Tag: M.W=200-300

These common heterocyclic compound, 5003-71-4, name is 3-Bromopropan-1-amine hydrobromide, 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. 5003-71-4

Tert-butyl n-(3-bromopropyl)carbamate: Prepared from 3-bromopropylamine hydrobromide and BOC2O in the presence of base in dichloromethane, 9.89 mmol: 1H NMR (CDCl3) delta 5.07 (br, 1H), 3.31 (t, 2H, J=6.6 Hz), 3.12 (apparent br q, 2H, J=6.0 Hz), 1.92 (p, 2H, J=6.6 Hz), 1.30 (s, 9H).

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 5003-71-4.

Reference:
Patent; Borowsky, Beth; Blackburn, Thomas P.; Ogozalek, Kristine; US2003/82623; (2003); A1;,
Bromide – Wikipedia,
bromide – Wiktionary

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. 67567-26-4 name is 4-Bromo-2,6-difluoroaniline, 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. 67567-26-4

The compound of formula XIV-1 (31.05 g, 0.15 mol), the compound of formula XIII-1 (30.3 g, 0.30 mmol)Phosphorus oxychloride(20.9 mL, 0.225 mol) were added sequentially to anhydrous toluene. Triethylamine (31.3 mL, 0.225 mol) was added in an ice bathConstant pressure funnel slowly added dropwise to the reaction flask,Maintain the internal temperature is less than 60 .The reaction flask was transferred to an oil bath and heated to reflux.After 2 hours, the reaction flask was cooled to room temperature, slowly poured into 300 g of ice water mixture, 300 ml of ethyl acetate was added, sufficientAfter the mixture was separated, the aqueous layer was extracted with 200 ml of ethyl acetate again. The combined organic layers were washed with saturated brine and dried over anhydrous sulfuric acidSodium dried, concentrated under reduced pressure to give a pale yellow solid, beaten with 100 ml of petroleum ether for 10 minutes, filtered under reduced pressure to give a compound of formulaCompound XV-1 (28.0 g) as an off white solid (yield 92.3%)

At the same time, in my other blogs, there are other synthetic methods of this type of compound, 4-Bromo-2,6-difluoroaniline, and friends who are interested can also refer to it.

Reference:
Patent; Zhengda Tianqing Pharmaceutical Group Co., Ltd.; Zhang Yinsheng; Liu Yingshuai; Qin Hui; Li Yuan; Zhao Kaidi; Miao Lei; Hu Jie; Liu Haiyan; Wang Xiaojin; (33 pag.)CN107266421; (2017); A;,
Bromide – Wikipedia,
bromide – Wiktionary

A common compound: 49764-63-8, name is 4,5-Dibromobenzene-1,2-diamine, belongs to bromides-buliding-blocks compound, it can change the direction of chemical reaction, and react with certain compounds to generate new functional products. A new synthetic method of this compound is introduced below. 49764-63-8

6,7-Dibromo-1,4-dihydroquinoxaline-2,3-dione. A mixture of 4,5-dibromo-1,2-phenylenediamine (1.862 g, 7.0 mmol) and oxalic acid dihydrate (1.06 g, 8.4 mmol) in 2N HCl (100 mL) was heated at 125 C. for 2 h then allowed to cool to 25 C. The solid was collected by vacuum filtration, washed with water and dried at 40 C. under 1 mmHg for 10 h affording 2.053 g (92%) of the title compound as a light brown powder. 1 H NMR (DMSO-d6) 11.995 (s, 2H), 7.361 (s, 2H).

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, 49764-63-8, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; The State of Oregon, acting by and through The Oregon State Board of Higher Education, acting for and on behalf of The Oregon Health Sciences University; The University of Oregon; The Regents of the University of California; US5514680; (1996); A;,
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. 51554-93-9, name is 1-Bromo-4-octylbenzene belongs to bromides-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below. 51554-93-9

Under nitrogen atmosphere, 10 ml of a solution of 1.6M n-butyl lithium (16 mmol) in hexane is put into a 100 ml three-necked flask cooled at -80 C. After cooling to -80 C., 10 ml of THF is added dropwise thereto using a dropping funnel while the THF is maintained at -60 C. Thereafter, 3.1 g (16 mmol) of 1-bromo-4-n-octylbenzene maintained at -60 C. is added dropwise thereto using a dropping funnel. The resultant mixture is stirred at -40 C. for 1 hour, and a solution of 2.3 g (22 mmol) of trimethyl borate in 10 ml of THF is added dropwise to the mixture using a dropping funnel while the temperature of the added solution is maintained at -40 C. Thereafter, the temperature of the mixture is gradually increased to 10 C. over 2 hours, and 50 ml of a 10% HCl aqueous solution is added thereto at 0 C., and extraction is performed using 100 ml of toluene. The extract is washed with 100 ml of pure water three times, and is dehydrated using sodium sulfate. Toluene is distilled off by reducing the pressure, whereby remaining matter in an amount of 3.3 g is obtained. The remaining matter is washed with a mixed solution of 100 ml pure water/100 ml hexane, whereby 2.0 g of Compound V-a, which is 4-n-octylphenyl borate, is obtained. The obtained compound is identified as the desired product by 1H-NMR and IR.

The synthetic route of 51554-93-9 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; FUJI XEROX CO., LTD.; US2010/137611; (2010); A1;,
Bromide – Wikipedia,
bromide – Wiktionary

86845-27-4,Some common heterocyclic compound, 86845-27-4, name is 5-Bromo-2-methylbenzotrifluoride, molecular formula is C8H6BrF3, 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.

Compounds 2 to 12 can be prepared in analogy to compound 1.In the case of compound 1 1 , the required intermediate for step a) was synthesised as follows: To a stirred solution of 4-bromo-1-methyl-2-trifluoromethylbenzene (10 g) in tetrachloromethane (100 ml) at room temperature is added N-bromosuccinimide (7.5 g) and azobisisobutyronitrile (700 mg). After 15 h of stirring at reflux, the reaction is allowed to cool to room temperature, water is added and the reaction mixture is extracted twice with ethyl acetate. The organic layer is washed with water, dried over magnesium sulfate and concentrated in vacuo. The residue is purified by flash chromatography (9:1cyclohexane: ethyl acetate) to yield 4-bromo-1-bromomethyl-2-trifluoromethylbenzene (7.1 g).

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-2-methylbenzotrifluoride, its application will become more common.

Reference:
Patent; BOEHRINGER INGELHEIM INTERNATIONAL GMBH; MARTYRES, Domnic; ANDERSKEWITZ, Ralf; HOENKE, Christoph; KRIEGL, Jan; OOST, Thorsten; RIST, Wolfgang; SEITHER, Peter; WO2012/130633; (2012); A1;,
Bromide – Wikipedia,
bromide – Wiktionary

327-51-5, The chemical industry reduces the impact on the environment during synthesis 327-51-5, name is 1,4-Dibromo-2,5-difluorobenzene, I believe this compound will play a more active role in future production and life.

Example 9 Synthesis of Compound 31 In a 1,000-mL three-necked flask were placed 8.0 g (27.8 millimoles) of 2-carbazolylphenylboronic acid, 4.0 g (12.8 millimoles) of 1,4-dibromo-2,5-difluorobenzene, and 1.6 g (1.4 millimoles) of tetrakis(triphenylphosphine)palladium(0), then 75 mL of ethanol and 150 mL of toluene were added, and the mixture was stirred. Thereafter, a solution of 14.3 g (135.0 millimoles) of sodium carbonate in 150 mL of water was thrown into the flask. The mixture was then heated to 80C and stirred for 17 hours. The reaction solution was cooled to room temperature, transferred to a 1,000-mL separatory funnel, and separated into an organic layer and an aqueous layer. The organic layer was washed three times with 200 mL of water and then dehydrated over magnesium sulfate, the magnesium sulfate was filtered off, and the solvent was distilled off under reduced pressure. The reaction mixture thus obtained was purified by recrystallization from THF and methanol to yield 5.1 g of Compound 31 as a white solid; EI-MS, 597 (M+1); melting point, 263C; glass transition temperature, 92C.

The chemical industry reduces the impact on the environment during synthesis 1,4-Dibromo-2,5-difluorobenzene. I believe this compound will play a more active role in future production and life.

Reference:
Patent; Nippon Steel Chemical Co., Ltd.; EP2272828; (2011); A1;,
Bromide – Wikipedia,
bromide – Wiktionary

The chemical industry reduces the impact on the environment during synthesis 3638-73-1, name is 2,5-Dibromoaniline, I believe this compound will play a more active role in future production and life. 3638-73-1

3.1) In a 5 L three-necked flask, 836 g of compound III, 1500 mL of ethyl acetate and 900 mL of acetic anhydride were added and stirred for 10 min to obtain a mixture E; 3.2) Add 400 mL of triethylamine to vessel C where mixture E is located. Reflux at 70 C for 2 h to obtain a mixture F; 3.3) After filtering the mixture F, washing with ice ethanol, adjusting the pH to 8-10 with sodium hydroxide solution, and performing an ice bath; 3.4) The product precipitated after the ice bath in step 3.3) is filtered and washed with ice ethanol. Obtaining 2-acetamido-p-dibromobenzene, ie, compound 897.98 g (yield 92%);

The chemical industry reduces the impact on the environment during synthesis 3638-73-1. I believe this compound will play a more active role in future production and life.

Reference:
Bromide – Wikipedia,
bromide – Wiktionary

28342-75-8,Some common heterocyclic compound, 28342-75-8, name is 1,5-Dibromo-2,4-difluorobenzene, molecular formula is C6H2Br2F2, 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 mixture of 2-(2-methoxy-1-naphthalenyl)-boronic acid (3.24 g, 16 mmole), 1,5-dibromo-2,4-difluorobenzene (1.78 g, 6.55 mmole), Pd(PPh3)4 (0.33 g, 0.29 mmole) and potassium carbonate (4.53 g, 32.8 mmole) in 1,2-dimethoxyethane (120 ml) and water (30 ml) was stirred with heating at reflux temperature under nitrogen atmosphere for 4 hours. After that reaction mixture cooled down, precipitate collected by filtration to give 1.12 g of the product. Organic phase of the filtrate was evaporated further and the second precipitate collected by filtration, dried in vacuum to give 1.8 g of the product. Crude product as a mixture of diastereomers was used for the next step without further purification. Crude product can be purified by chromatography on silica gel column using gradient elution with mixtures of hexanes and dichlromethane to isolate pure isolated diastereomers. MS: MH+ = 427.1H-NMR of diastereomer 1 (CDCl3, 500 MHz): 3.95 (s, 6H), 7.14 (t, 1H, J = 9 Hz), 7.34-7.37 (m, 3H), 7.38 (d, 2H, J = 9 Hz), 7.43 (td, 2H, J1 = 1 Hz, J2 = 8 Hz), 7.68 (d, 2H, J = 9 Hz), 7.83 (d, 2H, J = 8 Hz), 7.92 (d , 2H, J = 9 Hz).1H-NMR of diastereomer 2 (CDCl3, 500 MHz): 3.91 (s, 6H), 7.14 (t, 1H, J = 9 Hz), 7.31-7.38 (m, 3H), 7.38 (d, 2H, J = 9 Hz), 7.44 (td, 2H, J1 = 1 Hz, J2 = 8 Hz), 7.64 (d, 2H, J = 9 Hz), 7.83 (d, 2H, J = 9 Hz), 7.92 (d, 2H, J = 9 Hz).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 28342-75-8, its application will become more common.

Reference:
Patent; E. I. DU PONT DE NEMOURS AND COMPANY; SKULASON, Hjalti; DIEV, Viacheslav V.; VO, Giang Dong; GAO, Weiying; WU, Weishi; HERRON, Norman; HOWARD, Michael Henry, Jr.; DOGRA, Kalindi; ZOU, Yunlong; (195 pag.)WO2018/97937; (2018); A1;,
Bromide – Wikipedia,
bromide – Wiktionary

Adding some certain compound to certain chemical reactions, such as: 3972-65-4, name is 1-Bromo-4-(tert-butyl)benzene, 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 3972-65-4. 3972-65-4

General procedure: An oven-dried 10 mL reaction vial equipped with a stir bar was charged with Pd(OAc)2 (1.12mg, 0.005 mmol) and 3a (2.7 mg, 0.0075 mmol) under a nitrogen atmosphere, and 0.5 mL of dry toluene was added to the mixture. After stirring for 5 min at room temperature, NaN(SiMe3)2 (55 mg, 0.3 mmol, 3 equiv) was added to the reaction vial. After stirring for another 15 min at room temperature, 4-benzylpyridine (20.3 mg, 0.12 mmol, 1.2 equiv) was added to the reaction mixture followed by 1-bromo-4-tert-butylbenzene (21.3 mg, 0.1 mmol, 1 equiv). The reaction mixture was stirred for 16 h at 60 C, quenched with two drops of H2O, diluted with 3 mL of ethyl acetate, and filtered over a pad of MgSO4 and silica. The pad was rinsed with additional ethyl acetate, and the solution was concentrated in vacuo. The crude material was loaded onto a silica gel column and purified by flash 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 1-Bromo-4-(tert-butyl)benzene.

Reference:
Article; Zhou, Bi-Hui; Wu, Chen; Chen, Xing-Xiu; Huang, Hong-Xia; Li, Lin-Lin; Fan, Li-Mei; Li, Jie; Tetrahedron Letters; vol. 58; 44; (2017); p. 4157 – 4161;,
Bromide – Wikipedia,
bromide – Wiktionary

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. 58971-11-2 name is 3-Bromophenethylamine, 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. 58971-11-2

A solution of 2- (3-bromophenyl) ethylamine (2 g, 10 mmol)Was dissolved in dichloromethane (30 mL)To this was added triethylamine (3 mL, 20.99 mmol) andAcetic anhydride (2 mL, 20.99 mmol).The reaction mixture was stirred at room temperature overnight, followed by water (50 mLx3), brine (50 mL x 3), dried over anhydrous sodium sulfate, filtered and concentrated under reduced pressure to give the crude product (2.42 g, 100%).

At the same time, in my other blogs, there are other synthetic methods of this type of compound, 3-Bromophenethylamine, and friends who are interested can also refer to it.

Reference:
Patent; Guangdong Dongyangguang Pharmaceutical Co., Ltd.; Jiatuo Sciences Corporation; Xi Ning; Wang Ruyong; Wang Liang; (112 pag.)CN104016979; (2017); B;,
Bromide – Wikipedia,
bromide – Wiktionary