Month: July 2021

Application of 14862-52-3,Some common heterocyclic compound, 14862-52-3, name is 3,5-Dibromochlorobenzene, molecular formula is C6H3Br2Cl, 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.

In the round bottom flask was charged with 1,3-dibromo-5-chlorobenzene 25g (92.47mmol) and methyl diphenyl amine 33.9g (184.9mmol) into a sodium t- butoxide 26.7g (277.41mmol) was added to 463ml toluene dissolved. Here Pd (dba)2 0.266g (0.462mmol) and tri-tert-butylphosphine was put 0.187g (0.924mmol) in turn and the mixture was stirred under reflux for 4 hours under a nitrogen atmosphere. After the reaction the organic layer was then extracted with ethyl acetate dry distilled over magnesium sulfate, filtered and the filtrate was concentrated under reduced pressure. The product n- hexane / dichloromethane (9: 1 by volume) to yield the silica gel column 37.3g (yield 85%) of intermediate M-11 the desired compound is purified by chromatography as a white solid.

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-Dibromochlorobenzene, its application will become more common.

Reference:
Patent; Chei Industries Inc.; Ryu, Dong Wan; Heo, Dal Ho; Jung, Seong Hyeon; Hong, Jin Seok; Kim, Jun Seok; Yoo, Dong Kyu; Lee, Seung Jae; Lee, Han Il; Chang, Yu Na; Cho, Yeong Kyeong; Chae, Mi Yeong; (44 pag.)KR2016/8651; (2016); A;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

Adding a certain compound to certain chemical reactions, such as: 26487-67-2, name is 1-(2-Chloroethyl)azepane hydrochloride, 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 26487-67-2, Recommanded Product: 26487-67-2

Example 7 1-(2-(1-Perhydroazepinyl)ethyl)-3,4-dimethyl-4-(3-(1H-1,2,3-triazol-4-yl)phenyl)piperidine A solution of 1-(2-chloroethyl)perhydroazepine hydrochloride (42 mg, 0.21 mmol) in N,N-dimethylformamide (1 mL) was treated with triethylamine (30 muL, 0.22 mmol) then transferred to a flask containing 3,4-dimethyl-4-(3-(1H-1,2,3-triazol-4-yl)phenyl)piperidine (Preparation 44, 45 mg, 0.176 mmol) in N,N-dimethylformamide (2 mL). Sodium iodide (32 mg, 0.21 mmol) and sodium hydrogencarbonate (18 mg, 0.21 mmol) were added and the resultant mixture was heated at 60°C overnight. The solvent was then removed in vacuoand the residue was partitioned between saturated aqueous sodium hydrogencarbonate solution (5 mL) and dichloromethane (5 mL). The phases were separated and the aqueous layer was further extracted with dichloromethane (2 x 5 mL). The combined extracts were dried over Na2SO4, filtered and concentratedin vacuo.The residue was purified by reversed phase preparative HPLC (condition 2) to give the acetate salt of the title compound. The free base was obtained by treating with dilute aqueous ammonia solution (2 mL) and extracting with ether (4 x 3 mL). Drying over Na2SO4, filtering andevaporation to dryness gave the title compound as a white solid (16 mg, 24percent). NMR (CDCl3, selected data for the free base): 0.8 (d, 3H), 1.35 (s, 3H), 1.6-1.8 (m, 9H), 2.10 (m, 1H), 2.4-2.5 (m, 2H), 2.6-3.0 (m, 11H), 7.25 (d, 1H), 7.35 (t, 1H), 7.55 (d, 1H), 7.85 (s, 1H), 7.95 (s, 1H). MS (thermospray): M/Z (MH+) 382.6; C23H35N5+ H requires 382.3.

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

Reference:
Patent; PFIZER INC.; Pfizer Limited; EP1072601; (2001); A2;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

Application of 95-81-8, The chemical industry reduces the impact on the environment during synthesis 95-81-8, name is 2-Chloro-5-methylaniline, I believe this compound will play a more active role in future production and life.

Reference Example 12 4-Chloro-6-(2-chloro-5-methylanilino)pyrimidine Tetramethylene sulphone (10 ml) was added to 4,6-dichloropyrimidine (25.0 g, 170 mmol) and heated to 125 C. 2-Chloro-5-methylaniline (11.90 g, 84 mmol) was added portion wise over 20 mins. The reaction mixture was heated at 125 C. for 2 hours. The reaction was allowed to cool to room temperature and DCM (200 ml) was added. The mixture was basified to pH 9-10 with methanolic ammonia and evaporated onto silica (15 g). The residue was purified by column chromatography eluding with EtOAc:isohexane (10:90) to give a white solid (12.25 g, 29%). NMR (300 MHz): 2.3 (s, 3H), 6.7 (s, 1H), 7.0 (d, 1H), 7.4 (d, 1H), 7.5 (s, 1H), 8.4 (s, 1H), 9.4 (s, 1H); m/z 254 (MH+).

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-5-methylaniline, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; AstraZeneca AB; US6632820; (2003); B1;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

Application of 61881-19-4, The chemical industry reduces the impact on the environment during synthesis 61881-19-4, name is 2,2,2-Trifluoro-N-phenylacetimidoyl chloride, I believe this compound will play a more active role in future production and life.

General procedure: To an ice cooled suspension of NaH (3.3mmol) in dry THF (20mL) under nitrogen atmosphere was slowly added a solution of the ketone 8a-e(1mmol) in THF (5mL). The resulting suspension was stirred for 30min at 0C and then a solution of the corresponding trifluoroacetimidoyl chloride 9a-e (1mmol) in dry THF (3mL) was slowly added dropwise at 0C and then further stirred at room temperature for 3h. The resulting orange-brown solution was evaporated under reduced pressure, water was added carefully (20mL) and extracted with CHCl3 (2×20mL). The organic extract was separated, dried over anhydrous magnesium sulfate and evaporated obtaining a brown oil, which was further purified either by recrystallization or column chromatography (silicagel, Hex 7: EtOAc 3).

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, 2,2,2-Trifluoro-N-phenylacetimidoyl chloride, other downstream synthetic routes, hurry up and to see.

Reference:
Article; Romero, Angel H.; Salazar, Jose; Lopez, Simon E.; Journal of Fluorine Chemistry; vol. 169; (2015); p. 32 – 37;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

Synthetic Route of 94-97-3, These common heterocyclic compound, 94-97-3, name is 5-Chloro-1H-benzo[d][1,2,3]triazole, 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: A 35-mL Schlenk tube, equipped with a magnetic stirring bar, was charged with 9H-xanthene 1a (137 mg, 0.75 mmol), 1H-benzo[d][1,2,3]triazole 2a (60 mg, 0.5 mmol), and BPO (242 mg, 1.0 mmol), followed by the addition of DCE (5.0 mL). The mixture was stirred at 80 C for 6 h; then it was quenched with saturated aqueous Na2S2O3 (2.0 mL), saturated aqueous K2CO3 (2.0 mL), and water (20.0 mL), and extracted with CH2Cl2 (20.0 mL) three times. The residue obtained after evaporation of the solvent was purified by column chromatography on silica gel (petroleum ether/ethyl acetate = 12:1, v/v) to afford 1-(9H-xanthen-9-yl)-1H-benzo[d][1,2,3]triazole 3a as a colorless crystal (144 mg, 96% yield).

Statistics shows that 5-Chloro-1H-benzo[d][1,2,3]triazole is playing an increasingly important role. we look forward to future research findings about 94-97-3.

Reference:
Article; Li, Yanni; Li, Yanping; Li, Yuan; Chen, Chunlin; Ying, Fengyuan; Dong, Ying; Liang, Deqiang; Synthetic Communications; vol. 49; 16; (2019); p. 2053 – 2065;,
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. 1996-29-8, name is 1-Bromo-4-chloro-2-fluorobenzene, This compound has unique chemical properties. The synthetic route is as follows., Quality Control of 1-Bromo-4-chloro-2-fluorobenzene

General procedure: (2-Bromo-5-chloro-phenyl)hydrazine (6) A 250 mLround-bottom flask was charged with 1-bromo-4-chloro-2-fluoro-benzene (8.5 mL,68.0 mmol), hydrazine monohydrate (13 mL, 270 mmol) and dimethylsulfoxide (25mL) and the solution was stirred at 70 C for 3 days. The reaction was then cooled to room temperature and water (200 mL) was added. The precipitate was collected by filtration and dried under vacuum for 16 hours to give (2-bromo-5-chloro-phenyl)hydrazine (14.5g, 65 mmol, 96% yield) as a white solid. LCMS ES+ m/z = 221.0 [M+H]+.

According to the analysis of related databases, 1996-29-8, the application of this compound in the production field has become more and more popular.

Reference:
Article; Rene, Olivier; Fauber, Benjamin P.; Tetrahedron Letters; vol. 55; 4; (2014); p. 830 – 833;,
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 2613-30-1 as follows. HPLC of Formula: C6H4ClF2N

Anhydrous copper (II) bromide (2.7 g, 12.1 mmol) and t-butyl nitrite (1.56 g, 15.1 mmol) were combined in anhydrous acetonitrile (25 mL). The resulting mixture was heated to 65 C. and a solution of 4-chloro-2,5-difluoro-phenylamine (1.65 g, 10.1 mmol) in anhydrous acetonitrile (2 mL) was added dropwise (vigorous gas evolution was noted). After the reaction mixture cooled to ambient temperature, it was added to 2N HCl and extracted twice with diethyl ether. The organic extracts were then combined, washed with 2N HCl, washed with saturated sodium bicarbonate, dried, concentrated and purified by flash chromatography on silica gel (hexanes) to give the title compound as a white solid (1.11 g, 48.4% yield): 1H NMR (CDCl3) delta 7.38 (dd, 2H), 7.21 (dd, 2H).

According to the analysis of related databases, 2613-30-1, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Dow AgroSciences LLC; US2009/88322; (2009); A1;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

Reference of 886762-39-6,Some common heterocyclic compound, 886762-39-6, name is 3,4-Dichloro-2-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.

3,4-Dichloro-2-fluoroaniline (1.8 g, 10 mmol), 2,4-dichloropyrimidine (2.25 g, 15 mmol) and hydrochloric acid (0.5 mL, 12 M) were added to 5mL of isopropyl alcohol and then put to reflux for 2h. The reaction mixture was cooled down to room temperature and then filtered to give the title intermediate (1.2 g). m/z: ESI 292.0.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 3,4-Dichloro-2-fluoroaniline, its application will become more common.

Reference:
Patent; Ancureall Pharmaceutical (Shanghai) Co., Ltd.; SI, Jutong; WANG, Guan; YANG, Zhihe; JIANG, Meifeng; XU, Benpo; ZHOU, Chentao; (147 pag.)EP3398939; (2018); A1;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

14862-52-3, name is 3,5-Dibromochlorobenzene, 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: C6H3Br2Cl

General procedure: 3-bromo-1H-indole (5.0 g, 0.026 mol), 9H-carbazol-3-ylboronic acid (6.5 g, 0.030 mol), Pd(pph3)4 (1.5 g, 0.0013 mol), potassium carbonate (7.2 g, 0.052 mol) in THF 200 ml was reacted at 65 C for 18 hours. After reaction and cooling the H2O:MC after separation of to (n-Hexane: MC) column purification for 1-1 intermediate that is 5.2 g (71% yield) are obtained. (m/z=282). Intermediates 30-2 (4.0 g, 0.010 mol) 1,3-dibromo-5-chlorobenzene to (2.2 g, 0.008 mol) for inserting and removing manufacturing e.g. in the embodiment 1-(1) the same method used in the synthesis of 3.8 g (74% yield) is obtained. (m/z=647)

The synthetic route of 14862-52-3 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; P&H tech; Hyeon, Seo Young; Jong, Song Ok; Oh, Hyeon Jin; (92 pag.)KR2015/131700; (2015); A;,
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. 1996-29-8, name is 1-Bromo-4-chloro-2-fluorobenzene, This compound has unique chemical properties. The synthetic route is as follows., Recommanded Product: 1-Bromo-4-chloro-2-fluorobenzene

To a stirred solution of 1-bromo-4-chloro-2-fluorobenzene (5 g, 23.87 mmol) in tetrahydrofuran (40 mL) cooled to -78 C was added LDA (14.92 mL, 29.8 mmol) dropwise. The reaction mixture was stirred at this temperature for 30 min. thenallowed to warm to -20 C and stirred for 30 min. The reaction was then cooled to -78 C and trimethyl borate (3.47 mL, 31.0 mmol) dissolved in THF (5 mL) was added dropwise. The reaction mixture was warmed to -20C and stirred for 1 h. The reaction mixture was then cooled to -78 C and peracetic acid (16 mL, 84 mmol) as slowly added dropwise. The mixture was allowed to warm to rt and stirred for 12 h. The reaction mixture was again cooled to 0 C and quenched with 5% ammonium chloride The solution was extracted with ethyl acetate (2×50 mL). The combined organic layers were washed with brine (50 mL), dried over sodium sulfate, filtered and concentrated under reduced pressure to afford 3-bromo-6-chloro-2-fluorophenol (4.99 g, 18.25 mmol, 76 % crude yield) as ayellow oil. The material was carried forward without further purification.

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 1996-29-8.

Reference:
Patent; Bristol – Myers Squibb Company; Vivekanand, M.Burda; Pan, Senrian; Ramkumar, Rajamani; Sushil, Jetanand Nara; Maheswaran, Shibasanban Calatrava; Tarun Kumar, Meishar; Jonathan, L. Ditta; Carolyn, Diane Jiaba; John, J. Bronson; John, E. Maco; (232 pag.)JP2015/528018; (2015); A;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics