Category: chlorides-buliding-blocks

Synthetic Route of 14862-52-3, A common heterocyclic compound, 14862-52-3, name is 3,5-Dibromochlorobenzene, molecular formula is C6H3Br2Cl, 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.

In the round bottom flask was charged with 1,3-dibromo-5-chlorobenzene, 25g (92.47mmol) and 31.3g (184.9mmol) of diphenylamine , 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 acteate 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 34.7g (84% yield) was purified by chromatography to the desired compound of intermediate M-10 as a white solid.

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

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;,
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Synthetic Route of 15205-11-5, A common heterocyclic compound, 15205-11-5, name is 2-Chloro-4-fluorobenzylamine, molecular formula is C7H7ClFN, 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.

Example 281-[(2-Chloro-4-fluorophenyl)methyl]-4-(4-fluoro-2,6-dimethylphenyl)-2,3- piperazinedione (E28)Methyl [(4-fluoro-2,6-dimethylphenyl)(2-oxoethyl)amino](oxo)acetate (0.15 g, 0.49 mmol) was dissolved in dichloromethane (5 ml) and cooled to O0C. 4 Angstrom molecular seives (0.3 g, 0.49 mmol), acetic acid (0.09 ml, 1.48 mmol), 2-chloro-4- fluorobenzylamine (0.07 ml, 0.54 mmol) and sodium triacetoxyborohydride (0.16 g, 0.74 mmol) were added. After 5 minutes, the reaction was warmed to room temperature and stirred for 16 hours overnight. Saturated aqueous sodium bicarbonate (5 ml) was added and the mixture stirred for 10 minutes. The organic layer was separated using a hydrophobic frit and concentrated in vacuo. The crude material was purified by mass-directed automated HPLC to yield 1-[(2-chloro-4- fluorophenyl)methyl]-4-(4-fluoro-2,6-dimethylphenyl)-2,3-piperazinedione (0.083 g) as a white solid. LC/MS [M+H]+ = 379, retention time = 2.84 minutes.

The synthetic route of 15205-11-5 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; GLAXO GROUP LIMITED; CHAMBERS, Laura Jane; DEAN, David Kenneth; MUNOZ-MURIEDAS, Jorge; STEADMAN, Jon Graham Anthony; WALTER, Daryl Simon; WO2010/125103; (2010); A1;,
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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. 694-80-4, name is 1-Bromo-2-chlorobenzene, A new synthetic method of this compound is introduced below., Recommanded Product: 1-Bromo-2-chlorobenzene

1L three bottles,To a solution of 32.5 g of 2,4,6-triisopropylbromobenzene,5.6 g of magnesium turnings and 300 mL of anhydrous THF,20 g of o-chlorobromobenzene was dropwise added,2,4,6-triisopropyl-2-bromobiphenyl Grignard reagent,Refluxed for 2 hours,Down to room temperature,2.4 g of tetrakis (triphenylphosphine) palladium was added,Stirred for 30 minutes,18.8 g of di-tert-butylphosphonium chloride was added dropwise at room temperature,The reaction was refluxed for 5 hours.And the mixture was added dropwise to the reaction solution under ice-water bath200 mL of saturated aqueous ammonium chloride was quenched,Liquid separation,The organic phase is dissolved,Add methanol crystallization,And filtered to obtain 41.7 g of white 2-di-tert-butylphosphine-2,4,6-triisopropylbiphenyl,Yield 94%.

The synthetic route of 694-80-4 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Panjin Gelin Kaimo Technology Co., Ltd.; Rao, Zhihua; Gong, Ningrui; (12 pag.)CN105859774; (2016); A;,
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13745-86-3, name is 11-Chlorodibenzo[b,f][1,4]thiazepine, 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 11-Chlorodibenzo[b,f][1,4]thiazepine

(b) 11-Piperazinyl-dibenzo[b,f][1,4]thiazepine. Piperazine (1.7 mole) was dissolved in warm toluene (about 50C.) (750 ml) and 11-chloro-dibenzo[b,f][1,4]thiazepine was added. The reaction was heated to reflux and maintained at this temperature for 5 hours. After cooling to ambient temperature the reaction was filtered to remove piperazine hydrochloride, and the organic phase was washed several times with water to remove excess piperazine. The organic phase was dried over magnesium sulfate and after filtration the solvent was removed in vacuo to give the product as an oil. The oil was dissolved in ethanol and treated with a solution of hydrogen chloride in ethanol. 11-Piperazinyl-dibenzo[b,f][1,4]thiazepine was isolated as the dihydrochloride salt in about 88% yield.

The synthetic route of 13745-86-3 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; ICI Americas Inc.; US4879288; (1989); A;,
Chloride – Wikipedia,
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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;,
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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;,
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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;,
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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

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

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;,
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