Category: 694-80-4

Synthetic Route of 694-80-4, A common heterocyclic compound, 694-80-4, name is 1-Bromo-2-chlorobenzene, molecular formula is C6H4BrCl, 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.

III – 1 raw materials (0.5g, 2 . 6mmol) dissolved in 42 ml in the mixed solvent (toluene/ethanol/water, 3:1: 3, v/v/v), adding raw material III – 2 (0.3g, 2 . 6mmol), triphenyl phosphorus palladium (0.15g, 0 . 13mmol), anhydrous sodium carbonate (0.69g, 6 . 5mmol), under the protection of nitrogen, 60 C heating reaction 24h. After the reaction cooled to room temperature, water 20 ml dilution, diatomite groundwork for filtering, ethyl acetate (15 ml × 3) washing the filter cake, the filtrate with ethyl acetate (30 ml × 4) extraction, the combined organic phase to saturated NaCl solution (20 ml × 2) washing, to obtained organic phase dried with anhydrous sodium sulfate, filtered, filtrate is decompressed and evaporate the solvent, the residue by column chromatography (petroleum ether/ethyl acetate, 70:30, v/v) to obtain the gray solid 0.47g, yield 84%.

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; China Pharmaceutical University; Huang Wenlong; Qian Hai; Liu Chunxia; (26 pag.)CN106748922; (2017); A;,
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 694-80-4 as follows. category: chlorides-buliding-blocks

General procedure: Step 1: The substituted bromobenzene (1 equiv) and (3-formylphenyl)boronic acid or (4-formylphenyl) boronic acid (1 equiv) were dissolved in a mixture of 1M sodium carbonate aqueous solution (15mL), EtOH (5mL) and toluene (15mL). After nitrogen substitution, Pd(PPh3)4 (0.05 equiv) was added. The reaction mixture was stirred at 80C under nitrogen atmosphere for 12h. The reaction mixture was cooled, and water (15mL) was added. The mixture was diluted with AcOEt (15mL), and the insoluble material was filtered off through Celite. The organic layer of the filtrate was washed with brine, dried over anhydrous sodium sulfate, and concentrated in vacuo. The residue was purified by silica gel column chromatography using a mixture of petroleum ether/ethyl acetate (10:1, v/v) as eluent to afford the desired product 2a-r, 5a and 5b as a solid. Step 2: To a solution of 2a-r, 5a or 5b (1 equiv) in MeOH (10mL) and THF (20mL) was added portionwise sodium borohydride (3 equiv) at 0C and the mixture was stirred at 0C for 1h. The reaction mixture was pouring into ice water (10mL), and extracted with ethyl acetate (3×15mL), the organic fractions were combined, washed with saturated brine (2×15mL) prior to drying over anhydrous sodium sulfate. After filtration and concentrate using a rotary evaporator, the residue was used in next step without further purification. To a solution of the obtained solid (1 equiv) in dichloromethane (20mL) was slowly added thionyl chloride (6 equiv) and a catalytic amount of DMF at room temperature. After stirring at 40C for 4h, the reaction was concentrated under reduced pressure. The residue was purified by silica gel column chromatography using a mixture of petroleum ether/ethyl acetate (20:1, v/v) as eluent to afford the desired product.

According to the analysis of related databases, 694-80-4, the application of this compound in the production field has become more and more popular.

Reference:
Article; Li, Zheng; Liu, Chunxia; Xu, Xue; Qiu, Qianqian; Su, Xin; Dai, Yuxuan; Yang, Jianyong; Li, Huilan; Shi, Wei; Liao, Chen; Pan, Miaobo; Huang, Wenlong; Qian, Hai; European Journal of Medicinal Chemistry; vol. 138; (2017); p. 458 – 479;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

Electric Literature of 694-80-4, 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. 694-80-4 name is 1-Bromo-2-chlorobenzene, 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.

General procedure: To a round bottle with a magnetic stir bar, ligand (0.01% mmol), PdCl2 (0.01% mmol), aryl halides (1.0 mmol), phenylboronic acid (1.2 mmol), K2CO3 (2.0 mmol) and 6 ml of solvent were added. The reaction mixture was conducted at room temperature for the required time, and then the solvent was removed under reduced pressure. The residual was diluted with Et2O (5 mL), followed by extraction twice (2×5 mL) with Et2O. The organic layer was dried with anhydrous MgSO4, filtered and evaporated under vacuum. The conversions rates were analyzed by gas chromatography, based on the peak area normalization method. The corrected factor was determined by samples against a standard of n-heptane. The crude products were purified by silica-gel column chromatography using petroleum ether-ethyl acetate (20:1) as an eluent, and the isolated yield was then calculated based on the feeding of the aryl halide. The isolated corresponding products were characterized by 1H NMR and 13C NMR.

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

Reference:
Article; Zhou, Zhen; Cao, Gao; Liu, Ning; Chemistry Letters; vol. 48; 6; (2019); p. 547 – 550;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

These common heterocyclic compound, 694-80-4, name is 1-Bromo-2-chlorobenzene, 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. Application In Synthesis of 1-Bromo-2-chlorobenzene

REFERENCE EXAMPLE 10; 2-(2-Chlorophenyl)-6-methoxy-1 ,2,3,4-tetrahydroisoquinolin-1 -one; To a solution of 6-methoxy-1 ,2,3,4-tetrahydroisoquinolin-1-one (1.50 g, 8.5 mmol, obtained in reference example 9) in /V-methylpyrrolidone (4 ml_) under argon, 1- EPO bromo-2-chlorobenzene (2.34 g, 12.3 mmol), copper (I) iodide (0.33 g, 1.7 mmol) and potassium carbonate (2.33 g, 16.9 mmol) were added and the mixture was heated at 200 0C overnight. It was allowed to cool and CHCI3 and 1 N NaOH were added. The phases were separated and the aqueous phase was reextracted 2 times with CHCI3. The combined organic phases were dried over Na2SO4 and the solvent was evaporated. The crude product thus obtained was purified by chromatography on silica gel using hexane-EtOAc mixtures of increasing polarity as eluent, to afford 2.01 g of the desired compound (yield: 77%). LC-MS (method 1): tR = 8.05 min; m/z = 288.1/290.1 [M+Hf.

The synthetic route of 1-Bromo-2-chlorobenzene has been constantly updated, and we look forward to future research findings.

Reference:
Patent; J. URIACH Y COMPANIA S.A.; WO2007/337; (2007); A1;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

Electric Literature of 694-80-4, 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. 694-80-4, name is 1-Bromo-2-chlorobenzene belongs to chlorides-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below.

General procedure: A mixture of the aryl halide(1 mmol), phenylboronic acid (0.1463 g, 1.2 mmol) or Ph4BNa (0.0855 g, 0.25 mmol),K2CO3 (0.2764 g, 2 mmol), ortho-palladated complex (0.0006 g, 0.1 mmol%) was addedto ethanol (2 ml) in round-bottom flask equipped with condenser and placed into theMilestone microwave oven. Initially the microwave irradiation was set at 600 W and thetemperature was raised to the desired temperature of 60C and the reaction mixture washeld at this temperature until the reaction was completed. The direct control of reactionmixture temperature was carried out using the IR sensors and software that enables on-linetemperature-pressure control by regulation of microwave power output. The mixture wasstirred continuously during the reaction and monitored by both TLC and GC. After thereaction was completed, the mixture was cooled to room temperature and was diluted withether (2 × 10 ml) and water (10 ml). The organic phase was dried overMgSO4, filtered andconcentrated under reduced pressure using a rotary evaporator. The residue was purified bysilica gel column chromatography (n-hexane:EtOAc, 9:1). The products were characterizedby comparing their mp., IR, 1H, 13C NMR spectra with those reported in the literature.Also Suzuki cross coupling reaction was carried out successfully in larger scale(30 mmol of aryl halide) using this ortho-palladated complex (0.018 g).

The synthetic route of 1-Bromo-2-chlorobenzene has been constantly updated, and we look forward to future research findings.

Reference:
Article; Hajipour, Abdol Reza; Rafiee, Fatemeh; Organic Preparations and Procedures International; vol. 45; 6; (2013); p. 465 – 472;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

Adding a certain compound to certain chemical reactions, such as: 694-80-4, name is 1-Bromo-2-chlorobenzene, 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 694-80-4, Quality Control of 1-Bromo-2-chlorobenzene

General procedure: A 10 mL Schlenk tube equipped with a magnetic stirring bar was charged with 2-arylimidazo[1,2-a]pyridine 1 (0.2 mmol, 1.0 equiv), o-dihaloarene2 (0.3 mmol, 1.5 equiv), and K2CO3 (82.9 mg, 0.6 mmol, 3.0 equiv). To this mixture were added Pd(OAc)2 (0.02 mmol, 4.5 mg)and Xphos (0.04 mmol, 19.1 mg), followed by DMF (2.0 mL) via a syringe at r.t. The tube was sealed and kept in a preheated oil bath at 160 C for 24 h. The mixture was cooled to r.t., quenched with H2O (5mL), and diluted with CH2Cl2 (10 mL). The layers were separated and the aqueous layer was extracted with CH2Cl2 (3 × 5 mL). The combined organic extracts were dried (Na2SO4), filtered, and concentrated in vacuo. The crude product was then purified by flash chromatography on silica gel (H), eluting with 5-20% EtOAc-petroleum ether.

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; Wang, Hanyang; Chen, Chunxia; Huang, Zhangjie; Yao, Liping; Li, Bin; Peng, Jinsong; Synthesis; vol. 47; 16; (2015); p. 2457 – 2466;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

Reference of 694-80-4, These common heterocyclic compound, 694-80-4, name is 1-Bromo-2-chlorobenzene, 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.

Add to Schlenk tubeN- (2-mercapto) acetamide(0.3 mmol, 50.1 mg), FeSO47H2O (0.06 mmol, 16.68 mg),1,10-lindolinol (0.06 mmol, 10.8 mg) andPotassium tert-butoxide (1.2 mmol, 134.4 mg)With nitrogen to protect the reaction system (pumping gas three times),1,2-dibromobenzene (0.45 mmol, 105.2 mg) and DMF (2 mL) were added to the reaction system with a syringe,Heated to 135 C,Stirring reaction 24hAfter completion of the reaction, the mixture was cooled to room temperature,20 mL of water was added and extracted three times with ether,The organic phase was washed with water, dried over anhydrous sodium sulfate,Column chromatography to obtain the product10H-phenothiazine. Yield 70%.Using a method similar to that of Example 1,Respectively, with o-bromobenzene,O-bromochlorobenzene,O-chlorobenzene,O-dichlorobenzene was used in place of o-dibromobenzene in Example 1 to give the product phenothiazine in a yield of 72%, 81%80%, 20%.

Statistics shows that 1-Bromo-2-chlorobenzene is playing an increasingly important role. we look forward to future research findings about 694-80-4.

Reference:
Patent; Suzhou University; Zhang, Songlin; Hu, Weiye; Zheng, Songlin; Wu, San; Wang, Ru; Zhang, Fang; (7 pag.)CN104311508; (2017); B;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

Synthetic Route of 694-80-4, 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. 694-80-4, name is 1-Bromo-2-chlorobenzene belongs to chlorides-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below.

2-nitroaniline 6.9g 49.95mmol in toluene (100mL), bromochlorobenzene 9.56g (49.95mmol), tris(dibenzylideneacetone) dipalladium(0)(tris(dibenzylideneacetone)dipalladium(0)), 1.44g (2.5mmol) , BINAP 2.33g (3.75mmol), was put cesium carbonate(caesium carbonate) 32.6g (99.91mmol) was refluxed at 120 C under a nitrogen atmosphere. After the reaction was completed after the filters using a Celite (celite) and Florisil (florisil) and washed with MC. By column chromatography and purified using an MC and Hex to give the title compound 1-5 10.7g (86%).

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, 1-Bromo-2-chlorobenzene, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; Hee SungMaterial Co., Ltd; Go, Hay Jin; Kim, Sin Tae; Kim, Gi Yong; Lee, Do Hyung; Uhm, Sung Jin; Lee, Ju Dong; (37 pag.)KR2015/30056; (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. 694-80-4, name is 1-Bromo-2-chlorobenzene, This compound has unique chemical properties. The synthetic route is as follows., Recommanded Product: 694-80-4

General procedure: A mixture of TBAF·3H2O (1.2 mmol) and triethoxy(phenyl)silane (1.2 mmol) in DMF (2 ml) was stirred at room temperature for 1 h, then the aryl halide (1 mmol) and ortho-palladated catalyst (0.4 mol %) were added and the mixture placed into a Milestone microwave reactor. Initially the microwave irradiation was set at 600 W, and the temperature was ramped from room temperature to the desired temperature (100 C). Once this was reached, the mixture was held at this temperature until the reaction was complete. The mixture was stirred continuously and monitored by both TLC and GC. After the reaction was complete, the mixture was cooled to room temperature, and was extracted with Et2O (30 ml). The organic phase was washed with H2O (30 ml), and dried over MgSO4, filtered, and concentrated under reduced pressure using a rotary evaporator. The residue was purified by silica gel column chromatography.

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 694-80-4.

Reference:
Article; Hajipour, Abdol Reza; Rafiee, Fatemeh; Tetrahedron Letters; vol. 53; 35; (2012); p. 4661 – 4664;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

Some common heterocyclic compound, 694-80-4, name is 1-Bromo-2-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. Recommanded Product: 694-80-4

General procedure: In a Schlenk flask under N2 atmosphere, 2a (5 mg, 0.011 mmol), PdCl2 (2 mg, 0.011 mmol), Cs2CO3 (358 mg, 1,1 mmol) and DMF(1.5 mL) were added. The reaction mixture was heated at 90 C for 30 min. Then, an aryl halide (1.0 mmol) and an olefin (1.2 mmol)were added and the mixture was further stirred at 125 C under air atmosphere conditions. The reaction progress was monitored by Thin Layer Chromatography (EtOAc/hexane, 1:9). After completion of the reaction, the mixture was cooled to room temperature, and water (8 mL) was added and was extracted with EtOAc (3 10 mL).The organic solvent was dried over Na2SO4 and was evaporated under vacuum to give the crude product which was further purified by column chromatography using EtOAc/hexane, 1:9.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 694-80-4, its application will become more common.

Reference:
Article; Takallou, Ahmad; Habibi, Azizollah; Halimehjani, Azim Ziyaei; Balalaie, Saeed; Journal of Organometallic Chemistry; vol. 888; (2019); p. 24 – 28;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics