl)propanenitrile 4a (88mg, 0.33mmol) in ethanol. The reaction mixture was stirred at 0C for 5min, and then poured onto H2O (10mL) and extracted with ethyl acetate (20mL). The organic layer was dried over Na2SO4, filtered and concentrated under reduced pressure. The residue was purified by short column chromatography on silica gel, eluting with hexane/ethyl acetate (2/1) to provide the desired product 7 (67mg, 50% for two steps from 3a) as a yellow solid.

The synthetic route of 3-Chloro-5-trifluoromethylaniline has been constantly updated, and we look forward to future research findings.

Reference:
Article; Ye, Na; Zhu, Yingmin; Liu, Zhiqing; Mei, Fang C.; Chen, Haiying; Wang, Pingyuan; Cheng, Xiaodong; Zhou, Jia; European Journal of Medicinal Chemistry; vol. 134; (2017); p. 62 – 71;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics