Month: June 2021

These common heterocyclic compound, 67567-26-4, name is 4-Bromo-2,6-difluoroaniline, 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. name: 4-Bromo-2,6-difluoroaniline

Example 16B V,jV-dibenzyl-4-bromo-2,6-difluorobenzenamineA mixture of the product of Example 16A (1.1 g, 5.3 mmol), benzyl bromide (949 mg, 0.66 ml) and potassium bicarbonate (1.46 mg, 10.6 mmol) in NN-dimethylformamide (3 itiL) was stirred at ambient temperature until TLC indicated no starting material remained. Ethyl acetate was added, and the mixture was washed with water and brine and dried over anhydrous sodium sulfate. After filtration and concentration, the residue was purified by flash chromatography on silica gel (200-300 mesh) eluting with 10/1 petroleumether/dichoromethane to give the title compound.

The synthetic route of 4-Bromo-2,6-difluoroaniline has been constantly updated, and we look forward to future research findings.

Reference:
Patent; ABBOTT LABORATORIES; ABBOTT LABORATORIES TRADING (SHANGHAI) COMPANY, LTD.; VASUDEVAN, Anil; PENNING, Thomas Dale; CHEN, Huanming; LIANG, Bo; WANG, Shaohui; WU, Fengchun; SHEN, Yan; LIU, Cuihua; ZOU, Zhenguang; WO2012/97684; (2012); A1;,
Bromide – Wikipedia,
bromide – Wiktionary

Electric Literature of 134168-97-1, These common heterocyclic compound, 134168-97-1, name is 3-Bromo-5-fluoroaniline, 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.

Intermediate S1: N-(3-bromo-5-fluorophenyl)methanesulfonamide A solution of commercially available 3-bromo-5-fluoroaniline (0.500 g, 2.64 mmol) in pyridine (9.4 mL) was cooled to 0 C. and methanesulfonyl chloride (0.265 mL, 3.43 mmol) was added drop-wise; the resulting solution was allowed to warm to room temperature and stirred for 2 h. The solvent was removed under reduced pressure and the crude was partitioned between EtOAc and aqueous 1N HCl. The organic phase was dried over sodium sulfate and the solvent was removed; the crude was purified by flash chromatography on Biotage silica gel SNAP cartridge (cyclohexane to cyclohexane_EtOAc=50:50) to afford title compound as a white solid (0.543 g, 2.03 mmol, 77% yield). MS/ESI+ not detectable [MH]+, Rt=0.91 min (Method A). 1H NMR (400 MHz, DMSO-d6) delta ppm 10.29 (s, 1H), 7.23-7.30 (m, 1H), 7.19 (s, 1H), 6.99-7.06 (m, 1H), 3.12 (s, 3H).

Statistics shows that 3-Bromo-5-fluoroaniline is playing an increasingly important role. we look forward to future research findings about 134168-97-1.

Reference:
Patent; CHIESI FARMACEUTICI S.P.A.; BIAGETTI, Matteo; ACCETTA, Alessandro; CAPELLI, Anna Maria; GUALA, Matilde; RETINI, Michele; US2015/361100; (2015); A1;,
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. 348-57-2, name is 1-Bromo-2,4-difluorobenzene, This compound has unique chemical properties. The synthetic route is as follows., name: 1-Bromo-2,4-difluorobenzene

Iron powder (16.49 g, 291 mmol) is added to 1-bromo-2,4-difluorobenzene (110 mL, 968 mmol) in 1,2-dichloroethane (968 mL) in a 3-neck flask at ambient temperature under a stream of nitrogen. A solution of bromine (59.7 mL, 1.16 mol) in 1,2-dichloroethane (968 mL) is added dropwise over 1 hour and the reaction mixture is stirred at ambient temperature for 18 h. The reaction mixture is cooled to 0 C. and a saturated aqueous solution of sodium bisulfate (1.11 L, 533 mmol) is added portionwise and the mixture is separated. The aqueous phase is extracted with dichloromethane. The organic layer is washed with a saturated aqueous solution of sodium bicarbonate, water, and brine. The organic layer is dried over sodium sulfate, and the solvent is removed under reduced pressure to give a residue purified with a pad of silica using diethyl ether to give the title compound (229 g, 76%). 1H NMR (400 MHz, CDCl3) delta 7.70 (dd, J=4.6, 6.8 Hz, 1H), 6.95-6.92 (m, 1H).

According to the analysis of related databases, 348-57-2, the application of this compound in the production field has become more and more popular.

Reference:
Patent; ELI LILLY AND COMPANY; US2011/9395; (2011); A1;,
Bromide – Wikipedia,
bromide – Wiktionary

Related Products of 7051-34-5, 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. 7051-34-5 name is (Bromomethyl)cyclopropane, 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.

Reference Example 1-19; 2-(cyclopropylmethyO-l,3-dithiane-2-carboxylic acid ethyl esterSodium hydride (1.03 g) was suspended in toluene (40.0 mL), followed by adding a solution of ethyl l,3-dithiane-2-carboxylate (4.13 g) and (bromomethyl)cyclopropane (2.52 mL) in dimethylformamide (10 mL) to the suspension at 00C and stirring the mixture overnight at room temperature. A saturated aqueous ammonium chloride solution was added to the reaction solution, and the mixture was extracted with ethyl acetate. The organic layer was washed with a saturated saline solution and then dried over anhydrous sodium sulfate. Insoluble matters were filtered out, and the filtrate was concentrated under reduced pressure to give the title compound (5.20 g) as a colorless oil. mass:247(M+l)+ .

At the same time, in my other blogs, there are other synthetic methods of this type of compound, (Bromomethyl)cyclopropane, and friends who are interested can also refer to it.

Reference:
Patent; BANYU PHARMACEUTICAL CO.,LTD.; KAMEDA, Minoru; KOBAYASHI, Kensuke; NAKAMA, Chisato; ANDO, Makoto; SATO, Nagaaki; WO2010/126163; (2010); A1;,
Bromide – Wikipedia,
bromide – Wiktionary

Some common heterocyclic compound, 65896-11-9, name is 2-Bromo-6-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. Application In Synthesis of 2-Bromo-6-fluoroaniline

At 15 deg.C, 2-bromo-6-fluoroaniline (1.00 g, 5.26 mmol) and dimethylphosphine oxide (451.84 mg, 5.79 mmol) in water (20ml) mixture was added potassium carbonate ( 2.91 g, 21.05 mmol) and Pd / C (150 mg). The reaction mixture was stirred at 160 deg.C microwave heating for 3 hours. TLC (petroleum ether: ethyl acetate = 10: 1) showed the reaction was complete. The reaction mixture (20mL × 4) and extracted with dichloromethane. The combined organic layer was filtered, the filtrate was concentrated and purified by column chromatography (dichloromethane: methanol = 1: 0-10: 1) afforded the title compound (100mg, yield 10.16%) as a yellow solid.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 65896-11-9, its application will become more common.

Reference:
Patent; Nanjing Mingde New Drug Research and Development Co. Ltd.; Qilu Pharmaceutical Co., Ltd.; Ding, Zhaozhong; Zhang, Minghui; Chen, Shuhui; Liu, Xile; Zhu, Yidong; Fan, Chuanwen; Zhao, Baoping; Zhang, Long; Chen, Dong; Yang, Yingying; Zheng, Qingmei; Zheng, Shansong; Wan, Haiwen; Hu, Jinqing; (93 pag.)CN105330698; (2016); A;,
Bromide – Wikipedia,
bromide – Wiktionary

Application of 58971-11-2, 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. 58971-11-2, name is 3-Bromophenethylamine, This compound has unique chemical properties. The synthetic route is as follows.

4i was then obtained by following the general procedure. A solution of compound 3 (140 mg, 0.7 mmol) in n-BuOH (6 mL) was treated with DIEA (98.6 mg, 0.77 mmol) and 3-bromophenethylamine (154 mg, 0.77 mmol). Compound 4i was purified from this crude material by column chromatography (silicagel, n-hexane/EtOAc=3:1) (128.2 mg, 50.7%). 1H-NMR (400 MHz, CDCl3) delta 7.71-762 (m, 2H), 7.49 (d, J=8.4 Hz, 1H), 7.38-7.30 (m, 2H), 7.14-7.08 (m, 1H), 5.99 (s, 1H, -NH), 3.86 (dd, J=12.4, 6.8 Hz, 2H, -CH2-), 2.94 (t, J=7.2 Hz, 2H, -CH2-). 13C-NMR (100 MHz, CDCl3) delta 159.8, 156.7, 149.8, 147.2, 140.9, 139.9, 132.6, 130.9, 129.3, 128.9, 126.5, 125.3, 121.8, 119.6, 112.2, 41.3, 33.7. LC-MS (ESI) m/z: 362.0 ([M+H]+);

The chemical industry reduces the impact on the environment during synthesis 3-Bromophenethylamine. I believe this compound will play a more active role in future production and life.

Reference:
Patent; The Board of Regents of the University of Oklahoma; Wang, Weidong; Lee, Jae Wook; (35 pag.)US2019/47988; (2019); A1;,
Bromide – Wikipedia,
bromide – Wiktionary

Some common heterocyclic compound, 1003-99-2, name is 2-Bromo-5-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. Application In Synthesis of 2-Bromo-5-fluoroaniline

2-Bromo-5- fluorobenzenamine (15 g, 78.94 mmol) was weighed into a 100 mL flask and dissolved in 100 mL of 6N HCl. The reaction mixture was heated to reflux, followed by dropwise addition of (E)-but-2-enal (6.87 ml, 83 mmol) mixed with 1.0 mL deionized water over 25 minutes. Following complete addition, the reaction was heated at 100 °C for an additional 35 minutes. The reaction was cooled to ambient temperature, followed by addition of 50 mL of Et2O. The reaction was stirred for 5 minutes followed by removal of Et2O by separatory funnel. ZnCl2 (3.587 g, 26 mmol) was added to the aqueous layer in two portions and the reaction mixture was cooled to 0 0C over 30 minutes. The aqueous layer was then taken to pH 8.0 using concentrated NH4OH. The aqueous layer was then extracted with Et2O and then EtOAc. The combined organic phases were dried over Na2SO4, filtered and concentrated in vacuo, affording the desired product 8-bromo-5-fluoro-2-methylquinoline (18.1 g, 95 percent yield) as a solid.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 1003-99-2, its application will become more common.

Reference:
Patent; ARRAY BIOPHARMA INC.; WO2008/121687; (2008); A2;,
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. 53078-85-6, name is 2-Bromo-5-methylaniline, This compound has unique chemical properties. The synthetic route is as follows., SDS of cas: 53078-85-6

The corresponding imidazopyridine (0.2 mmol) was added sequentially to a 25 ml Schlenk tube filled with oxygen and equipped with a magnetic stirrer at room temperature.Cuprous chloride (0.02 mmol), 2-bromo-5-methylaniline (0.2 mmol),1,10-azaphenanthroline (0.04 mmol), sodium carbonate (0.4 mmol), adding carbon disulfide (0.2 mmol), DMSO (2.0 mL) with a syringe under oxygen, and placing the reaction tube in a 110 C oil bath with stirring 6 hour. The obtained solution was cooled to room temperature, 2 mL of deionized water was added to the reaction liquid, and the mixture was uniformly mixed. Each time, 3 mL of ethyl acetate was used as an extracting agent, and the crude product was extracted from the reaction liquid by a liquid separation extraction operation, and the extract was combined. The solvent was removed by a rotary evaporator; the residue was purified on a silica gel column (yield: 200 mesh to 300 mesh, eluent petroleum ether / ethyl acetate (7:1 v/v)) to give the desired product 61.0 mg. The yield was 76%.

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 53078-85-6.

Reference:
Patent; Qingdao University of Science and Technology; Yang Daoshan; Yan Qiuli; (17 pag.)CN110294757; (2019); A;,
Bromide – Wikipedia,
bromide – Wiktionary

Application of 10485-09-3, 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. 10485-09-3, name is 2-Bromoindene, This compound has unique chemical properties. The synthetic route is as follows.

General procedure: An oven-dried 10 mL reaction vial equipped with a stir bar was charged with azole heterocycles (1, 0.2 mmol, 1.0 equiv) and alkenyl bromides (2, 0.30 mmol, 1.5 equiv) in a glove box under a nitrogen atmosphere. A solution of catalytic Pd2(dba)3 (9.15 mg, 0.01 mmol, 5 mol%) and NiXantphos (11.03 mg, 0.02 mmol, 10 mol%) was stirred in 1 mL of dry tetrahydrofuran (THF) for 2 h at room temperature. Then, t-BuONa (57.7 mg, 0.6 mmol, 3.0 equiv) and reagent mixed with catalyst were added to the reaction mixture. And thenthe vial was capped. According to the temperature requirements for different products, some vials were stirred in the glove box for 24 h, but others were removed from the glove box, and stirred for 24 h at 70 or 150 . The reaction mixture was quenched with three drops of H2O, diluted with 3 mL of ethyl acetate, and filtered over a pad of silica. The pad was rinsed with ethyl acetate (15-25 mL), and the combined solutions were concentrated in vacuo. The crude material was loaded onto a deactivated silica gel column and purified by flash chromatography to afford the desired product.

The chemical industry reduces the impact on the environment during synthesis 2-Bromoindene. I believe this compound will play a more active role in future production and life.

Reference:
Article; Yao, Yun-Xin; Fang, Dong-Mei; Gao, Feng; Liang, Xiao-Xia; Tetrahedron Letters; vol. 60; 1; (2019); p. 68 – 71;,
Bromide – Wikipedia,
bromide – Wiktionary