Month: July 2021

Application of 45762-41-2,Some common heterocyclic compound, 45762-41-2, name is 4-Bromo-2-ethylaniline, molecular formula is C8H10BrN, 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.

EXAMPLE 1: SYNTHESIS OF COMPOUNDS COMPOUND 1 : 2-(1,8-DIETHYL-6-PHENYL-1,3,4,9-TETRAHYDRO-PYRANO[3,4-B]INDOL-1- YL)-ETHANOL I. A. SYNTHESIS OF N-(4-BROMO-2-ETHYL-PHEHYL)-2-HYDROXIMINO-ACETOAMIDE To a suspension of 4-bromo-2-ethylaniline (50.0 g, 250 mmol) in water (1000 mL) was added concentrated hydrochloric acid (25 mL), sodium sulfate (220 g), and hydroxylamine hydrochloride (56.25 g), followed by addition of chloral hydrate (44.0 g). The reaction mixture was heated to 90C using an oil bath for 1 hour. After cooling down to room temperature, it was extracted with ethyl acetate. Extract was dried over magnesium sulfate and concentrated under reduced pressure to give the title compound (31.1 g, 46% YIELD). 1H NMR (DMSO-d6) 5 12.24 (s, 1H), 9.56 (s, 1H), 7. 68 (s, 1H), 7.41 (m, 3H), 2. 58 (q, 2H), 1.11 (t, 3H). 47. A. Synthesis of N-(4-Bromo-2-ethyl-phenyl)-2-hydroxyimino-acetamide Following the procedure of example 36. A. except using 4-bromo-2-ethylaniline as the aniline component afforded the title compound as a solid. ESI (-) MS m/e=269 (MH-).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 4-Bromo-2-ethylaniline, its application will become more common.

Reference:
Patent; SALMEDIX, INC.; WO2005/33112; (2005); A2;,
Bromide – Wikipedia,
bromide – Wiktionary

Related Products of 39478-78-9, 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. 39478-78-9, name is 5-Bromo-2-methylaniline, This compound has unique chemical properties. The synthetic route is as follows.

Step A: 5-Bromo-8-methyl-quinoline A solution of 5-Bromo-2-methylaniline (7.44 g), glycerol (7.4 g), nitrobenzene (4.9 g) in 75% sulfuric acid (20 ml) was heated at 150 C. for 3 hrs. The solution was cooled to 0 C. then carefully neutralized with aqueous sodium hydroxide. The reaction mixture became a dark gum and was diluted with water and extracted three times with ethyl acetate. The combined organic layers were washed with saturated brine, then dried with sodium sulphate and the solvent removed in vacuo. The crude product was purified by column chromatography (dichloromethane) to afford the title compound as a solid (6 g). 1H-NMR (CDCl3, 400 MHz) 8.91 (m, 1H), 8.51 (m, 1H), 7.7 (m, 1H), 7.50 (m, 1H), 7.4 (m, 1H), 2.72 (s, 3H).

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

Reference:
Patent; SYNGENTA CROP PROTECTION LLC; US2012/238517; (2012); A1;,
Bromide – Wikipedia,
bromide – Wiktionary

Adding a certain compound to certain chemical reactions, such as: 627871-16-3, name is 5-Bromo-4-fluoro-2-methylaniline, 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 627871-16-3, Application In Synthesis of 5-Bromo-4-fluoro-2-methylaniline

At room temperature,The raw aniline compound (10 g, 49.0 mmol) was dissolved in 20 mL of pyridine, and the raw material was added4-nitro-2-carboxylate methylbenzenesulfonyl chloride (16.45 g, 58.8 mmol),Reaction at room temperature for more than 8 hours.After the reaction was monitored by TLC, the reaction was cooled to room temperature.Add 1N hydrochloric acid, adjust the pH to 3 ~ 4, precipitate a pale yellow precipitate, filter,Drying gave Intert I (18.6 g, yield: 84.9%). Can be used directly in the next reaction.

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

Reference:
Patent; Shanghai Jiao Tong University School of Medicine; Zhang Jian; Zhao Mingzhu; Wei Jiacheng; (23 pag.)CN110642757; (2020); A;,
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. 2635-13-4, name is 5-Bromobenzo[d][1,3]dioxole, A new synthetic method of this compound is introduced below., Product Details of 2635-13-4

General procedure: A 25 mL Schlenk tube was charged with Cu2O (0.05 mmol), ArX (0.5 mmol), NHR1R2 (0.75 mmol), NaOH (1 mmol), TBAB (0.1 mmol), L2 (0.1 mmol) and H2O/EtOH (1 mL, 1/1, v/v). The mixture was stirred at 120 C for 12 h. The reaction mixture was extracted with ethyl acetate (3 10 mL), washed with water and brine, dried over anhydrous Na2SO4, and concentrated in vacuo. The residue was purified by flash column chromatograph on silica gel(ethyl acetate/petroleum ether as the eluent) to provide the target products 3a-3w and 6.

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:
Article; Xie, Jian-Wei; Yao, Zhen-Bin; Wang, Xiao-Chuang; Zhang, Jie; Tetrahedron; vol. 75; 27; (2019); p. 3788 – 3792;,
Bromide – Wikipedia,
bromide – Wiktionary

These common heterocyclic compound, 67344-77-8, name is 1-(3-Bromophenyl)-N-methylmethanamine, 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. SDS of cas: 67344-77-8

To a solution of 1-(3-bromophenyl)-N-methylmethanamine (12.0 g) and N-(tert-butoxycarbonyl)glycine (11.5 g) in dichloroethane (80 ml) were added HOBt (9.7 g) and WSC hydrochloride (13.7 g), followed by stirring at room temperature overnight. To the reaction mixture was added a saturated aqueous sodium hydrogen carbonate solution, followed by extraction with CHCl3. The mixture was dried over Na2SO4 and then concentrated under reduced pressure. The obtained residue was purified by silica gel column chromatography (CHCl3/MeOH) to obtain tert-butyl {2-[(3-bromobenzyl)amino]-2-oxoethyl}carbamate (21.3 g).

The synthetic route of 1-(3-Bromophenyl)-N-methylmethanamine has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Astellas Pharma Inc.; US2012/184520; (2012); 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., Recommanded Product: 1-Bromo-2-cyclohexylethane

Step 1: Preparation of ethyl 9-(2-c> elohexyIeth()xy)-6-ethyI-10-methoxy-2-oxo-6,7- dihydrobenzo [a] qiiinolizine-3-earbox late A mixture of ethyl 6-ethyl-9-hydroxy-10-methoxy-2-oxo-6,7-dihydroberizo[a]quinolizme- 3-carboxylate (50 mg, 0.15 mmol), 2 – b ro mo e t h y 1 c y c 1 o h e x a n e (57 mg, 0.3 mmol) and K2CO3 (62 mg, 0.45 mmol) in DMF (2 ml.) was stirred at 80 C for 2 hours. Water was added and the mixture was extracted with ethyl acetate. The organic phase was dried over anhydrous Na^SOj and then concentrated in vacuo to give crude ethyl 9-(2-cyclohexylethoxy)-6-ethyl- 10-methoxy- 2-0X0-6, 7-dihydrobenzo[a]qiiinolizine-3-carboxylate (69 mg) which was used in the next step without 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; F. HOFFMANN-LA ROCHE AG; HOFFMANN-LA ROCHE INC.; HAN, Xingchun; JAVANBAKHT, Hassan; JIANG, Min; LIANG, Chungen; WANG, Jianping; WANG, Yongguang; WANG, Zhanguo; WEIKERT, Robert James; YANG, Song; ZHOU, Chengang; WO2015/113990; (2015); A1;,
Bromide – Wikipedia,
bromide – Wiktionary

4549-33-1, name is 1,9-Dibromononane, belongs to bromides-buliding-blocks compound, is considered to be a conventional heterocyclic compound, which is widely used in drug synthesis. The chemical synthesis route is as follows. Application In Synthesis of 1,9-Dibromononane

EXAMPLE 4 N, N’-Nonane-1, 9-diyl-bis-pyridinium Dibromide (bPNB).; 1,9-Dibromononane (mmol) was added to a solution (30 mL) of dry pyridine, and the solution heated for 24 hours at 65C. The resulting precipitate was filtered, and the product washed five times with dry diethyl ether. The resulting clear liquid was isolated in a 87% yield. ‘H NMR (300 MHz, DMSO-D6) 5 9.17 (2H, d, C2&C6-H), 8.61 (1H, t, C4-H), 8. 18 (2H, t, C3&C5-H), 4.63 (2H, t, C’1-CH2), 1.89 (2H, m, C’2-CH2), 1.22 (5H, m, C’3-5-CH2) ; 13C NMR (75 MHz, DMSO-D6) 8 145.3, 144.5, 127.9, 60.5, 30.7, 28.4, 28.2, 25.3.

The synthetic route of 4549-33-1 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; UNIVERSITY OF KENTUCKY RESEARCH FOUNDATION; WO2005/66129; (2005); A2;,
Bromide – Wikipedia,
bromide – Wiktionary

Electric Literature of 18599-22-9, 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 18599-22-9 as follows.

To a stirred solution of silver acetate (10 mg, 0.060 mmol) in glacial acetic acid (20 mL) at reflux temperature was added zinc powder (10 g, 153 mmol) in one portion, and the whole was stirred at that temperature for additional 30 seconds. After refluxing for 30 seconds, the flask was cooled by dipping in an ice-bath. The Zn-Ag couple formed was separated by vacuum filtration in the open-air, which was washed with Et2O several times, followed by drying under reduced pressure. The Zn-Ag couple separated was stored at room temperature under Ar atmosphere. See Figure S1 Preparation of CH2=CHCF2CF2ZnBr in DMF (2-Zn) In a two-necked round-bottomed flask, equipped with a teflon-coated stirrer bar, was placed Zn-Ag couple (0.66 g, 10 mmol) in DMF (5.0 mL). To the suspension was slowly dropwise added 4-bromo-3,3,4,4-tetrafluorobut-1-ene (1, 1.0 g, 5.0 mmol) at 0 C and the whole was stirred at that temperature for 30 min. The resultant was subjected to a short pad of celite and washed by Et2O three times. The filtrate was concentrated in vacuo to give the corresponding organozinc reagents 2-Zn in 86% NMR yield as a 0.70 M DMF solution (1,1,2,2-Tetrafluorobut-3-en-1-yl)zinc bromide in DMF (2-Zn) Yield: 86% (determined by 19F NMR); 19F NMR (CDCl3): 112.10 (brs, 2F, CF2CH), 120.23 (brs, 2F, CF2Zn).

According to the analysis of related databases, 18599-22-9, the application of this compound in the production field has become more and more popular.

Reference:
Article; Tamamoto, Ken; Yamada, Shigeyuki; Konno, Tsutomu; Beilstein Journal of Organic Chemistry; vol. 14; (2018); p. 2375 – 2383;,
Bromide – Wikipedia,
bromide – Wiktionary

Synthetic Route of 698-19-1, 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. 698-19-1 name is 1-(2-Bromophenyl)-N-methylmethanamine, 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.

Preparation of ferf-butyl 2-bromobenzyl(methyl)carbamate (59). 58 59 A solution of compound 58 (2.0 g, 10.0 mmol) and Boc20 (2.29 g, 10.5 mmol) in THF (40 mL) was stirred at RT for 16 hours. The mixture was then concentrated in vacuo. The crude product was purified by flash column chromatography over silica gel, which was eluted with 10% EtOAc in heptanes, and yielded compound 59 as a colorless oil (2.8 g, 95% yield). 1H NMR (400 MHz, CDCI3) delta 7.54 (d, 1 H), 7.30 (t, 1 H), 7.13 (m, 2 H), 4.53 (br d, 2 H), 2.87 (br s, 3 H), 1.46 (br d, 9 H).

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

Reference:
Patent; PFIZER INC.; BAILEY, Simon; BURKE, Benjamin, Joseph; COLLINS, Michael, Raymond; CUI, Jingrong, Jean; DEAL, Judith, Gail; HOFFMAN, Robert, Louis; HUANG, Qinhua; JOHNSON, Ted, William; KANIA, Robert, Steven; KATH, John, Charles; LE, Phuong, Thi, Quy; MCTIGUE, Michele, Ann; PALMER, Cynthia, Louise; RICHARDSON, Paul, Francis; SACH, Neal, William; WO2013/132376; (2013); A1;,
Bromide – Wikipedia,
bromide – Wiktionary

955959-84-9, name is 4-(4-Bromophenyl)dibenzo[b,d]furan, belongs to bromides-buliding-blocks compound, is considered to be a conventional heterocyclic compound, which is widely used in drug synthesis. The chemical synthesis route is as follows. Quality Control of 4-(4-Bromophenyl)dibenzo[b,d]furan

[Example-of-Synthesis 1 (Synthesis of Compound H1) ]; Under an argon gas flow, 6.5 g of Intermediate 5, 9.5 g of Intermediate 12, 2.6 g of t-butoxy sodium (manufactured by Hiroshima Wako Co., Ltd.), 92 mg of tris (dibenzylideneacetone) dipalladium(0) (manufactured by SIGMA-ALDRICH Corn.), 42 mg of tri-tert-butylphosphine and 100 ml of dehydrated toluene were placed and the reaction was allowed to proceed at 80°C for 8 hours. The resultant solution was cooled down, added with 500 ml of water and filtered through sellite. The resultant filtrate was extracted with toluene, and the extract was dried over dehydrated magnesium sulfate. The dried substance was condensed under reduced pressure and the coarse product was subjected to column purification. The purified substance was re-crystallized with a use of toluene and after the resultant crystal was taken by filtration, the crystal was dried and as a result, 8.1 g of a pale yellow powder was obtained. The pale yellow powder was identified as Compound H1 from the result in accordance with the FD-MS analysis.

The synthetic route of 955959-84-9 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Idemitsu Kosan Co., Ltd.; EP2295421; (2011); A1;,
Bromide – Wikipedia,
bromide – Wiktionary