Author: Jessica.F

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. 33863-76-2, name is 1-Bromo-3-chloro-5-fluorobenzene, A new synthetic method of this compound is introduced below., category: chlorides-buliding-blocks

4-Trifluoromethyl-6-(3-fluoro-5-chloro)phenyl-2(1H)-quinolinone (Compound 732, Structure 145 of Scheme XXX, Where R=H, R1=Trifluoromethyl, R2=3-Fluoro-5-chloro) 3-Chloro-5-fluorobenzeneboronic Acid (Compound 733, Structure 144 of Scheme XXX, Where R2=3-Fluoro-5-chloro): This compound was prepared according to General Procedure XXIII in Example 406 from 1-bromo-3-chloro-5-fluorobenzene (20 g, 0.18 mmol), n-BuLi (8.2 M in hexane, 21 mL, 0.18 mmol), and trimethyl borate (60 mL, 0.53 mmol) to give 2,3-difluoro-benzeneboronic acid as a white 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:
Patent; Ligand Pharmaceuticals Incorporated; US6566372; (2003); B1;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

Application of 1871-57-4, These common heterocyclic compound, 1871-57-4, name is 3-Chloro-2-chloromethyl-1-propene, 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.

To a solution of Compound 1 (1.32 g, 10.5 mmol) in DMF (20 mL) was added NaH (960 mg, 24 mmol) at 0 C., the mixture was stirred at 0 C. for 30 min. Then compound 2 (1.61 g, 10 mmol) was added at 0 C. The mixture was stirred at 15 C. for 2 hours. TLC showed that starting material was consumed completely. Saturated NH4Cl (100 mL) was added to quench the reaction. The solvent was removed in vacuo and the residue was extracted with EA (100 mL*2). The organic layer was concentrated and purified by silica gel column (PE:EA=4:1) to give compound 3 (1.1 g, yield: 51%) as colorless oil. 1H NMR (400 MHz, CDCl3): delta: 5.12-4.91 (m, 2H), 4.29-4.03 (m, 4H), 3.76-3.45 (m, 4H), 1.47 (s, 9H).

Statistics shows that 3-Chloro-2-chloromethyl-1-propene is playing an increasingly important role. we look forward to future research findings about 1871-57-4.

Reference:
Patent; Novira Therapeutics, Inc.; Hartman, George D.; US2015/225355; (2015); 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. 4152-90-3, name is (3-Chlorophenyl)methanamine, A new synthetic method of this compound is introduced below., SDS of cas: 4152-90-3

A solution of 5-chloro-jV-cyclohexylpyrazolo[ 1 ,5-alpha]pyrimidine-3-carboxamide(28 mg, 0.09 rnM, 1.0 equiv), 3-chlorobenzylamine (28 mg, 0.18 rnM, 2.0 equiv), N5N- diisopropylethylamine (26 mg, 0.18 rnM, 2.0 equiv) and 2 rnL of ethanol were microwaved at 120 0C for 10 minutes. TLC (95:5 dichloromethane methanol) showed reaction complete. The reaction mixture was cooled, the crystalline product collected by filtration, washed with cold ethanol and air dried to yield 29.7 mg (77percent) of 5-(3-chlorobenzylamino)-7V- cyclohexylpyrazolo[l,5-alpha]pyrimidine-3-carboxamide. LCMS (ESI) m+H = 384.2; 1H NMR (400 MHz, OMSO-d) delta: 8.61 (overlapping d and t, 2 H), 8.06 (s, 1 H), 7.60 (d, 1 H), 7.4- 7.25 (m, 4 H), 6.49 (d, 1 H), 3.70 (m, 1 H), 1.75-1.5 (m, 5 H), 1.4-0.8 (m, 5 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; GENENTECH, INC.; BLANEY, Jeffrey; GIBBONS, Paul A.; HANAN, Emily; LYSSIKATOS, Joseph P.; MAGNUSON, Steven R.; PASTOR, Richard; RAWSON, Thomas E.; ZHOU, Aihe; ZHU, Bing-Yan; WO2010/51549; (2010); A1;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

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