Month: March 2021

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. 2106-02-7, name is 2-Chloro-4-fluoroaniline, A new synthetic method of this compound is introduced below., name: 2-Chloro-4-fluoroaniline

Lithium hexamethyldisilazide (22.9 ml, 22.9 mmol, 1 M solution in tetrahydrofuran) wasadded over 5 mm to solution of 2-chloro-4-fluoroaniline (1 .84 g, 12.6 mmol, Gas No 2106-02-7) in tetrahydrofuran (60 ml) at -780 and the mixt ure was stired at -780 for 1 h. A solution of ethyl 4-{[tert-butyl(dimethyl)silyl]oxy}- 1 -(2-ch loroethyl)cyclohexanecarboxylate (mixture of cis-/trans-isomers) (4.00 g, 11 .5 mmol) in tetrahydrofuran (60 ml) was added and the mixture was stirred for 2 h at -780 and the for 3 days at room temperature. For work-up, the reactionmixture was poured into a mixture of water and saturated sodium bicarbonate solution, extracteted with ethyl acetate (3x) and the combined organic phases were washed with brine, filtrated through a silicone filter and concentrated under reduced pressured. The residue was purified by flash chromatography (Snap Gartdidge, hexanes/ethyl acetate gradient) to give 8-{[tert-butyl(dimethyl)silyl]oxy}-2-(2-chloro-4-fluorophenyl)-2-azaspiro[4.5]decan-1 -one in 2 fractions. Fraction 1 (1.88 g, isomer 1, conatains ca 2Omol%2-chloro-4-fluoroaniline) and fraction 2 (485 mg, isomer 2).

The synthetic route of 2106-02-7 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; BAYER PHARMA AKTIENGESELLSCHAFT; EIS, Knut; ACKERMANN, Jens; WAGNER, Sarah; BUCHGRABER, Philipp; SUeLZLE, Detlev; HOLTON, Simon; BENDER, Eckhard; LI, Volkhart; LIU, Ningshu; SIEGEL, Franziska; LIENAU, Philip; BAIRLEIN, Michaela; VON NUSSBAUM, Franz; HERBERT,Simon; KOPPITZ, Marcus; (734 pag.)WO2016/177658; (2016); 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. 13526-66-4, name is 3-Bromo-6-chloroimidazo[1,2-b]pyridazine, This compound has unique chemical properties. The synthetic route is as follows., Formula: C6H3BrClN3

Intermediate P3-Bromo-6-(3-chlorophenoxy)imidazo[1,2-b]pyridazineVariant 3: 5 g (21.5 mmol) of 3-bromo-6-chloroimidazo[1,2-b]pyridazine, 3 g (23.7 mmol) of 3-chlorophenyl, 246 mg (0.27 mmol) of tris(dibenzylidineacetone)dipalladium, 500 mg of rac-BINAP and 4.1 g of sodium tert-butoxide are stirred in a mixture of 100 ml of dimethylformamide and 200 ml of tetrahydrofuran at 100 C. under a protective gas atmosphere for 12 h.The reaction mixture is then mixed with saturated sodium chloride solution. The aqueous phase is extracted with ethyl acetate. The organic phase is washed twice with dilute aqueous NaCl solution and once with saturated aqueous NaCl solution and dried over sodium sulfate. In the final purification by chromatography on silica gel, 2.78 g (40%) of the desired product were isolated.1H-NMR (DMSO-D6): delta=7.22 (d, 1H); 7.31-7.42 (m, 2H); 7.51 (d, 1H); 7.55 (t, 1H); 7.83 (s, 1H); 8.25 (d, 1H) ppm.MS (ESI): m/z=324/326 [M+H]+

According to the analysis of related databases, 13526-66-4, the application of this compound in the production field has become more and more popular.

Reference:
Patent; PRIEN, Olaf; Eis, Knut; Bader, Benjamin; Guenther, Judith; Von Bonin, Arne; US2009/93475; (2009); A1;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

Reference of 210532-25-5,Some common heterocyclic compound, 210532-25-5, name is 3,5-Difluorobenzene-1-sulfonyl chloride, molecular formula is C6H3ClF2O2S, 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 solution of 3,5-difluorobenzenesulfonyl chloride (1.1 eq., 2.62 g) in dry dichloromethane (15 mL) was added dropwise to a stirred solution of 3-[4-(4-methyl- piperazin- 1 -yl)-2-nitro-benzoylamino]-4,5,6,7-tetrahydro-pyrazolo[4,3-c]pyridine- 1 – carboxylic acid ethyl ester dihydrochloride (5.7g, 10.85 mmol) and N,N- diisopropylethylamine (6 eq., 11.34 mL) in dry dichloromethane (100 mL) at room temperature. Stirring was continued for 20 hours. The reaction mixture was then washed with water (2×80 mL), saturated sodium hydrogenocarbonate (2×80 mL), brine (80 mL), dried over sodium sulfate, evaporated to dryness and purified by flash chromatography on silica gel, using acetone-dichlorometane 60:40 as eluant. The title compound was obtained as yellow powder (5g, 73% yield).IH-NMR (400 MHz), delta ppm, DMSOtZ6): 11.21 (s, IH), 7.67 (m, 2H), 7.54 (m, 2H), 7.44 (d, J2=2.44 Hz, IH), 7.27 (dd, Jl=8.78 Hz, J2=2.44 Hz, IH), 4.37 (q, J=7.07 Hz, 2H), 4.14 (s, 2H), 3.55 (m, 2H), 3.34 (m, 4H), 3.02 (m, 2H), 2.52 (m, 4H), 2.25 (s, 3H), 1.33 (t, J=7.07 Hz, 3H).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 3,5-Difluorobenzene-1-sulfonyl chloride, its application will become more common.

Reference:
Patent; NERVIANO MEDICAL SCIENCES S.r.l.; WO2007/68619; (2007); A1;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

Adding a certain compound to certain chemical reactions, such as: 43141-66-8, name is 1-Chloro-4-(difluoromethyl)benzene, 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 43141-66-8, name: 1-Chloro-4-(difluoromethyl)benzene

Synthesis of compound 21 Bromine (17 muL; 0.34 mmol; 1.1 eq.) is added to a quartz reactor under an inert atmosphere, which is surmounted by a mercury vapour UV lamp equipped with a cooling system, and which contains a solution of para-chloro (difluoromethyl) benzene20 (50 mg; 0.3 mmol; 1 eq.) in carbon tetrachloride (5 mL; distilled over P2O5) and potassium carbonate (0.212 g; 1.54 mmol; 5 eq.). The reaction medium is refluxed and is irradiated for 5 h (84% conversion rate determined by GC). The mixture is then filtered and concentrated. The product 2j_ is involved in the following step without purification.2h C7H4BrClF2 M = 241.46 g.mol”1NMR 19F (CDO1. 282.5 Mz): – 43.9 (s, 2F). Mass: (IE): (M +) 240-242-244.

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; TFCHEM; WO2009/121939; (2009); A2;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

39191-07-6, name is 1-(3-Chlorophenyl)-N-methylmethanamine, 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: C8H10ClN

General procedure: To a solution of 1,4-bis(bromomethyl)benzene (1 mmol) in anhydrous acetonitrile (10 mL) was added potassium carbonate (3 mmol) and the corresponding secondary amine (2.2 mmol). The reaction mixture was heated at reflux for 3 h. The resulting mixture was diluted with water (20 mL) and extracted with ethyl acetate (15 mL) three times. The combined organic layers were washed with brine, dried over anhydrous sodium sulfate, and concentrated in vacuo. The crude was purified by column chromatography with methanol/dichloromethane (150:1, v/v) to give the title compound as a colorless liquid or a white solid.

The synthetic route of 39191-07-6 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Bai, Renren; Liang, Zhongxing; Yoon, Younghyoun; Liu, Shuangping; Gaines, Theresa; Oum, Yoonhyeun; Shi, Qi; Mooring, Suazette Reid; Shim, Hyunsuk; European Journal of Medicinal Chemistry; vol. 118; (2016); p. 340 – 350;,
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. 6579-54-0, name is 2,6-Dichlorobenzenesulfonyl chloride, A new synthetic method of this compound is introduced below., Quality Control of 2,6-Dichlorobenzenesulfonyl chloride

2.6-Dichlorobenzenesulfonyl chloride (100 mg, 0.41 mmol) was dissolved in DCM (0.5 mL) and triethylamine (0.11 mL, 0.81 mmol) was added followed by 2-(2- fluorophenyl)ethanamine (0.09 mL, 0.69 mmol). The reaction mixture was stirred for 1.5 hour at room temperature. DCM (10 mL) and brine (10 mL) were added to the mixture. The layers were separated and the organic phase was dried over magnesium sulfate, filtered and the solvent was evaporated. Purification by column chromatography on silica gel with petroleum ether/DCM (60:40 to 40:60) afforded the title compound as white solid (74 mg, 52 %). 1H NMR (400 MHz, CDCfi) d 2.88 (t, J = 6.9 Hz, 2H), 3.36-3.46 (m, 2H), 5.31 (t, J = 5.7 Hz, 1H), 6.95-7.02 (m, 1H), 7.05 (td, J = 7.5, 1.0 Hz, 1H), 7.14 (td, J = 7.5, 1.6 Hz, 1H), 7.17-7.24 (m, 1H), 7.32 (dd, J = 8.7, 7.3 Hz, 1H), 7.43 (s, 1H), 7.45 (d, J = 0.7 Hz, 1H). MS ESI+ m/z 348 [M+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; GLUCOX BIOTECH AB; WIKSTROeM, Per; WALUM, Erik; (126 pag.)WO2019/215291; (2019); A1;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

Reference of 18655-50-0, 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 18655-50-0 as follows.

EXAMPLE 5 2-[N-(3-(p-Chlorophenyl)propylamino)]-5-hydroxy-4-methylpyrimidine [Formula I: R=H; R’=pCl-C6 H4 (CH2)3 ] A mixture of 2.5 g (0.02 mole) of 5-acetyl-2-aminooxazole, 10.5 g (0.062 mole) of 3-(p-chlorophenyl)propylamine, and 2.7 ml of water was heated at 110 C. (external) for 16 hours. The mixture was allowed to cool to room temperature and diluted with 15 ml of water. The resulting precipitate, which is 2-[N-(3-(p-chlorophenyl)propylamino)]-5-acetyl-1H-imidazole, was collected and set aside. Concentration of the filtrate afforded as oil which was chromatographed over silica gel using 1:1 ethyl acetate/hexane as eluent. The less polar material was the desired product which was isolated as a solid. Recrystallization from acetonitrile afforded 0.71 g (13%) of the title compound, mp 99-100 C.

According to the analysis of related databases, 18655-50-0, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Pfizer Inc.; US4554276; (1985); A;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

Synthetic Route of 1005-56-7, These common heterocyclic compound, 1005-56-7, name is O-Phenyl carbonochloridothioate, 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: Phenyl chlorothionoformate (345 mg, 2.0 mmol), amine 2 (4.0 mmol) and water (15 mL) were added successively to a 50 mL round-bottom flask. The reaction mixture was stirred at room temperature for 1 h (monitored by TLC). After the reaction was complete, the solid was filtered off, washed with 10% HCl (2 ¡Á 20 mL) and deionised water(2 ¡Á 20 mL), and dried under vacuum to give the pure thiocarbamates 3. All products are known compounds and were identified by comparison of their physical and spectral data with those reported inthe literature.28

The synthetic route of 1005-56-7 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Li, Zhengyi; Chen, Yuan; Yin, Yue; Wang, Zhiming; Sun, Xiaoqiang; Journal of Chemical Research; vol. 40; 11; (2016); p. 670 – 673;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

Related Products of 33863-76-2, 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. 33863-76-2 name is 1-Bromo-3-chloro-5-fluorobenzene, 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.

Preparation 23:TERT-BUTYL 4-(3-CHLORO-5-FLUOROPHENYL)-4-HYDROXYPIPERIDINE-l-CARBOXYLATE Preparation according to preparation 1 : l-bromo-3-chloro-5-fluorobenzene (7.5 g, 35.9 mmol), tetrahydrofuran (100 ml), n-butyl lithium (2.5 M in hexane, 20 ml, 40 mmol), 4- boc-l-piperidone (7.8 g, 39.5 mmol). Yield: 8.75 g. MS m/z (rel. intensity, 70 eV) 329 (M+, 2), 255 (32), 211 (12), 157 (14), 57 (bp).

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

Reference:
Patent; A. CARLSSON RESEARCH AB; WO2007/65655; (2007); A1;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

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. Safety of 4-Bromo-3-chloroanisole

A solution of PdCl2(dppf)-DCM adduct (0.922 g, 1.129 mmol), methylboronic acid (2.70 g, 45.2 mmol), 4-bromo-3-chloroanisole (6.39 ml, 45.2 mmol), and potassium phosphate (28.8 g, 135 mmol) in 150 mL dioxane and 50 mL water was heated to 110 C. for 2 hours. The reaction mixture was then diluted with heptane, the organics dried over MgSO4 and concentrated to afford 2-chloro-4-methoxy-1-methylbenzene. m/z (ESI) 141.0 (M-CH3)+.

The synthetic route of 50638-46-5 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Amgen Inc.; Weiss, Matthew; Boezio, Alessandro; Boezio, Christiane; Butler, John R.; Chu-Moyer, Margaret Yuhua; Dimauro, Erin F.; Dineen, Thomas; Graceffa, Russell; Guzman-Perez, Angel; Huang, Hongbing; Kreiman, Charles; La, Daniel; Marx, Isaac E.; Milgrim, Benjamin Charles; Nguyen, Hanh Nho; Peterson, Emily; Romero, Karina; Sparling, Brian; US9212182; (2015); B2;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics