Author: Jessica.F

Reference 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.

Intermediate 1 3-Chloro-5-(trifluoromethyl)benzenesulfonyl chloride [0115] [0116] A solution of NaNO2 (6.50 g) was added to a suspension of 3-chloro-5-(trifluoromethyl)aniline (18.44 g) in concentrated HCl/acetic acid (83 mL/30 mL) at 0 C. and the mixture stirred for one hour. The diazonium salt formed was transferred into a saturated solution of sulfur dioxide in glacial acetic acid (350 mL) at 0 C. and the mixture was warmed up to room temperature for one hour. The mixture was poured onto ice-water and extracted with diethyl ether. The combined organic layers were washed with sodium hydrogen carbonate, dried over sodium sulphate, concentrated and purified by silica chromatography eluting with ethyl actetate/hexane to yield 3-chloro-5-(trifluoromethyl)benzenesulfonyl chloride (22 g, 84%). [0117] 1H NMR (400 MHz, Chloroform-D) d ppm 8.0 (m, 1H) 8.2 (m, 1H) 8.2 (t, J=1.9 Hz, 1H).

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

Reference:
Patent; CONVERGENCE PHARMACEUTICALS LIMTED; Gleave, Robert James; Hachisu, Shuji; Page, Lee William; US2013/116270; (2013); A1;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

Application of 3260-88-6, 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. 3260-88-6 name is 2-Methyl-3-chloroanisole, 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.

2-Chloro-6-methoxytoluene (5 g, 32 mmol) was dissolved in benzene (100 ml) and N-bromosuccinimide (6.8 g, 38 mmol) and perbenzoic acid (5 mg) were added. The mixture was stirred overnight at 80 C. A treatment according to a conventional method using ethyl acetate as an extraction solvent gave a crude product. The obtained crude product was dissolved in dimethyl sulfoxide (100 ml), sodium cyanide (1.86 g, 38 mmol) was added, and the mixture was stirred overnight at room temperature. A treatment according to a conventional method using ethyl acetate as an extraction solvent gave a crude product, which was successively purified by silica gel column chromatography to give a nitrile intermediate (4.3 g, 23.8 mmol)

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

Reference:
Patent; Yamada, Tatsuhiro; Nakagawa, Tadakiyo; Tanaka, Yasuhiro; Fujita, Kohichi; Tagami, Tomoyuki; Ikenoue, Yuka; Fukuda, Shunsuke; Chujo, Yoshitomo; Suzuki, Manabu; Murata, Masahiro; US2005/250796; (2005); A1;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

2770-01-6, name is 4-Chloro-1H-imidazo[4,5-c]pyridine, 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

A mixture of 200 mg (1.3 mmol) of 4-chloro-lH-imidazo[4,5-c]pyridine [J. A.Montgomery and K. Hewson, J. Med. Chern., 8, 708 (1965)], 0.253 mL (261 mg, 5.2 mmol) of hydrazinehydrate, and 5 mL of ethanol was stirred at room temperature overnight. The precipitate was collectedon a filter, washed with a little ethanol, and dried to give the title compound as a solid. LC-MS 150(M+l).

The synthetic route of 2770-01-6 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; MERCK & CO., INC.; WO2006/23750; (2006); A2;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

Adding a certain compound to certain chemical reactions, such as: 60811-17-8, name is 5-Bromo-2-chloroaniline, 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 60811-17-8, Safety of 5-Bromo-2-chloroaniline

5-Bromo-2-chloro-phenylamine (0.48 g) is dissolved in pyridine (6 mL) and the solution is cooled to O0C. Benzenesulfonyl chloride (0.41 g) in DCM (2 mL) is added dropwise. The solution is stirred at O0C for 30 minutes and at room temperature for 2 hours. Pyridine is removed under reduced pressure and the residue is dissolved in EtOAc. The organic layer is washed with 10% aqueous HCl, saturated NaHCO3, and brine. The organic layer is dried (MgSO4), filtered and evaporated and the crude material is recrystallized from EtO Ac/heptane to afford N-(‘5-bromo-2-chloro-phenyl’)- benzenesulfonamide (O.62 g) as a solid. LCMS: Rtau = 3.06 minutes, MS: 346 (M+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, 5-Bromo-2-chloroaniline, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; AVENTIS PHARMACEUTICALS INC.; WO2006/81343; (2006); A1;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

29682-44-8, name is 1-Bromo-2,4,5-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. COA of Formula: C6H2BrCl3

To a sealed tube were added l -bromo-2,4,5-trichlorobenzene (3.0 g, 12 mmol), 1,2-dimethoxyethane: water ( 10 : 1 , 30 mL), (f)-2-(4-methoxystyryl)-4,4,5,5- tetramethyl- l,3,2-dioxaborolane (C6 4) (3.7 g, 14 mmol ), and potassium carbonate (3.2 g, 24 mmol) . The reaction mixture was degassed for 10 minutes with argon, followed by addition of tetrakis(triphenylphosphine)palladium(0) (0.55 g, 0.48 mmol) . The reaction mixture was degassed for 10 minutes then heated at 90 C for 16 hours. The reaction mixture was poured in to water and extracted with ethyl acetate. The combined organic layers were dried over sodium sulfate, filtered, and concentrated . Purification by flash column chromatography provided the title compound as an off-white solid (3.0 g, 80%) : NM R (400 MHz, CDC ) delta 7.73 (s, 1H), 7.50 – 7.45 (m, 3H), 7.20 (d, J = 16.0 Hz, 1 H), 7.02 (d, J = 16 Hz, 1H), 6.92 (d, J = 8.0 Hz, 2H), 3.84 (m, 3H) ; ESIMS m/z 313 ( [Mu + EtaGamma).

The synthetic route of 29682-44-8 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; DOW AGROSCIENCES LLC; HEEMSTRA, Ronald J.; ROSS, Ronald; DEKORVER, Kyle A.; GRAY, Kaitlyn; KNUEPPEL, Daniel I.; VEDNOR, Peter; MARTIN, Timothy P.; ECKELBARGER, Joseph D.; DAEUBLE, John F.; HUNTER, Ricky; DEMETER, David A.; TRULLINGER, Tony K.; BAUM, Erich W.; BENKO, Zoltan L.; CHOY, Nakyen; CROUSE, Gary D.; LI, Fangzheng; NISSEN, Jeffrey; OLSON, Monica B.; RIENER, Michelle; SPARKS, Thomas C.; WESSELS, Frank J.; YAP, Maurice C.; (981 pag.)WO2016/168059; (2016); A1;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

Adding a certain compound to certain chemical reactions, such as: 179897-90-6, name is 1,3-Dibromo-2-chloro-5-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 179897-90-6, Safety of 1,3-Dibromo-2-chloro-5-fluorobenzene

l,3-Dibromo-2-chloro-5-fluorobenzene (400 mg, 1.39 mmol) dissolved in toluene (4 mL) and 2- methyltetrahydrofuran (1 mL) was treated with the triisopropyl borate (390 pL, 1.69 mmol). The mixture was cooled to -78 C in a dry ice/acetone bath and then n-butyllithium (2.5 M in hexanes, 680 pL, 1.70 mmol) was added slowly dropwise. The mixture was maintained at -78 C for 1 h and then slowly allowed to warm to room temperature. After stirring for 1 h, the reaction mixture was quenched by adding 1N HC1 solution, diluted with ethyl acetate and washed with water and brine. The organic layer was dried over sodium sulfate and filtered. The filtrate was concentrated and purified by ISCO silica gel chromatography to give (3-bromo-2-chloro-5-fluorophenyl)boronic acid.

At the same time, in my other blogs, there are other synthetic methods of this type of compound, 1,3-Dibromo-2-chloro-5-fluorobenzene, and friends who are interested can also refer to it.

Reference:
Patent; GILEAD SCIENCES, INC.; AKTOUDIANAKIS, Evangelos; CHO, Aesop; DU, Zhimin; GRAUPE, Michael; LAD, Lateshkumar Thakorlal; MACHICAO TELLO, Paulo A.; MEDLEY, Jonathan William; METOBO, Samuel E.; MUKHERJEE, Prasenjit Kumar; NADUTHAMBI, Devan; PARKHILL, Eric Q.; PHILLIPS, Barton W.; SIMONOVICH, Scott Preston; SQUIRES, Neil H.; WANG, Peiyuan; WATKINS, William J.; XU, Jie; YANG, Kin Shing; ZIEBENHAUS, Christopher Allen; (300 pag.)WO2019/204609; (2019); A1;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

Application of 54773-20-5, A common heterocyclic compound, 54773-20-5, name is 1,3-Dichloro-5-(trifluoromethyl)benzene, molecular formula is C7H3Cl2F3, 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.

STEP A: 2,6-dichloro-4-(trifluoromethyl)benzaldehyde A 2M n-BuLi solution (5.8 mL, 11.6 mmol) was added to a -78 C. THF solution (60 mL) of 1,3-dichloro-5-(trifluoromethyl)benzene (2.5 g, 11.6 mmol). After 45 min neat DMF (0.39 mL, 5.0 mmol) was added, and the resulting solution was allowed to warm to 0 C. gradually, quenched with NH4Cl solution, and extracted with diethyl ether. The combined extracts were dried (Na2SO4), concentrated, and purified via column chromatography to yield the title compound.

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; Chakravarty, Devraj; Greco, Michael; Shook, Brian; Xu, Guozhang; Zhang, Rui; US2012/302641; (2012); 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 59772-49-5 as follows. HPLC of Formula: C6H5BrClN

Benzofuran-3-ylboronic acid2-bromo-6-chloroaniline (189 g, 1100 mmol) was dissolved in toluene (Toluene), EtOH, H2O (400 mg, 400 mL). Pd (PPh3) 4 (58 g, 50 mmol) and NaHCO3 (252 g, 3000 mmol) were added thereto and refluxed for 4 hours. After completion of reaction, MC is extracted by cooling to room temperature. After drying over anhydrous MgSO4, the solvent is removed by rotary evaporator. Column chromatography (MC: Hx = 1: 3) was used to obtain the desired compound 461-5. (190 g, 91percent, brown oil)

According to the analysis of related databases, 59772-49-5, the application of this compound in the production field has become more and more popular.

Reference:
Patent; L Ti Material Co., Ltd.; Oh Han-guk; Lee Yun-ji; Ji Hye-su; Jeong Won-jang; Choi Jin-seok; Choi Dae-hyeok; (212 pag.)KR2019/33885; (2019); A;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

Adding a certain compound to certain chemical reactions, such as: 129482-45-7, name is 4-Benzyl-2-(chloromethyl)homomorpholine, 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 129482-45-7, name: 4-Benzyl-2-(chloromethyl)homomorpholine

EXAMPLE 54 (4-Benzyl-1,4-oxazepan-2-ylmethyl)-phenyl amine 80 Aniline (2.59 mL, 28.4 mmol) and NaI (4.06 g, 27.1 mmol) were added to a solution of 4-benzyl-2-chloromethyl-1,4-oxazepane (79) (6.49 g, 27.1 mmol) in n-butanol (68 mL, 0.4 M), and the reaction was heated to 110 C. until the reaction was judged complete by TLC (4 h). The reaction was cooled to room temperature, and water and CH2Cl2 were added. The organic layer was removed, and the aqueous layer was extracted with CH2Cl2 (2*). The combined organic extracts were dried over sodium sulfate, filtered and concentrated in vacuo to achieve (4-benzyl-1,4-oxazepan-2-ylmethyl)-phenyl amine 80, which was used without purification in the next reaction. 1H NMR (partial, CDCl3) 4.08-3.86 (3H, m), 3.80 (1H, d, J=13.3 Hz), 3.73 (1H, d, J =13.3 Hz), 3.22-3.05 (2H,.m), 2.95-2.70 (3H, m), 2.64 (1H, dd, J=13.6, 7.6 Hz), 2.1-1.9 (2H, m) ppm. 13C NMR (CDCl3) 148.33, 139.38, 129.28, 129.11, 128.46, 127.23, 117.44, 113.13, 76.70, 67.49, 62.92, 59.35, 54.76, 46.93, 30.75 ppm. LRMS: 296.68.

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; Cuny, Gregory D.; Shao, Liming; Hauske, James R.; Heffernan, Michele L.R.; Aquila, Brian M.; Wu, Xinhe; Wang, Fengjiang; Bannister, Thomas D.; US2002/16337; (2002); 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. 120758-03-4, name is 2-Chloro-3,5-dimethoxyaniline, A new synthetic method of this compound is introduced below., Application In Synthesis of 2-Chloro-3,5-dimethoxyaniline

Step 4 14.4 g of potassium isocyanate were dissolved at 10ØC in 450 ml of’acetone. 14.2 ml of benzoylchloride were added dropwise carefully. The white suspension was refluxed 10 minutes and then cooled again to 10ØC. A solution of 28 g of 2-chloro-3,5-dimethoxyaniline in 300 m! of acetone was then added and the obtained mixture refluxed over 3 h. 700 ml of water with ice were added and the aqueous phase was extracted with 3×600 ml of ethyl acetate. The organic phase was then dried over magnesium sulfate and concentrated. The brown residue was dissolved in 100 ml ethanol and refluxed together with 35 ml of an aqueous solution of potassium hydroxide. After 1 hour, 500 ml of water were added. Ethanol was distilled under reduced pressure. The brown solution was neutralized with 300 ml of an ammonium chloride solution and the solid which precipitated was filtered, washed with water and dried. 35 g of (2-chloro-3,5-dimethoxy-phenyl)-thiourea were obtained as a brown powder, m.p. 159-162ØC

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; Boehringer Ingelheim Pharma GmbH & Co.KG; EP1333028; (2003); A1;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics