Month: September 2021

Application of 10485-09-3, 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. 10485-09-3 name is 2-Bromoindene, 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.

In a 200 mL reactor sufficiently dried and purged with argon, 0.98 g (40.3 mmol) of magnesium pieces were charged and vigorously stirred for 30 minutes while heating under reduced pressure. After cooling to room temperature, a reflux condenser was attached, and a piece of iodine and 15 mL of tetrahydrofuran were charged and stirred. A 10 mL diluted solution of 1.95 g (10.0 mmol) of 2-bromoindene is added dropwise (1.0 mL after addition, followed by heating to reflux until the color of iodine disappears with a drier, remaining after dropping of the reaction drop) It stirred at room temperature after completion | finish for 2 hours.The reaction solution is diluted with 6.00 mL (50.2 mmol) of dimethylsilyl dichloride in 10 mL of n-hexane diluted solution,The reaction was slowly added at -78 C with cooling, and stirring was continued for 19 hours while returning to room temperature.After distilling off the solvent of the reaction solution and unreacted dimethylsilyl dichloride, 20 mL of tetrahydrofuran and 1.00 mL (10.6 mmol) of 1,3-dimethyl-2-imidazolidinone were added to the residue. 2.65 g (10.0 mmol) of 7- (4-trimethylsilylphenyl) idene synthesized by the method described in WO2012 / 133717 in a fully dried, argon-substituted 100 mL reactor.15 mL of tetrahydrofuran was charged, 6.45 mL (hexane solution, 1.55 M, 10.0 mmol) of n-butyllithium solution was added, and the mixture was stirred at room temperature for 2 hours. This solution was added dropwise to the previously diluted reaction residue diluted solution cooled to -78 C., and stirring was continued for 3 hours while slowly returning to room temperature. Saturated aqueous ammonium chloride solution was added, the solubles were extracted with n-hexane, and the obtained fraction was washed with saturated brine and dried over anhydrous magnesium sulfate. After magnesium sulfate is filtered, the filtrate is evaporated and the obtained residue is purified by silica gel column chromatography to obtain the target compound represented by the following formula (A-1 L)Compound (A-1L) was obtained as an isomer mixture of 2.12 g (yield 48%).

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

Reference:
Patent; Mitsui Chemicals, Inc.; Prime Polymer Co., Ltd.; Tanaka, Yoichi; Harada, Yasuyuki; Tamura, Naoya; Hato, Ikki; Tsuchitani, Hiroko; (68 pag.)JP2019/59723; (2019); A;,
Bromide – Wikipedia,
bromide – Wiktionary

Synthetic Route of 58534-95-5,Some common heterocyclic compound, 58534-95-5, name is 3-Bromo-2-fluoroaniline, molecular formula is C6H5BrFN, 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.

The mixture of 12 (30 g), 13 (60 g), K2CO3 (91 g) and Pd(dppf)2Cl2 (19.25 g) in solvent (dioxane 400 mL, H2O 100 mL) was purged with argon in a pressure vessel for 5 min and stirred for 15 h at 100 C. The solvent was removed under reduced pressure and the remaining residue was purified by flash column chromatography. The purified material was then dissolved in MeOH and treated with HCl/MeOH. The solvent was removed and the remaining solid was washed with IPA-heptane (1/1) to afford 14.

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

Reference:
Patent; Achillion Pharmaceuticals, Inc.; Gadhachanda, Venkat Rao; Pais, Godwin; Hashimoto, Akihiro; Wang, Qiuping; Chen, Dawei; Wang, Xiangzhu; Agarwal, Atul; Deshpande, Milind; Phadke, Avinash S.; Wiles, Jason Allan; US2015/239920; (2015); 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. 937046-98-5, name is 7-Bromopyrrolo[2,1-f][1,2,4]triazin-4-amine, A new synthetic method of this compound is introduced below., Recommanded Product: 937046-98-5

To a dry, argon purged round bottom flask (100 mL) were added 7-bromo- pyrrolo[2,l-f][1,2,4]triazin-4-ylamine (234 mg, 1.10 mmol) and anhydrous THF (1 .5 mL). TMSCI (276 L, 2.2 mmol) was then added and the reaction mixture stirred for 2h. The flask was placed into a dry ice/acetone bath (- 78 C) and BuLi (2.5 mL, 4.0 mmol, 1.6 M in hexanes) was added dropwise. After 1 h, a solution of 2b (432 mg, 1.0 mmol) in THF was cooled to 0 C and then added to the reaction flask dropwise. After 1 h of stirring at -78 C, the flask was warmed to 0 C and sat. NH4CI (5 mL) was added to quench the reaction. The organics were extracted using EtOAc (3 10 mL) and the combined organic layers were dried using MgS04. The solvent was removed under reduced pressure and the crude material was purified using flash silica gel chromatography (hexanes / EtOAc). 560 mg (90 %) of the desired material 2c was isolated. LC/MS = 567.2 (M + H+). 1H NMR (300 MHz, CDC13): 5 7.85 (m, 1H), 7.27 (m, 15H), 7.01 (m, 1H), 6.51 (m, 1H), 4.66 (m, 8H), 4.40 (m, 2H), 3.79 (m, 3H), 1.62 (s,.2′-CH3 from the one anomer), 1.18 (s, 2′-CH3 from the other anomer).

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; GILEAD SCIENCES, INC.; BUTLER, Thomas; CHO, Aesop; GRAETZ, Benjamin, R.; KIM, Choung, U.; METOBO, Samuel, E.; SAUNDERS, Oliver, L.; WALTMAN, Andrew, W.; XU, Jie; ZHANG, Lijun; WO2011/35250; (2011); A1;,
Bromide – Wikipedia,
bromide – Wiktionary

Adding a certain compound to certain chemical reactions, such as: 103273-01-4, name is 2-Bromo-4-(tert-butyl)aniline, 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 103273-01-4, SDS of cas: 103273-01-4

200 mL three-necked eggplant flask fully dried (condenser, three-way cock, To a magnetic stirring bar) was added 2-methoxyphenylboronic acid (Wako Pure Chemical Industries, Ltd.) (3.19 g, 10.5 mmol), (0.05 mmol) of 2-bromo-4-tert-butylaniline (2.8 g, 10 mmol), palladium acetate (manufactured by Wako Pure Chemical Industries, Ltd.), 2-dicyclohexylphosphino-2′,6-dimethoxybiphenyl (Manufactured by Sigma-Aldrich Japan Co., Ltd.) (0.041 g, 0.1 mmol) 6.9 g (30 mmol) of potassium phosphate monohydrate (manufactured by Wako Pure Chemical Industries, Ltd.) In addition, suspended in 20 mL of toluene (manufactured by Kanto Chemical Co., Ltd.) The reaction was carried out at 100 C. for 3 hours. To this reaction solution was added 50 mL of water, After extraction with toluene, the organic layer was dried with MgSO 4 (manufactured by Kanto Kagaku Co., Ltd.) The solvent was distilled off under reduced pressure to obtain a crude product. The crude product was purified by silica gel column chromatography (eluent; hexane (Manufactured by KANTO CHEMICAL CO., LTD.) / Ethyl acetate (manufactured by KANTO CHEMICAL CO., LTD.) = 9/1) to obtain 2.40 g (94%, light yellow liquid) of Compound

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-Bromo-4-(tert-butyl)aniline, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; Mitsui Chemicals Co., Ltd.; Kinoshita, Shinsuke; Kawamura, Kazumori; Ishii, Seiichi; Tanaka, Kenichi; Hanada, shiori; Saito, Yasunori; Hara, Retsu; Mizobuchi, Yusuke; Muroto, Toshihiro; (55 pag.)JP5769443; (2015); B2;,
Bromide – Wikipedia,
bromide – Wiktionary

These common heterocyclic compound, 1647-26-3, name is 1-Bromo-2-cyclohexylethane, 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. Quality Control of 1-Bromo-2-cyclohexylethane

To a solution of 1.22 g of 2-cyclohexylethyl bromide and 1.56 g ethyl N-[7-chloro-3-[2,3-O-(1-methylethylidene)-5-O-(2H-tetrahydropyran-2-yl)-beta-D-ribofuranosyl]-3H-imidazo[4,5-b]-pyridin-5-yl]-carbamate in 15 ml of dry dimethylformamide is added 0.25 g of sodium hydride (60% dispersion in mineral oil). After a few minutes the gas evolution subsides and the mixture is heated to 70 for 20 minutes. The reaction is quenched with water, and extracted three times with ethyl acetate. The organic extract is washed with water and dried (sodium sulfate). Evaporation of the solvent in vacuo gives an oil which is purified by flash chromatography on silica gel (40% ether/hexane followed by ether) to give ethyl N-[7-chloro-3-[2,3-O-(1-methylethylidene)-5-O-(2H-tetrahydropyran-2-yl)-beta-D-ribofuranosyl]-3H-imidazo[4,5-b]pyridin-5-yl]-N-(2-cyclohexylethyl)-carbamate.

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

Reference:
Patent; Ciba-Geigy Corporation; US4977144; (1990); A;,
Bromide – Wikipedia,
bromide – Wiktionary

Adding a certain compound to certain chemical reactions, such as: 7766-50-9, name is 11-Bromo-1-undecene, 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 7766-50-9, Recommanded Product: 7766-50-9

To a solution of 11-Bromoundec-1-ene (2.2 mL, 10.1 mmol) in dry DMF (100 mL) was added 0.75 g (10.1 mmol) of NaN3. The solution was stirred for 12 h at room temperature. The reaction mixture was poured into 20 mL water and extracted with ethyl acetate (2 x 30 mL). The combined organic layer was washed with saturated NaCl solution and dried over anhydrous Na2SO4. Solvent was removed under reduced pressure to obtain the product as yellow oil. The product was used for the next step without any further purification. Yield: 1.9 g (96 %).Rf: 0.96 (1:9 Ethyl acetate & Cyclohexane).1H-NMR (CDCl3, 300 MHz, ppm): delta = 1.30 (s, 12H), 1.60 (m, 2H), 2.05 (m, 2H), 3.26 (t, J = 7.0 Hz, 2H), 4.96 (m, 2H), 5.83 (m, 1H). 13C-NMR (CDCl3, 75 MHz, ppm): delta = 26.9, 29.0, 29.1, 29.3, 29.3, 29.5, 29.6, 34.0, 51.7, 114.3, 139.3.

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, 11-Bromo-1-undecene, other downstream synthetic routes, hurry up and to see.

Reference:
Article; Bhabak, Krishna P.; Proksch, Denny; Redmer, Susanne; Arenz, Christoph; Bioorganic and Medicinal Chemistry; vol. 20; 20; (2012); p. 6154 – 6161;,
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. 28342-75-8, name is 1,5-Dibromo-2,4-difluorobenzene, A new synthetic method of this compound is introduced below., HPLC of Formula: C6H2Br2F2

A 1.6 M solution of butyl lithium in hexane (114 mL, 182 mmol) is added to a -78 C. solution of 1,5-dibromo-2,4-difluorobenzene (41.3 g, 152 mmol) in diethyl ether (290 mL). Dimethylformamide (14.4 g, 198 mmol) is added and the reaction is stirred at -78 C. for 15 minutes. The reaction is quenched with 1 N HCl (300 mL), is diluted with water, and extracted three times with ethyl acetate. The organic layer is dried over sodium sulfate and the solvent is removed under reduced pressure to give crude material that is purified by silica gel chromatography with a linear gradient of 0% to 50% CH2Cl2 in hexanes over 30 minutes to give the title compound (20.51 g, 61%). GC-MS m/e (79Br/81Br) 220, 222

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; ELI LILLY AND COMPANY; US2011/9395; (2011); 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. 1647-26-3, name is 1-Bromo-2-cyclohexylethane, A new synthetic method of this compound is introduced below., SDS of cas: 1647-26-3

solution of tert-butyl {6-[({[(Z)-(4-methyl-5-oxo-4,5-dihydro-1 ,2,4-oxadiazol-3- yl)(phenyl)methylene]amino}oxy)methyl]pyridin-2-yl}carbamate (100 mg, 0.235 mmol, 1 eq.) in A/,/V-dimethylformamide (2 ml) was treated with sodium hydride (10 mg, 0.259 mmol, 1.1 eq.) and stirred at room temperature for 30 minutes. (2-Bromoethyl)cyclohexane (67 mg, 0.353 mmol, 1.5 eq.) was then added and stirring was allowed overnight. The reaction was quenched by addition of water and extracted with EtOAc (3 x 20 ml). The organics were combined, washed with aq. sat. NaCI. dried over gSO and concentrated to afford tert-butyl (2- cyclohexylethyl ){6-[({[(Z)-(4-methyl-5-oxo-4 , 5-d i hyd ro- 1 ,2 ,4-oxad iazol-3- yl)(phenyl)methylene]amino}oxy)methyl]pyridin-2-yl}carbamate (108 mg, 86% yield) which was used in the next step without further purification.

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; BAYER INTELLECTUAL PROPERTY GmbH; BRAUN, Christoph; SAWADA, Haruko; LACHAISE, Helene; BRUNET, Stephane; RINOLFI, Philippe; DUBOST, Christophe; COQUERON, Pierre-Yves; MAECHLING, Simon; REBSTOCK, Anne-Sophie; WACHENDORFF-NEUMANN, Ulrike; WO2013/37717; (2013); A1;,
Bromide – Wikipedia,
bromide – Wiktionary

Synthetic Route of 21524-34-5,Some common heterocyclic compound, 21524-34-5, name is 2-Bromo-1,3,5-triisopropylbenzene, molecular formula is C15H23Br, 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.

To a 50 mL oven-dried flask was added 2-bromo-1,3,5-triisopropylbenzene (10.14 g, 0.036 mol, 1.0 equiv.), phenyl boronic acid (7.32 g, 0.06 mol, 1.6 equiv.), K3PO4 (17.0 g, 0.80 mol, 2.2 equiv), Pd2(dba)3 (0.366 g, 0.4 mmol) and SPhos (0.328 g, 0.8 mmol). The flask was evacuated and back-filled with argon three times prior to 40 mL of dry THF and 40 mL of dry toluene was added via syringe. The mixture was then stirred and heated in a 100 C. oil bath for 16 hr. Upon reaction completion, as determined by GC-MS, the mixture was filtered through silica and washed with EtOAc. The filtrate was collected and the solvent was removed under vacuum. The crude residue was purified by flash chromatography on silica gel using an EtOAc/hexanes mixture (0 to 10% EtOAc) as the eluent to get a white solid (9 g, 90%). 1H NMR (600 MHz, Chloroform-d) delta 7.42 (dd, J=8.1, 6.8 Hz, 2H), 7.39-7.34 (m, 1H), 7.23-7.19 (m, 2H), 7.09 (s, 1H), 2.97 (p, J=7.0 Hz, 1H), 2.62 (ddd, J=12.7, 7.7, 6.4 Hz, 2H), 1.34 (dd, J=7.0, 0.9 Hz, 5H), 1.11 (dd, J=6.9, 0.9 Hz, 11H) ppm. 13C NMR (151 MHz, CDCl3) delta 147.82, 146.51, 140.84, 137.08, 129.80, 127.91, 126.40, 120.53, 77.26, 77.05, 76.84, 34.28, 30.28, 24.25, 24.13 ppm

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 2-Bromo-1,3,5-triisopropylbenzene, its application will become more common.

Reference:
Patent; Agency for Science, Technology and Research; Johannes, Charles W.; Robins, Edward G.; Jong, Howard; Lim, Yee Hwee; Chia, Saei Weng; Yang, Yong; Podichetty, Anil; (84 pag.)US2016/207034; (2016); A1;,
Bromide – Wikipedia,
bromide – Wiktionary

Related Products of 114078-88-5,Some common heterocyclic compound, 114078-88-5, name is 5-Bromo-1,2,3-triazine, molecular formula is C3H2BrN3, 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.

Using the most conditional verification experiment, the reaction steps are: in a 10mL dry sealed reaction tube, add 5-bromo-1,2,3-triazine 1a (15.9mg, 0.10mmol), DBN (37.3 mg, 0.30 mmol) and diethyl cyanomethyl phosphate 1b (35.4 mg, 0.20 mmol). After nitrogen substitution three times, the solvent 1,4-dioxane (1.0 mL) was added, and the sealed reaction tube was placed at 70 C to react. The reaction was monitored by TLC. After the reaction was completed, it was extracted with dichloromethane (3 * 10mL). The organic phase was dried over anhydrous sodium sulfate and concentrated in vacuo. After column chromatography, the target product 1c (24.6mg) was obtained. 80%.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 5-Bromo-1,2,3-triazine, its application will become more common.

Reference:
Patent; Chongqing University; Li Baosheng; Luo Han; Zhang Yuan; An Jiaoyu; Xu Mingchuan; Lu Qixing; Tang Zongyuan; Li Shanshan; (16 pag.)CN111004284; (2020); A;,
Bromide – Wikipedia,
bromide – Wiktionary