Month: February 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. 4333-56-6, name is Bromocyclopropane, A new synthetic method of this compound is introduced below., category: bromides-buliding-blocks

To a stirred solution of 2-bromo-5-fluorophenol (1 .0 g) in DMF (15 mL) in a microwave tube was added cesium carbonate (5.0 g), potassium iodide (130 mg) and bromocyclopropane (1 .82 g). The mixture was heated in a microwave oven to 180 C for 1 h, to 200 C for 1 h and to 220 C for 1 h. Ethyl acetate was added and the mixture was washed with water. The organic phase was washed with saturated sodium chloride solution, dried (sodium sulfate) and the solvent was removed in vacuum. Silica gel chromatography gave 1 .14 g of the title compound. 1H-NMR (300MHz, DMSO-d6): delta [ppm] = 0.62 – 0.88 (m, 4H), 3.90 – 4.00 (m, 1 H), 6.77 (td, 1 H), 7.23 (dd, 1 H), 7.48 – 7.63 (m, 1 H).

The synthetic route of 4333-56-6 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; BAYER PHARMA AKTIENGESELLSCHAFT; SCHULZE, Volker; MAIS, Franz-Josef; WO2014/9219; (2014); A1;,
Bromide – Wikipedia,
bromide – Wiktionary

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. 2695-47-8, name is 6-Bromo-1-hexene, A new synthetic method of this compound is introduced below., Recommanded Product: 6-Bromo-1-hexene

General procedure: A 70 ml oven dried autoclave containing a stirrer bar wascharged the AgI (0.5 mg, 0.002 mmol) and Cs2CO3 (978 mg, 3.0mmol). The autoclave was purged three time with CO2 and theterminal alkynes 1 (2.0 mmol), bromides 2 (3.0 mmol), and dryDMF (20 ml) were then added sequentially via a syringe. Theautoclave was then sealed and pressurized to the appropriatepressure with CO2. The reaction mixture was then stirred at 60C for 24 h and the autoclave was cooled to room temperatureand the remaining CO2 slowly vented from the system. Thereaction mixture was diluted with water (30 ml) and extractedwith ethyl acetate (30 ml ¡Á 3). The combined organic layerswere washed with water and brine, dried over Na2SO4, andfiltered. The solvent was removed under vacuum. The productwas isolated by column chromatography on silica gel.

The synthetic route of 2695-47-8 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Zhang, Linlin; Zhang, Wenzhen; Shi, Linglong; Ren, Xiang; Lue, Xiaobing; Cuihua Xuebao/Chinese Journal of Catalysis; vol. 34; 6; (2013); p. 1179 – 1186;,
Bromide – Wikipedia,
bromide – Wiktionary

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. 3875-78-3, name is 6-Bromochroman belongs to bromides-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below. Formula: C9H9BrO

To a mixture of 6-bromochroman (500 mg, 2.35 mmol, 1.30 equiv) in tetrahydrofuran (10 mL) was added n-BuLi (0.94 mL, 1.30 equiv, 2.5N) at -78 C. The mixture was stirred for 30 min at -78 C. After that was added a solution of 7-bromo-4-methoxy-2,3-dihydrobenzofuran-5-carbaldehyde (465 mg, 1.81 mmol, 1.00 equiv) in tetrahydrofuran (5 mL) at -78 C. The reaction was stirred at -78 C. for 1 h. NH4Cl/H2O was added and the mixture was extracted with EtOAc thrice. The combined extracts were washed with brine and dried over Na2SO4. The mixture was then concentrated and purified by chromatography on silica gel (3:1 PE/EA) to yield (7-bromo-4-methoxy-2,3-dihydrobenzofuran-5-yl)(chroman-6-yl)methanol as a yellow oil. MS (ES) m/z: 373[M-OH]+

The synthetic route of 3875-78-3 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Janssen Pharmaceutica NV; Xu, Guozhang; Kuo, Gee-Hong; Gaul, Micheal; (68 pag.)US2019/55226; (2019); A1;,
Bromide – Wikipedia,
bromide – Wiktionary

Synthetic Route of 4263-52-9, These common heterocyclic compound, 4263-52-9, name is Sodium 2-bromoethanesulphonate, 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 reactor was charged with 54.89 g (0.186 mol) methyloleate, 9.55 g (0.093 mol) diethylenetriamine and heated under an argon atmosphere with stirring to 160 C., whereupon methanol began to reflux, enough methanol was distilled off to bring to 180 C., stirring with argon sparging was continued for 2 days to yield pure 3-(2-((z)-hepatadec-8-en- 1 -y-1 -(2-oleamido ethyl)-4,5-dihydro- 1H-imidazoline as a viscous light straw colored fluid. ?3C NMR (ppm in CDC13, 100 MHz) oe=25.8, 36.6, 38.0, 46.6, 50.2, 52.2, 167.5, 173.4. A flask was charged with 4.000 g (6.514 mmol) 3-(2-((z)-hepatadec-8-en-1-yl)-1-(2-oleamido ethyl)-4,5-dihydro-1H-imidazoline, 1.648 g (7.810 mmol) sodium 2-bromoethylsulfonate, 20 ml anhydrous N-Methyl-2-pyrrolidone (NMP), heated under an argon atmosphere with stirring at 140 C. for 2 days. Evaporated the mixture in vacuo (90 C./0.8 mmHg), poured into 30 mL sodium chloride saturated deionized water, extracted with 20 mL aliquots of chloroform until the chloroform layer had only a faint color, combined the chloroform layer and dried over anhydrous magnesium sulfate, filtered through celite, vacuum distilled. A viscous dark amber fluid comprised of about 38 wt % of 2-(2-((Z)-heptadec-8-en-1-yl)-1-(2-oleamidoethyl)-4,5-dihydro-1H-imidazol-3-ium-3-yl)ethane-1-sulfonate (z-Im-1), 48 wt % Im and 15 wt % of NMP was obtained. The product was purified using flash chromatography with MeOH-water (9:1), and yield 80 mol % of z-IM-1. 13C NMR (ppm in CDCl3, 100 MHz) delta=170.8, 46.7, 47.4, 36.0, 46.3, 174.8, 25.7, 43.4, 45.7, 362, 25.6.

Statistics shows that Sodium 2-bromoethanesulphonate is playing an increasingly important role. we look forward to future research findings about 4263-52-9.

Reference:
Patent; GPCP IP Holdings LLC; Chen, Yu; Holtman, Kevin M.; Hammes, Brian S.; Boettcher, Jeffrey J.; (31 pag.)US2018/202109; (2018); A1;,
Bromide – Wikipedia,
bromide – Wiktionary

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. 399-94-0, name is 1-Bromo-2,5-difluorobenzene belongs to bromides-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below. name: 1-Bromo-2,5-difluorobenzene

2-Bromo-1,4-difluorobenzene (53.6 g, 277.74 mmol) in THF cooled to -50 C. was added to isopropyl magnesium chloride (2M in THF) (133 mL, 266 mmol). The reaction mixture thus obtained was warmed to 0 C. and stirred for 1 h. The reaction mixture was cooled again to -50 C. 4-chloro-N-methoxy-N-methylbutanamide (40 g, 241.52 mmol) in THF (200 mL) was added dropwise to this reaction mixture with stirring and the stirring was continued at 0 C. for 1 h. The reaction mixture was quenched with saturated aqueous NH4Cl solution, extracted with ethylacetate. The organic layer collected was washed with water (500 mL) and then with brine solution, dried over anhydrous sodium sulfate and concentrated under reduced pressure to afford a crude liquid residue. The residue thus obtained was purified by column chromatography (using 60-120 silica gel and 5% EtOAc in Hexane as eluent) to afford 35 g of the title compound as a colourless liquid. 1H NMR (300 MHz, CDCl3) delta ppm 7.6-7.53 (1H, m), 7.26-7.09 (2H, m), 3.7 (2H, t) 3.22-3.14 (2H, m), 2.28-2.16 (2H, m).

The synthetic route of 399-94-0 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; DR. REDDY’S LABORATORIES LTD.; Sasmal, Pradip Kumar; Ahmed, Shahadat; Tehim, Ashok; Pradkar, Vidyadhar; Dattatreya, Prasanna M.; Mavinahalli, Nanjegowda Jagadeesh; US2014/371217; (2014); A1;,
Bromide – Wikipedia,
bromide – Wiktionary

Adding a certain compound to certain chemical reactions, such as: 49764-63-8, name is 4,5-Dibromobenzene-1,2-diamine, belongs to bromides-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 49764-63-8, Recommanded Product: 49764-63-8

Add to a pre-dried 100ml two-necked bottle, Triphenylamine 4-boronic acid (773mg),4,5-Dibromo-o-diaminobenzene (138 mg), Pd(PPh3)2Cl2 (40 mg), K2CO3 (424 mg). After nitrogen protection, 30 ml of toluene and 2 ml of deionized water were added, the temperature was raised to 80 C, and the reaction was carried out for 24 hours. After the reaction, the mixture was washed and extracted with dichloromethane and water several times. The organic phase was collected, dried over anhydrous magnesium sulfate, concentrated under reduced pressure, and then purified by column chromatography. 200-300 mesh silica gel was used as a stationary phase, and a dichloromethane / petroleum ether volume ratio 3: 1 mixture was used as a mobile phase to elute. The eluate containing the target compound was collected, and the solvent was distilled off under reduced pressure and dried. 488 mg of pink solid was obtained by thin layer chromatography with a yield of 82%.

At the same time, in my other blogs, there are other synthetic methods of this type of compound, 4,5-Dibromobenzene-1,2-diamine, and friends who are interested can also refer to it.

Reference:
Patent; Zhejiang University of Technology; Li Weijun; Xu Ning; Chen Zhangxin; Zhang Cheng; (14 pag.)CN110713493; (2020); A;,
Bromide – Wikipedia,
bromide – Wiktionary

Application of 141474-37-5,Some common heterocyclic compound, 141474-37-5, name is 2,4-Dibromo-6-fluoroaniline, molecular formula is C6H4Br2FN, 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 a 1L round bottom flask, 2,4-dibromo-6-fluoroaniline 30 g (111.56 mmol), phenylboronic acid-d5 31.2 g (245.44 mmol), potassium carbonate (K2CO3) 61.9 g (446.27 mmol), tetrakis Triphenylphosphine palladium (Pd(PPh3)4) 2.6 g (2.20 mmol), water 120 mL, toluene 300 mL and tetrahydrofuran 300 mL was added and refluxed for 24 hours. When the reaction was completed, the resultant product was layer-separated to remove the aqueous layer, the organic layer was separated and concentrated under reduced pressure, and then the solid obtained by separation by column chromatography using hexane and dichloromethane as a development solvent was dried, yielding 24.2 g. 79.4% of a white solid was obtained.

The synthetic route of 141474-37-5 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; SFC Ltd.; Lee Sang-hae; Sim So-yeong; Ryu Se-jin; (30 pag.)KR102121582; (2020); B1;,
Bromide – Wikipedia,
bromide – Wiktionary

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. 68322-84-9, name is 2-Bromo-1-fluoro-4-(trifluoromethyl)benzene, This compound has unique chemical properties. The synthetic route is as follows., Formula: C7H3BrF4

Example 63 3- {2-Ethyl-4- [3-methyl-5- (2-o-tolyloxy-4-trifluoromethyl-phenoxy)-phenoxy]-phenyl}- propionic acid Step A A mixture 3-benzyloxy-5-methyl-phenol (8.50 g, 39.7 mmol), 3-bromo-4- fluorobenzotrifluoride (9.64 g, 39.7 mmol) and 325 mesh potassium carbonate (6.58 g, 47.6 mmol) in dry DMSO (100 mL) is heated to 100 C and stirred for 8 hours under N2. The reaction is cooled and acidified with 1 N HCI. The mixture is then diluted with water and extracted with Et20. The organic layer is dried (Na2S04), and the solvent is removed in vacuo to afford crude product that is absorbed on silica gel and purified by flash chromatography using 9/1 hexanes/ethyl acetate to afford 14.14 g (81%) product. Rf = 0.52 (4/1 hexanes/EtOAc).’H NMR (400 MHz, CDCl3).

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 68322-84-9.

Reference:
Patent; ELI LILLY AND COMPANY; WO2005/37763; (2005); A1;,
Bromide – Wikipedia,
bromide – Wiktionary

Application of 19190-91-1,Some common heterocyclic compound, 19190-91-1, name is 5,6-Dibromo-1,2-dihydroacenaphthylene, molecular formula is C12H8Br2, 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: Dibromoarene 1 (0.5 mmol), alkyne 2 (0.6 mmol), Pd(OAc)2 (5 mol%, 5.6 mg ),Xantphos (5.5 mol%,16 mg), K2CO3 (1.5 mmol, 207 mg) were added into a Schlenkflask. The flask was evacuated and backfilled with nitrogen (3 cycles). Dry DMF (5mL) was added by syringe. The mixture was heated to 120 C and stirred until thereaction finished (TLC analysis). After cooling to room temperature, the mixture wasextracted three times with ethyl acetate. The organic layers were combined and driedover Na2SO4. After filtration, the solvents were evaporated. The crude product wasfurther purified by silica gel chromatography, using petroleum ether and ethyl acetateas eluents to provide the pure product

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 5,6-Dibromo-1,2-dihydroacenaphthylene, its application will become more common.

Reference:
Article; An, Wenbo; Li, Gaoqiang; Ma, Jun; Tian, Youping; Xu, Feng; Synlett; vol. 25; 11; (2014); p. 1585 – 1590;,
Bromide – Wikipedia,
bromide – Wiktionary

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 4766-33-0 as follows. Safety of 5-Bromonaphthalen-1-amine

General procedure: To a stirred solution of 3-chloro-6-nitrobenzo[d]isothiazole 1,1-dioxide (2) 1 mmol) in THF (15 mL), triethylamine (3 mmol) and aromatic amine (1 mmol) were added. The mixture was stirred at room temperature for 4~6 h. The solvent was eliminated in vacuo and the resulting residual was recrystallised from ethyl acetate/hexane to give the title compounds in mediate to high over yield.

According to the analysis of related databases, 4766-33-0, the application of this compound in the production field has become more and more popular.

Reference:
Article; Shang, Erchang; Wu, Yiran; Liu, Pei; Liu, Ying; Zhu, Wei; Deng, Xiaobing; He, Chong; He, Shan; Li, Cong; Lai, Luhua; Bioorganic and Medicinal Chemistry Letters; vol. 24; 12; (2014); p. 2764 – 2767;,
Bromide – Wikipedia,
bromide – Wiktionary