Month: July 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. 656-64-4, name is 3-Bromo-4-fluoroaniline, A new synthetic method of this compound is introduced below., Formula: C6H5BrFN

4-Amino-N-hydroxy-1,2,5-oxadiazol-3-methylimidoyl chloride (36.78 g, 0.23 mol, 1.0 eq)Dissolved in water (318 ml), stirred at 60 C, and added 3-bromo-4-fluoroaniline (47.50 g, 0.25 mol, 1.1 eq).Stir at 60 C for about 10 min,NaHCO3 (29.40 g, 0.35 mmol, 1.5 eq) in water (318 mL) was added dropwiseThe solution was added dropwise after 20 minutes, and the mixture was stirred at 60 C for 30 min, cooled to room temperature, and the reaction solution was suction filtered.The filter cake was washed with water, the filter cake was drained, beaten with water overnight, and filtered by suction the next day to obtain a gray solid, which was dried.The objective product was obtained (61.21 g, yield: 84.2%).

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; Nanjing Yaojie Good Health Biological Technology Co., Ltd.; Wu Yongqian; Li Lin; (48 pag.)CN108727361; (2018); A;,
Bromide – Wikipedia,
bromide – Wiktionary

Adding a certain compound to certain chemical reactions, such as: 52997-43-0, name is 7-(Bromomethyl)pentadecane, 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 52997-43-0, Formula: C16H33Br

The aqueous NaOH solution (13.5 ml, 6 M) was placed in a reaction flask,Ventilation (nitrogen) three times,A solution of p-bromophenethyl mercaptan (9.77 g, 45 mmol) was added dropwise under nitrogen,After dripping,The phase transfer catalyst was added tetrabutylammonium iodide (catalyst amount, 1.99 g).Ten minutes later, 61 ml of tetrahydrofuran was added,To be uniform,Ethyl 2-hexyl decane (16.50 g, 54 mmol) was added dropwise over 10 min.The temperature was then raised to 45 C,The reaction was stirred overnight under vigorous stirring.Reaction is completed,The reaction solution was poured into dilute hydrochloric acid (1 M)Extracted with dichloromethane,Dried over anhydrous sodium sulfate,The solvent was distilled off under reduced pressure,The column was crystallized from 16.3 g of a colorless transparent liquid in 85% yield.

At the same time, in my other blogs, there are other synthetic methods of this type of compound, 7-(Bromomethyl)pentadecane, and friends who are interested can also refer to it.

Reference:
Patent; Beijing Institute of Printing; Wang, Wenguang; Yang, Mingcong; Pu, Jialing; (29 pag.)CN104961665; (2017); B;,
Bromide – Wikipedia,
bromide – Wiktionary

Electric Literature of 74586-53-1,Some common heterocyclic compound, 74586-53-1, name is 3-Bromo-5-methylaniline, molecular formula is C7H8BrN, 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: The amino phenyl derivative (0.4 mmol, 1 equiv) was dissolvedin pyridine absolute (3 mL) and was spiked with sulfonyl chloride/acid chloride (1.5 equiv). The reaction mixture was stirred overnightat rt (refluxed in case of amide coupling). The reaction wasquenched by adding 10 mL of 2 N HCl and extracted with ethylacetate (3 50 mL). The organic layers werewashed with saturatedNaHCO3 (50 mL) and brine (50 mL), dried over magnesium sulfate,filtered and concentrated to dryness. The product was purified byCC. Thetitle compound was prepared by reaction of 3-bromo-5-methylaniline (1000 mg, 5.38 mmol, 1 equiv) andcyclopropanesulfonyl chloride (1013 mg, 8.07 mmol, 1.5 equiv) according to MethodC. The product was purified by CC (hexane/ethyl acetate 8:2); yield: 77% (1200mg). 1H NMR (500 MHz, acetone-d6) delta 8.62 (br. s, 1H), 7.35 (s, 1H), 7.15(s, 1H), 7.13 (s, 1H), 2.65-2.61 (m, 1H), 2.30 (s, 3H), 1.00-0.95 (m, 4H).

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-5-methylaniline, its application will become more common.

Reference:
Article; Abdelsamie, Ahmed S.; Bey, Emmanuel; Gargano, Emanuele M.; Van Koppen, Chris J.; Empting, Martin; Frotscher, Martin; European Journal of Medicinal Chemistry; vol. 103; (2015); p. 56 – 68;,
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. 1073-39-8, name is 3-Bromobicyclo[4.2.0]octa-1,3,5-triene, This compound has unique chemical properties. The synthetic route is as follows., Formula: C8H7Br

To 4-bromobicyclo[4.2.0]octa-1,3,5-triene (1, 3.25 g, 7,76 mmol) in dioxane (30 mL) were added tert-butyl carbamate (2.53 g, 21.6 mmol), cesium carbonate (9.2 g, 28.24 mmol), 4,5-bis(diphenylphosphino)-9,9-dimethylxanthene (O.5g, 0.86 mmol), andtris(dib enzylideneacetone)dipalladium-chloroform adduct (0.3 g, 0.29 mmol). The reaction mixture was stirred at 105 C under nitrogen overnight. The reaction mixture was poured into water, and extracted with ethyl acetate. The organic layer was washed with brine, dried over sodium sulfate, and filtered. The filtrate was concentrated, and purified with silica gel column chromatography eluting with 20% to 100% ethyl acetate in hexane to give product (2).

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 1073-39-8.

Reference:
Patent; PLEXXIKON INC.; ZHANG, Jiazhong; POWERS, Hanna; ALBERS, Aaron; PHAM, Phuongly; WU, Guoxian; BUELL, John; SPEVAK, Wayne; (449 pag.)WO2018/57973; (2018); A1;,
Bromide – Wikipedia,
bromide – Wiktionary

Synthetic Route of 2695-48-9, 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 2695-48-9 as follows.

To a stirred suspension of sodium hydride (840mg of a 60% dispersion in oil, 21.0mmol) in N,N- dimethylformamide (40ml) was added in one portion di-fe/t-butyl iminodicarbamate (4.56g, 21.0mmol). After stirring for 40mins, 8-bromooct-1-ene (3.50ml, 21mmol) was added and mixture was stirred at room temperature overnight. The solvent was removed in vacuo and the residue dissolved in water and ethyl acetate. The organic layer was separated and washed with water then brine, dried (magnesium sulphate) and the solvent removed in vacuo. The residue was purified by column chromatography on silica gel eluting with diethyl ethe?pentane (1/99 to 6/94 by volume) to furnish the title compound as a clear oil, 5.51 g.

According to the analysis of related databases, 2695-48-9, the application of this compound in the production field has become more and more popular.

Reference:
Patent; PFIZER LIMITED; WO2007/107828; (2007); A2;,
Bromide – Wikipedia,
bromide – Wiktionary

Related Products of 2789-89-1, 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. 2789-89-1, name is 1,2-Bis(4-bromophenyl)ethyne belongs to bromides-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below.

A small molecule luminescent material (P37) based on 1,2-diphenylacetylene as the acceptor unit,The specific steps are:Under nitrogen protection,To a three-necked flask was added 100 ml of toluene,1 g of intermediate 1 (2.99 mmol),2.14 g of 9-phenyl-3-carbazole boronic acid (7.45 mmol, 2.5 equ)Under stirring, 3.47 g of sodium tert-butyl alcohol was added,Then add 230 mg of palladium acetate,0.5 mL of tri-tert-butylphosphine,90 & lt; 0 & gt; C overnight.Cooling, extraction of organic phase with methylene chloride, spin dry,Column. To give 1.48 g of product as a yellow solid in 75% yield.

The synthetic route of 1,2-Bis(4-bromophenyl)ethyne has been constantly updated, and we look forward to future research findings.

Reference:
Patent; South China University of Technology; Su Shijian; He Zuozheng; Ma Wuguang; Peng Junbiao; Cao Yong; (30 pag.)CN106242976; (2016); A;,
Bromide – Wikipedia,
bromide – Wiktionary

Reference of 69321-60-4,Some common heterocyclic compound, 69321-60-4, name is 2,6-Dibromotoluene, molecular formula is C7H6Br2, 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 250-mL single-neck round-bottomed flask equipped with a magnetic stirrer, reflux condenser and nitrogen inlet was purged with nitrogen and charged with 2,6-dibromotoluene (2.50 g, 10.0 mmol), N-bromosuccinimide (1.78 g, 10.0 mmol) and carbon tetrachloride (40 iriL). The solution was heated to 80 C (oil bath temperature), and 2,2′-azobisisobutyronitrile (164 mg, 1.00 mmol) was added. The resulting mixture was refluxed for 14 h. After that time, the mixture was cooled to room temperature and filtered. The filter cake was washed with carbon tetrachloride (2 x 20 iriL). The filtrate was diluted with ethyl acetate (200 iriL) and washed with water (40 mL), saturated aqueous sodium bicarbonate (40 iriL) and brine (40 iriL). The organic layer was dried over sodium sulfate and concentrated under reduced pressure to afford a quantative yield (3.28 g) of l,3-dibromo-2-(bromomethyl)benzene as a yellow solid: mp 77-78 C; ]H NMR (300 MHz, CDC13) delta 7.55 (d, 2H, / = 8.1 Hz), 7.07 (t, IH, 7 = 8.1 Hz), 4.83 (s, 2H)

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

Reference:
Patent; GILEAD CONNECTICUT, INC.; GENENTECH, INC.; BARBOSA, Antonio, J., M.; BLOMGREN, Peter, A.; CURRIE, Kevin, S.; KRISHNAMOORTHY, Ravi; KROPF, Jeffrey, E.; LEE, Seung H.; MITCHELL, Scott A.; ORTWINE, Daniel; SCHMITT, Aaron, C.; WANG, Xiaojing; XU, Jianjun; YOUNG, Wendy; ZHANG, Honglu; ZHAO, Zhongdong; ZHICHKIN, Pavel E.; WO2011/140488; (2011); A1;,
Bromide – Wikipedia,
bromide – Wiktionary

Synthetic Route of 10485-09-3, A common heterocyclic compound, 10485-09-3, name is 2-Bromoindene, molecular formula is C9H7Br, 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 1.45 g (63.5 mmol) piece of magnesium was charged into a sufficiently dried and argon-substituted 200 mL reactor, and stirred vigorously 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 2.93 g (15.0 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 dryer, remaining after dropping of the reaction drop) It stirred at room temperature after completion | finish for 2 hours.The reaction solution is diluted with 9.00 mL (75.3 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 20 hours while returning to room temperature. After distilling off the solvent of the reaction solution and unreacted dimethylsilyl dichloride, 10 mL of tetrahydrofuran and 1.50 mL (16.0 mmol) of 1,3-dimethyl-2-imidazolidinone were added to the residue.Synthesized by the method described in JP-A-201-145240 in a fully dried, argon-substituted 100 mL reactor.5.03 g (15.0 mmol) of 7- (3,5-di-tert-butyl-4-methoxyphenyl) -1-indene and 15 mL of tetrahydrofuran are charged, and 9.70 mL of n-butyllithium solution (hexane solution, 55 M (15.0 mmol) was added and 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 19 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 desired product represented by the following formula (A-2L) (hereinafter referred to as compound (A-2L)) Was obtained as an isomer mixture of 5.08 g (yield 67%).

The synthetic route of 10485-09-3 has been constantly updated, and we look forward to future research findings.

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

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. 2862-39-7, name is 2-Bromo-N,N-dimethylethanamine hydrobromide, A new synthetic method of this compound is introduced below., HPLC of Formula: C4H11Br2N

General procedure: To the suspension of compound 11a-11e or 13 (1.5 mmol) inDCM (3 mL) was added TFA (3 mL). The mixturewas stirred at roomtemperature for 2 h and was concentrated under vacuum. Theproduct was then dissolved in DMF (6 mL) and added Et3N (1 mL)without further purification. The reaction mixture was stirred for1 h and was added CS2 (0.14 mL, 2.25 mmol) to continuously stir for 30 min. A series of different of halogen or alkene substitutedcompounds (1.5 mmol) were added respectively and the mixturewas stirred at 50 C overnight. The mixture was cooled to roomtemperature and extracted with dichloromethane (20 mL x 3). Theorganic phase was washed with brine (15mL x 3), dried overanhydrous Na2SO4 and concentrated under vacuum. The residuewas purified by column chromatography to provide the target products.

The synthetic route of 2862-39-7 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Su, Yue; Li, Ridong; Ning, Xianling; Lin, Zhiqiang; Zhao, Xuyang; Zhou, Juntuo; Liu, Jia; Jin, Yan; Yin, Yuxin; European Journal of Medicinal Chemistry; vol. 177; (2019); p. 32 – 46;,
Bromide – Wikipedia,
bromide – Wiktionary

Synthetic Route of 74586-53-1, These common heterocyclic compound, 74586-53-1, name is 3-Bromo-5-methylaniline, 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 mixture of 3-bromo-5-methyl-aniline (1.86 g, 10 mmol), 2-chloroethanol (3.22 g, 40.00 mmol), KI (166 mg, 1.00 mmol) and CaCO3 (2.00 g, 20.00 mmol) in water (6 mL) and EtOH (6 mL) was heated at 100C for 36h, then at 120C for 20h. The reaction mixture was cooled to RT, diluted with EtOAc, washed with H20, sat. NaC1 and dried then evaporated under reduced pressure. The crude material was subjected to ISCO purification (40g silica; 0 % to 10% of MeOH in DCM) to give 2- [3-bromo-N-(2-hydroxyethyl)-5-methyl-anilino] ethanol YL4a (1.4 g, 51%). ?HNMR (300 MHz, CDC13) oe 6.71 (d, J = 22.0 Hz, 2H), 6.47 (s, 1H), 3.87 (t, J = 4.9 Hz, 4H), 3.61 – 3.53 (m, 4H), 3.41 (s, 2H), 2.29 (s, 3H) ppm. ESI-MS m/z calc. 273.04, found 274.31 (M+1)+; Retention time: 0.68 minutes.

The synthetic route of 74586-53-1 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; VERTEX PHARMACEUTICALS INCORPORATED; DAVIES, Robert, J.; CAO, Jingrong; COCKERILL, Meghan, Elise; COLLIER, Philip, Noel; DENINNO, Michael, Paul; DOYLE, Elisabeth; FRANTZ, James, Daniel; GAO, Huai; GOLDMAN, Brian, Anthony; GREY, Ronald, Lee; GRILLOT, Anne-laure; GU, Wenxin; HENDERSON, James, A.; IRARRAZAVAL, Raul Eduardo, Krauss; KOLPAK, Adrianne, Lynn; LIAO, Yusheng; MAGAVI, Sanjay Shivayogi; MALTAIS, Francois; MESSERSMITH, David; PIERCE, Albert, Charles; PEROLA, Emanuele; RYU, Elizabeth Jin-Sun; SYKEN, Joshua; WANG, Jian; (706 pag.)WO2016/197009; (2016); A1;,
Bromide – Wikipedia,
bromide – Wiktionary