Month: March 2021

Reference of 2729-34-2,Some common heterocyclic compound, 2729-34-2, name is 3,5-Dichloro-4-fluoroaniline, molecular formula is C6H4Cl2FN, 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.

3,5-dichloro-4-fluoroaniline (1.0 g, 5.59 mmol) was dissolved in 10 ml HCl at 0C, NaN02 (386 mg, 5.59mmol) dissolved in water was added slowly and the solution was stirred at 0C until the solution was clear. The reaction mixture was slowly added a stirred solution of Potassium ethyl xantogenate (1.34 g, 8.38 mmol) in 15 ml water at 50C. The reaction mixture was stirred at 70C for 2 h followed by extraction with EtOAc (100 mL). The organic phase was washed by brine, dried over Na2S04, filtered and concentrated to give 1 g crude product which was immediately used in the next step.

The synthetic route of 2729-34-2 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; GALECTO BIOTECH AB; ZETTERBERG, Fredrik; LEFFLER, Hakon; NILSSON, Ulf; (131 pag.)WO2018/11093; (2018); A1;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

Reference of 50638-46-5, 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. 50638-46-5, name is 4-Bromo-3-chloroanisole belongs to chlorides-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below.

Under an argon atmosphere, 1-bromo-2-chloro-4-methoxybenzene (44.3 g) was dissolved in toluene (220 ml), ethyl 2-(4,4,5,5-tetramethyl[1,3,2]dioxaborolan-2-yl)benzoate (60.8 g), water (132 ml), sodium hydrogen carbonate (33.6 g) and dichlorobis(triphenylphosphine)palladium(II) (2.8 g) were added, and the mixture was stirred at an oil bath temperature of 120 C. for 7 hr. To the reaction mixture was added ethyl 2-(4,4,5,5-tetramethyl[1,3,2]dioxaborolan-2-yl)benzoate (5.2 g), and the mixture was further stirred for 2 hr. The reaction mixture was cooled to room temperature, toluene (100 ml) and water (200 ml) were added, and the mixture was stirred overnight. To the reaction mixture was added activated carbon (3 g), and the mixture was further stirred for 1 hr. The insoluble material was filtered off through Celite, and the insoluble material was washed with toluene (100 ml) and water (200 ml). The obtained filtrates were combined to allow for layer separation. The obtained organic layer was washed with water (100 ml), and the solvent was evaporated to give the title compound (67.7 g). 1H-NMR (400 MHz, DMSO-D6) delta: 7.88-7.86 (1H, m), 7.63 (1H, td, J=7.6, 1.4 Hz), 7.51 (1H, td, J=7.6, 1.4 Hz), 7.27 (1H, dd, J=7.6, 0.9 Hz), 7.18 (1H, d, J=8.6 Hz), 7.06 (1H, d, J=2.6 Hz), 6.95 (1H, dd, J=8.6, 2.6 Hz), 4.01 (2H, m), 3.80 (3H, s), 0.96 (3H, t, J=7.1 Hz).

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

Reference:
Patent; MOTOMURA, Takahisa; MATSUO, Takuya; SHOMI, Gakujun; US2015/18403; (2015); A1;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

Adding a certain compound to certain chemical reactions, such as: 2106-04-9, name is 3-Chloro-2-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 2106-04-9, Product Details of 2106-04-9

To a stirred solution of A1C13 (10.0 g, 75.01 mmol) and BC13 (1Mm n-hexane, 74 mL,75.01 mmol) in CH2C12 (80 mL) was added 3-chloro-2-fluoroaniline 1 (9.0 g, 6.18 mmol) followed by a solution of chloroacetonitrile (11.6 g, 153.64 mmol) in CH2C12 (20 mL) at 0 C under inert atmosphere. The reaction mixture was allowed to stir at RT for 30 minutes and heated to reflux for additional 14 h. The reaction mixture was then cooled to 0 C, added aqueous 3 N HC1 (100 mL) and raised the temperature to reflux and stirred for 3 h. The mixture was cooled RT, diluted with water (50 mL) and extracted with CH2C12 (2 x 150 mL). The combined organic extracts were dried over Na2SO4, filtered and concentrated under reduced pressure to obtain the crude. The crude was purified by triturating with n-pentane to afford compound 2 (4.5 g, 33%) as an off-white solid. 1H NMR (500 MHz, DMSO-d6): (57.61 (d, J= 9.0 Hz, 1H), 7.35 (br s, 2H), 6.72 (d, J 9.0 Hz, 1H), 5.06 (s, 2H).

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

Reference:
Patent; PHARMAKEA, INC.; HUTCHINSON, John, Howard; LONERGAN, David; HUANG, Fei; ROWBOTTOM, Martin; CALDERON, Imelda; WO2015/48301; (2015); A1;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

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 7006-52-2 as follows. Application In Synthesis of N-Methyl-3-chloroaniline

28.2 mg (0.2 mmol) of N-methyl-3-chloroaniline, 81.2 mg of ethyl bromodifluoroacetate (0.4 mmol), 2.5 mg (0.02 mmol) of cuprous acetate, 19.1 mg (0.04 mmol) of X-phos, 32.7 mg (0.2 mmol) of cesium carbonate were added to 2 mL of DMF solvent. The reaction was carried out at 110 C for 12 hours, after the reaction was completed, it was cooled, filtered, and the filtrate was evaporated. The solvent was removed and the residue was chromatographed on silica gel. It was washed with a mixed solution of petroleum ether and ethyl acetate in a volume ratio of 8:1. The effluent was collected according to the actual gradient, detected by TLC, and the effluent containing the product was combined. The solvent was distilled off by a rotary evaporator. Drying in vacuo to give the yellow liquid N-methyl-N-(3-chlorophenyl)carboxamide 23.0 mg, yield 68%.

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:
Patent; Wenzhou University; Zhang Xiaohong; Li Xiaofang; Zhang Xingguo; (15 pag.)CN108774147; (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. 41965-95-1, name is 3-Chloro-4-methoxybenzylamine Hydrochloride, A new synthetic method of this compound is introduced below., Recommanded Product: 41965-95-1

2-acetyl-10-[(3-chloro-4-methoxybenzyl)amino]-1,2,3,4-tetrahydrobenzo[b][1,6]naphthyridine-8-carbonitrile, H A mixture of 26 (0.14 mmol), 3-chloro-4-methoxybenzyl amine hydrochloride (0.70 mmol), TEA (0.70 mmol) and NaI (0.007 mmol) in NMP (2 mL) was heated to 130 C. and stirred overnight. The mixture was diluted with CH2Cl2 (10 mL) and washed with H2O (2*10 mL) and brine (10 mL). The organic layers were dried over Na2SO4, filtered and evaporated under reduced pressure. Flash Chromatography (AcOEt:MeOH 9:1) gave the desired product (20% yield). MS ESI (m/z) 421 (M+H)+; 1H NMR (300 MHz, CDCl3) delta 8.34 (s, 1H), 7.96 (d, 1H, J=8.7 Hz), 7.73 (dd, 1H, J1=1.5, J2=9.0 Hz), 7.31 (d, 1H, J=2.1 Hz), 7.20 (dd, 1H, J1=2.1, J2=8.4 Hz), 6.93 (d, 1H, J=8.1 Hz), 4.70 (s, 2H), 4.64 (d, 2H, J=6.0 Hz), 4.42 (s, 1H), 3.91 (s, 3H), 3.82 (t, 2H, J=6.0 Hz), 3.20 (t, 2H, J=6.0 Hz), 2.21 (s, 3H).

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; THE TRUSTEES OF COLUMBIA UNIVERSITY IN THE CITY OF NEW YORK; Landry, Donald W.; Deng, Shixian; Arancio, Ottavio; Fiorito, Jole; Wasmuth, Andrew; (41 pag.)US10626113; (2020); B2;,
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. 367-22-6, name is 4-Chloro-3-fluoroaniline, This compound has unique chemical properties. The synthetic route is as follows., COA of Formula: C6H5ClFN

Step 1 : tert-butyl (4-chloro-3-fluorophenyl)carbamate. To a solution of 4-chloro-3-fluoroaniline (7.50 g, 51.50 mmol) in DCM (150 mL) was added di-tert-butyl dicarbonate (11.96 mL, 51.5 mmol) dropwise. The reaction mixture was stirred at 25C for 16 h under N2 atmosphere (balloon). TLC showed a new spot and the SM was consumed. The mixture was diluted with water (200 mL) and extracted with EtOAc (150 mL x2). The combined organic layers were dried over Na2S04, filtered and the filtrate was concentrated. The residue was purified by flash silica gel chromatography (0-18% EtOAc/PE gradient) to afford the title compound.

According to the analysis of related databases, 367-22-6, the application of this compound in the production field has become more and more popular.

Reference:
Patent; MERCK SHARP & DOHME CORP.; MERTZ, Eric; EDMONDSON, Scott, D.; SO, Sung-Sau; SUN, Wanying; LIU, Weiguo; NEELAMKAVIL, Santhosh, F.; GAO, Ying-Duo; HRUZA, Alan; ZANG, Yi; ALI, Amjad; MAL, Rudrajit; HE, Jiafang; KUANG, Rongze; WU, Heping; OGAWA, Anthony, K.; NOLTING, Andrew, F.; (152 pag.)WO2016/168098; (2016); A1;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

Adding a certain compound to certain chemical reactions, such as: 13334-71-9, name is 4-Chloro-3-methylanisole, 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 13334-71-9, category: chlorides-buliding-blocks

To a solution of the l-chloro-4-methoxy-2-methylbenzene (2.0 g, 12.77 mmol) in anhydrous carbon tetrachloride (50 mL), NBS (2.29 g, 12.98 mmol) and benzoyl peroxide (0.154 g, 0.64 mmol) was added. The reaction mixture was heated to reflux overnight. Then, the reaction mixture was cooled to room temperature and filtered. The filtrate was evaporated to provide crude 2-(bromomethyl)-l-chloro-4- methoxybenzene, which was used for the next step without any further purification; 1H NMR (400 MHz, DMSO-J6): delta 3.74 (s, 3H), 4.66 (s, 2H), 7.01 (d, J = 8.9 Hz, IH), 7.19 (s, IH), 7.38 (d, J = 8.9 Hz, IH).

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:
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

Application of 433-94-3, The chemical industry reduces the impact on the environment during synthesis 433-94-3, name is 2-Chloro-6-(trifluoromethyl)aniline, I believe this compound will play a more active role in future production and life.

The reaction flask was charged with 2-chloro-6-trifluoromethylaniline (460 mg, 2.36 mmol)Sodium hydride (130 mg,60%, 3.25 mmol) and 10 ml of tetrahydrofuran,Stirring at room temperature was added dropwise 4-difluoromethyl-1,2,3-thiadiazole-5-carboxylic acid chloride (470 mg, 2.36 mmol) in 10 ml tetrahydrofuran.Drop finished, reaction at room temperature,2 hours after the reaction is completed.The reaction solution was poured into 30 ml of water,Take the organic layer,The organic layer was washed successively with saturated aqueous sodium bicarbonate,Saturated brine washing,Dried over anhydrous magnesium sulfate,Heat the solvent under reduced pressure.The residue was purified by column chromatography (eluent: ethyl acetate: petroleum ether = 1: 8)To give 190 mg of compound 79 in 23% yield.

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, 2-Chloro-6-(trifluoromethyl)aniline, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; Shenyang Sinochem Pesticide Chemical Research And Development Co., Ltd.; Lv Liang; Wang Gang; Li Keke; Zhang Wen; Liu Shaowu; Liang Shuang; Wu Shasha; Li Bin; (17 pag.)CN106831647; (2017); A;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

Reference of 6120-31-6, 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. 6120-31-6, name is 5,6-Dichlorobenzo[d][1,3]dioxole belongs to chlorides-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below.

ft-BuLi (2.5 M, 500 uL) was added drop wise to a mixture of 5,6-dichloro- 1,3- benzodioxole (200 mg, 1.1 mmol) in THF (5 mL) at -78 C. After 30 min, B(OMe)3 (163 mg, 1.6 mmol) was added at -78 C. The reaction was allowed to warm to 20 C for over 2 hr and IN HCl was added. After extraction with EtOAc the combined organic layers were washed with brine, dried over Na2S04, filtered and concentrated under reduced pressure to give (5,6-dichloro- l,3-benzodioxol-4-yl)boronic acid (200 mg, 684 umol, 80% purity) as a light yellow solid. (1078) LCMS (ESI): m/z: [M -H] calculated for C7H4BCI2C : 232.9; found 233.0.

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, 5,6-Dichlorobenzo[d][1,3]dioxole, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; REVOLUTION MEDICINES, INC.; LI, Jie Jack; KOLTUN, Elena S.; GILL, Adrian Liam; BUCKL, Andreas; WON, Walter; AAY, Naing; MELLEM, Kevin; TZITZILONIS, Christos; JOGALEKAR, Ashutosh; CREGG, James Joseph; (177 pag.)WO2019/75265; (2019); A1;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

108-70-3, name is 1,3,5-Trichlorobenzene, 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. Application In Synthesis of 1,3,5-Trichlorobenzene

Synthesis Example 5 Synthesis of 1,3,5-Trichloro-2,4,6-tris(phenylethynyl)benzene (corresponding to Scheme 3-(8)) [Show Image] Under a nitrogen atmosphere, in a 100 mL three-neck flask, 1,3,5-trichloro-2,4,6-triiodobenzene (5.0 g, 8.94 mmol) obtained in Synthesis Example 1, diisopropylamine (4.5 mL) and THF (40 mL) were placed and degassed by Ar bubbling for 30 minutes. Pd(PPh3)4 (200 mg, 0.17 mmol), CuI (310 mg, 1.6 mmol) and ethynyl benzene (3.92 mL, 35.8 mmol) were added and refluxed for 20 hours. After the reaction was terminated with a 1N hydrochloric acid solution (20 mL), the reaction mixture was extracted with methylene chloride (50 mL x 3), washed with an aqueous sodium hydrogen carbonate solution (150 mL x 1) and saturated saline solution (150 mL x 2) and dried over anhydrous magnesium sulfate. After the solvent was distilled away under reduced pressure, a by-product(s) was removed by column chromatography (silica gel, hexane, butch) and purification was performed by column chromatography (silica gel, hexane: methylene chloride = 10:1, Rf = 0.38). The resultant solid substance was dissolved in hot benzene and reprecipitated from hexane to obtain a white solid substance (3.3 g, 77%). 1H-NMR(400MHz,CDCl3)delta7.64-7.60(m,6H), 7.42-7.35(m,9H); 13C-NMR(99.5MHz,CDCl3)delta138.1,132.1, 129.5, 128.6, 123.1., 122.4, 101.1, 83.3; M.S.(70eV,EI)m/z=482(M+); mp186.8-187.3C

The synthetic route of 108-70-3 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Hiroshima University; Nippon Kayaku Kabushiki Kaisha; EP2361915; (2011); A1;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics