Month: May 2021

Some common heterocyclic compound, 108-37-2, name is 1-Bromo-3-chlorobenzene, molecular formula is C6H4BrCl, 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. name: 1-Bromo-3-chlorobenzene

General procedure: Aryl-halide (0.2 mmol, 1 equiv.), Ir(dtbbpy)(ppy)2PF6 (1.8 mg, 0.002 mmol, 1 mol %), NiI2 (3.1 mg, 0.01mmol, 5 mol %), DMSO (2.0 mL) was added to a 10 mL schlenk flask equipped with a magnetic stirrerbar. This resulting mixture was sealed and degassed via vacuum evacuation and subsequent backfill with ethylene for three times. Then, N,N,N?,N?-tetramethylethylenediamine, TMEDA (60 muL, 2 equiv.)and N,N-diisopropylethylamine, DIPEA (70 muL, 2 equiv.) were subsequently added in this order. The solution was gently bubbled with ethylene balloon for approximately 30 seconds. The solution was then taken up into a 8 mL stainless steel syringe pre-purged with argon, and quickly assembled onto thestop-flow micro tubing, SFMT setup. Solution was pumped into the SFMT at 400 muL/min while maintaining approximately 1:1 gas-liquid slug flow at 250 PSI. Filled SFMT was then irradiated with blueLED (2 meter strip, 18 W) in a 100oC oil bath for 24 hours. The SFMT was wash with DCM (8 mL) and subjected to GC analysis (Figure S5). Then water (30 mL) was added to reaction mixture and extracted with DCM (10 mL) three times. Combined organic layer was successively wash with brine three timesand dried over Na2SO4 and concentrated under reduced pressure. The residue was then subjected to flash column chromatography to yield the product as a mixture of meso/dl isomers (which could not be separated by column chromatography).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 108-37-2, its application will become more common.

Reference:
Article; Li, Jiesheng; Luo, Yixin; Cheo, Han Wen; Lan, Yu; Wu, Jie; Chem; vol. 5; 1; (2019); p. 192 – 203;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

Synthetic Route of 164648-75-3, A common heterocyclic compound, 164648-75-3, name is 4-Amino-3,5-dichlorobenzylamine, molecular formula is C7H8Cl2N2, 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 F (1): To a solution of intermediate A (9 g, 0.047 mol) in dry THF under N2, diisopropyl ethylamine (8.2 ml, 0.047 mol) was added. The reaction mixture was cooled to 0 C. and then Boc anhydride (10.26 g, 0.047 mol) dissolved in dry THF (25 mL) was added drop wise maintaining the reaction temperature at 0 C. After the addition was over, the reaction mixture was allowed to reach room temperature and stirred for about 2 hrs. After ensuring the absence of the starting material, THF was removed under the vacuum and the resulting solid was dissolved in ethyl acetate. The organic layer was washed with water (25 mL), brine (25 mL), dried over anhydrous sodium sulfate and concentrated under vacuum to afford the product as pale yellow colored solid. The product was further purified by recrystallization using pet ether/ether. (9.9 g, 72.2%)

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; Bristol-Myers Squibb Company; US2007/232581; (2007); A1;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

Adding a certain compound to certain chemical reactions, such as: 102-49-8, name is 3,4-Dichlorobenzylamine, 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 102-49-8, Recommanded Product: 3,4-Dichlorobenzylamine

General procedure: To a solution of 1-(2-hydroxy-2-phenylethyl)-5-(1H-pyrrol-1-yl)-1H-pyrazole-4-carboxylic acid 12 (3.0 g, 10mmol) in an. DMF (10 mL) cooled at 0C triethylamine (2mL), diphenylphosphorylazide (3.4 g, 12 mmol) and the suitable amine (20 mmol) were added dropwise. The reaction mixture was then heated at 30-60 C for 12 h. After cooling to room temperature, ice-water (200 mL) is added and the reaction mixture is made acid adding 1 M HCl. The obtained solid is filtered, washed several times with water and purified by recrystallization from absolute ethanol or by Silicagel chromatography (first eluent CH2Cl2, final eluent Et2O).

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:
Article; Meta, Elda; Brullo, Chiara; Tonelli, Michele; Franzblau, Scott G.; Wang, Yuehong; Ma, Rui; Baojie, Wan; Orena, Beatrice S.; Pasca, Maria R.; Bruno, Olga; Medicinal Chemistry; vol. 15; 1; (2019); p. 17 – 27;,
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. 623-12-1, name is 1-Chloro-4-methoxybenzene, This compound has unique chemical properties. The synthetic route is as follows., Recommanded Product: 623-12-1

General procedure: A 25 mL synthesizer tube was taken with a mixture of aryl halide (0.5 mmol), aryl boronic acid (0.55 mmol),base (1.5 mmol), Pd-complex C1 (0.2 mol %) and the mixture was stirred in2 mL of water at 50C for the required time. After completion, the reaction mixture was extracted with ether (3 Chi 20 mL). The combined extract was washed with brine (2 Chi 20 mL) and dried over Na2SO4. After evaporation of the solvent under reduced pressure, the residue was chromatographed (silica gel,ethyl acetate-hexane: 1:9) to obtain the desired products. The products were confirmed by comparing the 1H and 13C NMR and mass spectral data with authentic samples.

According to the analysis of related databases, 623-12-1, the application of this compound in the production field has become more and more popular.

Reference:
Article; Dewan, Anindita; Bora, Utpal; Borah, Geetika; Tetrahedron Letters; vol. 55; 10; (2014); p. 1689 – 1692;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

Adding a certain compound to certain chemical reactions, such as: 461432-23-5, name is 4-Bromo-1-chloro-2-(4-ethoxybenzyl)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 461432-23-5, name: 4-Bromo-1-chloro-2-(4-ethoxybenzyl)benzene

Compound 6 5.0g (15.4mmol) was dissolved in 20mL tetrahydrofuran and 40mL of dry toluene was dried in nitrogen atmosphere, cooled to -78 C, n-butyllithium was slowly dropwise added 10.6mL (16.94mmol, 1.6M), was added after -78 C the reaction 0.5 h, then 5mL of dry toluene was slowly added dropwise trimethylchlorosilane dissolved glucose protected lactone, addition was complete the reaction at -78 C 1h, then 10mL of methanesulfonic acid was added 3.0mL (46.2mmol dissolved in methanol ), after the addition the reaction warmed to room temperature for 16 h, after completion of the reaction, the reaction solution was added dropwise with saturated sodium bicarbonate, ethyl acetate (50mL ¡Á 3). the combined organic phases with saturated sodium bicarbonate ¡Á 2, saturated sodium chloride ¡Á 2, dried over anhydrous Na2SO4 dry. Suction filtration to give a yellow oil, toluene / petroleum ether (1:5) was recrystallized to give a pale yellow solid was separated by column chromatography (dichloromethane: methanol = 20) to give 7 as a white solid.

At the same time, in my other blogs, there are other synthetic methods of this type of compound, 4-Bromo-1-chloro-2-(4-ethoxybenzyl)benzene, and friends who are interested can also refer to it.

Reference:
Patent; CHINA PHARMACEUTICAL UNIVERSITY; HUANG, WENLONG; QIAN, HAI; WANG, XUEKUN; LI, YING; YANG, BAOWEI; LI, ZHENG; (23 pag.)CN103739581; (2016); B;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

Related Products of 626-43-7,Some common heterocyclic compound, 626-43-7, name is 3,5-Dichloroaniline, molecular formula is C6H5Cl2N, 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: Anhydrous TFA (3e5 drops) was added into appropriatelysubstituted aniline (10 mmol) and then heated to 100 C. To thismixture was added 3mL of ethyl acrylate (EA) within 10min, andthe mixture was stirred at 100 C for 24 h. After this period the EAwas removed under vacuum. The resulted residue was purified bysilica gel chromatography to yield compound 6.

The synthetic route of 626-43-7 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Liu, Qi; Shi, Wei-Kang; Ren, Shen-Zhen; Ni, Wei-Wei; Li, Wei-Yi; Chen, Hui-Min; Liu, Pei; Yuan, Jing; He, Xiao-Su; Liu, Jia-Jia; Cao, Peng; Yang, Pu-Zhen; Xiao, Zhu-Ping; Zhu, Hai-Liang; European Journal of Medicinal Chemistry; vol. 156; (2018); p. 126 – 136;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

Reference of 363-51-9, These common heterocyclic compound, 363-51-9, name is 2-Chloro-6-fluoroaniline, 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.

A mixture of 2-chloro-6-fluoroaniline (1.5 g, 10.3 mmol), pyridine (1.0 mL, 12.4 mmol), and isobutyric anhydride (2.0 mL, 12.1 mmol) was purged with nitrogen and irradiated in a microwave reactor at 150 C. for 2 hrs. After cooling to r.t., water was added and the mixture was stirred until a solid precipitate formed. The resulting solid was then collected by filtration, washed with water, and air dried to afford N-(2-chloro-6-fluorophenyl)isobutyramide in quantitative yield as an off-white solid. The crude product obtained was used directly in the next step without further purification. LCMS calculated for C10H12ClFNO (M+H)-: m/z=216.1; Found 216.1.

Statistics shows that 2-Chloro-6-fluoroaniline is playing an increasingly important role. we look forward to future research findings about 363-51-9.

Reference:
Patent; Incyte Corporation; Hummel, Joshua; Vechorkin, Oleg; Sokolsky, Alexander; Ye, Qinda; Liu, Kai; Yao, Wenqing; (60 pag.)US2020/48241; (2020); A1;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

Adding a certain compound to certain chemical reactions, such as: 62593-17-3, name is 2,4-Dichloro-6-(trifluoromethyl)aniline, 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 62593-17-3, COA of Formula: C7H4Cl2F3N

A.2.10.1 Synthesis of 2,4-dichloro-6-trifluoromethylphenylacetic acid methyl ester To a suspension of CuCI2 (3.0 mmol) in 30 mL CH3CN was added tBu-nitrite (4.1 mmol) followed by dropwise addition of 1 ,1 -dichloroethylen (39.1 mmol). A solution of 2,4- dichloro-6-trifluoromethylaniline (2.2 mmol) in 2 mL CH3CN was slowly added. After stirring at RT overnight, the reaction was quenched with 25percent aqueous HCI solution and extracted 3 times with EtOAc. The combined organic layers were dried over MgS04. After removal of the solvent the crude was redissolved in 3 mL MeOH. After addition of 2.4 mL of a 30percent solution of NaOMe in MeOH the mixture was refluxed for 5 h. Then, 1.8 mL concentrated H2S04 solution was added at RT and the mixture was heated to reflux for 1 h. After concentrating in vacuo the resulting solid was partitionned between water and DCM. The water phase was extracted 3 times with DCM. The combined organic layers were dried over MgS04. Purification with CC using Hept/EtOAc (10/1 ) gives the desired product as yellowish oil. LC-MS (A): tR = 0.93 min; 1H NMR ((CD3)2SO) delta: 8.1 1 (s, 1 H), 7.88 (s, 1 H), 3.97 (s, 2H), 3.65 (s, 3H).

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, 2,4-Dichloro-6-(trifluoromethyl)aniline, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; ACTELION PHARMACEUTICALS LTD; HILPERT, Kurt; HUBLER, Francis; KIMMERLIN, Thierry; RENNEBERG, Dorte; STAMM, Simon; WO2013/108227; (2013); A1;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

Adding a certain compound to certain chemical reactions, such as: 106131-61-7, name is 3,6-Dichloro-1,2,4,5-tetrazine, 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 106131-61-7, COA of Formula: C2Cl2N4

General procedure: In a 100 mL round bottom flask, was introduced the diol(0.66 mmol), s-collidine (0.79 mmol) and 20 mL of dry dichloromethane and the mixture was stirred at room temperature. 3,6-dichloro-s-tetrazine 1 (0.66 mmol) was dissolved in dry dichloromethane and added dropwise in the flask. After 2 h the reaction is complete (TLC) and the solvent was removed under reduced pressure. The crude residue was purified by column chromatography on silica gel (eluent from petroleum ether/ethyl acetate 7/3 to pure ethyl acetate).

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, 3,6-Dichloro-1,2,4,5-tetrazine, other downstream synthetic routes, hurry up and to see.

Reference:
Article; Guermazi, Refka; Royer, Lorna; Galmiche, Laurent; Clavier, Gilles; Audebert, Pierre; Hedhli, Ahmed; Journal of Fluorescence; vol. 26; 4; (2016); p. 1349 – 1356;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

These common heterocyclic compound, 918538-05-3, name is 2,4-Dichloropyrrolo[2,1-f][1,2,4]triazine, 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. HPLC of Formula: C6H3Cl2N3

116A. Preparation of 7-bromo-2,4-dichloropyrrolo[1,2-f][1,2,4]triazine A slurry of N-bromosuccinimide (4.17 g, 23.40 mmol) in 10 mL of acetonitrile was added to a cooled (0 C.) solution of 2,4-dichloropyrrolo[1,2-f][1,2,4]triazine (4 g, 21.27 mmol) in acetonitrile over 1 h. The reaction mixture was allowed to come to room temperature and stirred for an additional 16 hr to get a solution. The solvents were evaporated to get a solid. To this residue was added dichloromethane to dissolve most of the solids and the resulting solution was loaded onto 250 gm of silica in a 350 mL coarse frit funnel (preequilibrated with 5% EtOAc in hexanes). The silica gel was washed with 5% to 50% EtOAC in hexanes. The fractions were collected and evaporated to obtain 7-bromo-2,4-dichloropyrrolo[1,2-f][1,2,4]triazine (5.29 g, 93% pure) as crystals contaminated with ~7% of the 5-bromo isomer. The mixture as such was carried to the next step without further purification. MS (ESI) m/z 266.08 (M+H).

The synthetic route of 2,4-Dichloropyrrolo[2,1-f][1,2,4]triazine has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Bristol-Myers Squibb Company; US2008/45496; (2008); A1;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics