Author: Jessica.F

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,
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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

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 16793-91-2 as follows. Product Details of 16793-91-2

Example 8A Di-tert-butyl (2-{5-[2-(2-chlorophenyl)ethoxy]-1-benzofur-2-yl}-2-oxoethyl)[2-(4-oxo-1,2,3-benzotriazin-3(4H)-yl)ethyl]malonate To a mixture of 100 mg (0.18 mmol) of the compound from Example 7A in 2.5 ml of acetonitrile were added 47 mg (0.21 mmol) of 1-(2-bromoethyl)-2-chlorobenzene and 49 mg (0.36 mmol) of potassium carbonate and the mixture was stirred under reflux for 1.5 h. Then, a further 47 mg (0.21 mmol) of 1-(2-bromoethyl)-2-chlorobenzene and 49 mg (0.36 mmol) of potassium carbonate were added and the mixture was stirred under reflux for a further 4.5 h. Then, the mixture was left to stand firstly overnight at RT and then, after another addition of 47 mg (0.21 mmol) of 1-(2-bromoethyl)-2-chlorobenzene, stirred for a further 5 h at 50 C. After cooling to RT, the mixture was admixed with 1 ml of water and purified directly by preparative HPLC (Method 7). The combined product-containing fractions were neutralized with saturated aqueous sodium hydrogencarbonate solution, concentrated to a residual volume of aqueous phase and extracted twice with dichloromethane. The combined organic phases were dried over magnesium sulphate and concentrated, and the residue was dried in vacuo. 21 mg (17% of theory, purity 100%) of the title compound were obtained. LC/MS (Method 1, ESIpos): Rt=1.59 min, m/z=702 [M+H]+.

According to the analysis of related databases, 16793-91-2, the application of this compound in the production field has become more and more popular.

Reference:
Patent; BAYER PHARMA AKTIENGESELLSCHAFT; BECK, Hartmut; LI, Volkhart Min-Jian; CANCHO GRANDE, Yolanda; TIMMERMAN, Andreas; BROHM, Dirk; JOeRIssEN, Hannah; BOGNER, Pamela; GERISCH, Michael; LANG, Dieter; (120 pag.)US2017/121315; (2017); A1;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

Application of 2533-69-9,Some common heterocyclic compound, 2533-69-9, name is Methyl 2,2,2-trichloroacetimidate, molecular formula is C3H4Cl3NO, 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) A solution of N-(4-methoxybutyl)-o-phenylenediamine in toluene was cooled to 0-10 C., and acetic acid (65.2 g, 1.09 mol) and methyl 2,2,2-trichloroacetimidate (70.3 g, 0.398 mol) were added. After stirring at 0-10 C. for 30 min, the mixture was stirred at 20-30 C. for 3 hr. The reaction mixture was successively washed with 5 w/v % brine (250 mL), a mixed solution of 2N hydrochloric acid/5 w/v % brine (1:1, 250 mL*2), 5 w/v % sodium bicarbonate water (250 mL) and 5 w/v % brine (250 mL). Under a nitrogen stream, magnesium sulfate (25.0 g) was added to the organic layer at 20-30 C., and the mixture was stirred at the same temperature for 30 min. Magnesium sulfate was filtered off and the residue was washed with toluene (100 mL). The filtrate was concentrated under reduced pressure to give the content (150 mL). The concentrated solution was stirred at 20-30 C., the crystals were precipitated, and heptane (750 mL) was added dropwise. The crystallized solution was heated to 40-50 C. and stirred for 30 min. After stirring, the solution was cooled to 0-10 C. and stirred at the same temperature for 2 hr. The precipitated crystals were collected by filtration, washed with toluene-heptane (1:5, 150 mL) and dried under reduced pressure at 40 C. to give 1-(4-methoxybutyl)-2-trichloromethyl-1H-benzimidazole as pale brown crystals (96.5 g, yield 82.9% from o-nitroaniline).1H-NMR (300 MHz, CDCl3) delta: 1.68-1.85 (m, 2H), 1.99-2.17 (m, 2H), 3.37 (s, 3H), 3.48 (t, J=6.1 Hz, 2H), 4.50-4.65 (m, 2H), 7.27-7.49 (m, 4H), 7.82-7.93 (m, 1H).[0086]Anal. Calcd for C13H15Cl3N2O: C, 48.55; H, 4.70; N, 8.71; Cl, 33.07. Found: C, 48.30; H, 4.61; N, 8.74; Cl, 33.30.

The synthetic route of 2533-69-9 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Kitayama, Masato; US2013/90337; (2013); 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. Computed Properties of C7H8ClN

To a solution of 4-chloro-l-methyl-lH-pyrrolo[3,2-c]pyridine-7-carboxylic acid methyl ester (0.5g) in 1,4-dioxane (5ml) was added 3-chloro-N-methyl aniline (0.629g) and methanesulfonic acid (0.289ml). The mixture was irradiated under microwave conditions at 180¡ãC for 30min. 1,4-dioxane was removed in vacuo and the residue purified by MDAP to give the title compound (350mg). LC/MS [MH+] 330 consistent with molecular formula C17H1635ClN3O2

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; GLAXO GROUP LIMITED; WO2005/121140; (2005); A1;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

Some common heterocyclic compound, 13726-14-2, name is 4-Chloro-3-methoxyaniline, molecular formula is C7H8ClNO, 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: Compounds 2-19 were synthesized by reductive alkylation ofcommercially available anilines with N-Boc-2-aminoacetaldehydeand benzoylation with 2,4-dichlorobenzoyl chloride with subsequentremoval of Boc-protecting group with 4 N HCl in dioxane.Compound precipitated from hexane/ dioxane reaction mixtureas HCl salt.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 13726-14-2, its application will become more common.

Reference:
Article; Buchynskyy, Andriy; Gillespie, J. Robert; Hulverson, Matthew A.; McQueen, Joshua; Creason, Sharon A.; Ranade, Ranae M.; Duster, Nicole A.; Gelb, Michael H.; Buckner, Frederick S.; Bioorganic and Medicinal Chemistry; vol. 25; 5; (2017); p. 1571 – 1584;,
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. 6775-78-6, name is 6-Chloroimidazo[1,2-b]pyridazine, A new synthetic method of this compound is introduced below., Recommanded Product: 6775-78-6

478 mg (3.11 mmol) of 6-chloroimidazo[l,2-b]pyridazine were introduced into 10 mL of chloroform under argon and, while cooling in ice, 664 mg (3.73 mmol) of /V-bromo- succinimide were added. After the addition was complete, the reaction mixture was stirred at room temperature overnight. The reaction mixture was then mixed with water and ethyl acetate and, after addition of saturated sodium bicarbonate solution, the phases were separated. The aqueous phase was extracted three more times with ethyl acetate. The combined organic phases were then washed with saturated sodium chloride solution and dried over sodium sulfate. In the final removal of the solvent in vacuo, the desired product was isolated in quantitative yield in the form of an amorphous white solid which was employed without further chromatographic purification in subsequent reactions. H-NMR (CHLOROFORM-d): delta [ppm] = 7.12 (d, 1H); 7.79 (s, 1H); 7.90, (d, 1H).

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; BAYER PHARMA AKTIENGESELLSCHAFT; EIS, Knut; PUeHLER, Florian; ZORN, Ludwig; SCHULZE, Volker; SUeLZLE, Detlev; LIENAU, Philip; WENGNER, Antje, Margret; PETERSEN, Kirstin; BOeMER, Ulf; WO2014/128093; (2014); 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. 821-10-3, name is 1,4-Dichlorobut-2-yne, This compound has unique chemical properties. The synthetic route is as follows., Quality Control of 1,4-Dichlorobut-2-yne

General procedure: The [2 + 2 + 2] cycloaddition was performed in a similar manner as described in [3]. In brief, to a solution of diyne (1 equiv) and propargyl halide (2 equiv) in dry acetonitrile (5 mL), Mo(CO)6 (5 mol %) was added and the reaction mixture was stirred under MWI conditions for 10-15 min. After completion of the reaction (TLC), the reaction mixture was concentrated at reduced pressure and the crude product was purified by silica gel column chromatography using EtOAc/petroleum ether 5:95 to 30:70 to give the [2 + 2 + 2] cyclotrimerized compounds.

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 821-10-3.

Reference:
Article; Kotha, Sambasivarao; Sreevani, Gaddamedi; Dzhemileva, Lilya U.; Yunusbaeva, Milyausha M.; Dzhemilev, Usein M.; D?yakonov, Vladimir A.; Beilstein Journal of Organic Chemistry; vol. 15; (2019); p. 2774 – 2781;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

Adding a certain compound to certain chemical reactions, such as: 309721-44-6, name is 2-Bromo-1-chloro-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 309721-44-6, Quality Control of 2-Bromo-1-chloro-3-fluorobenzene

General procedure: To a mixture of intermediate C-3 (1 eq), halo-(hetero)arene BB-16 (1.1 to 2 eq) and sodium ferf-butoxide (2 to 2.3 eq) in toluene (3 to 7.8 mL/mmol) under N2, was added BINAP (0.2 to 0.3 eq) and Pd2(dba)3 (0.1 to 0.15 eq). The rxn mixture was flushed with N2, heated under stirring at a given temperature for a given time (see Table ). It was partitioned between water and EtOAc or DCM and the org. phase was washed with brine, dried over MgS04 and concentrated in vacuo. The crude was purified by CC using Hept/EtOAc or DCM/MeOH. When necessary, an additional purification by prep. LC-MS using methods 1, 3, 4, 5, 6 or 10 was performed.

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

Reference:
Patent; IDORSIA PHARMACEUTICALS LTD; FROIDEVAUX, Sylvie; HUBLER, Francis; MURPHY, Mark; RENNEBERG, Dorte; STAMM, Simon; (266 pag.)WO2019/137927; (2019); A1;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics