Author: Jessica.F

Related Products of 583-70-0, 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 583-70-0 as follows.

According to Scheme 1 Step i: To a solution of 1-bromo-2,4-dimethyl-benzene (20.00 g, 108.07 mmol, 1.00 eq) in THF (100 mL) under N2 atmosphere and cooled to -70C, was added n-BuLi (2.5 M, 45.39 mL, 1.05 eq) dropwise. The reaction mixture was stirred at -70C for 2 hr. Then a solution of 1,4-dioxa-spiro[4.5]decan-8-one (17.72 g, 113.47 mmol, 1.05 eq) in THF (100 mL) was added dropwise at -70C, the reaction mixture was stirred at -70C for 2 hr. The reaction mixture was quenched by water (300 mL) and extracted with EtOAc (200 mLx2). The organic layer was dried over Na2SO4 and concentrated in vacuo. The crude product was purified by flash column chromatography on silicagel (Petroleum ether/EtOAc 10/1 to 5/1). Intermediate 2a (24.00 g, 86.00 mmol, 79.57% yield) was obtained as a light yellow solid. 1H NMR (DMSO-d6; 400MHz) delta 7.31-7.29 (m, 1H), 6.90-6.89 (m, 2H), 4.66 (s, 1H), 3.87 (s, 4H), 2.49 (s, 3H), 2.21 (s, 3H), 2.00-1.94 (m, 4H), 1.79-1.76 (m, 2H), 1.53-1.51 (m, 2H).

According to the analysis of related databases, 583-70-0, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Pragma Therapeutics; DUVEY, Guillaume; CELANIRE, Sylvain; (118 pag.)EP3459939; (2019); A1;,
Bromide – Wikipedia,
bromide – Wiktionary

Some common heterocyclic compound, 348-57-2, name is 1-Bromo-2,4-difluorobenzene, molecular formula is C6H3BrF2, 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. HPLC of Formula: C6H3BrF2

To a clean and dry 72 L round bottom flask was added l-bromo-2,4-difluorobenzene (1586 g, (0373) 1.15 equiv, Oakwood lot H4460) and MTBE (20 L, 12.6 vol). This solution was cooled to – 70 to -75 °C and treated with n-BuLi (3286 mL, 1.15 equiv, 2.5 M in hexanes, SAFC lot 32799MJ), added as rapidly as possible while maintaining -75 to -55 °C. This addition typically required 35-45 minutes to complete. (NOTE: If the n-BuLi is added slowly, a white slurry will form and this typically gives poor results). After stirring at -70 to -65 °C for 45 minutes, a solution of compound 3-Br (2000 g, 1.0 equiv, AMRI lot 15CL049A) in MTBE (3 vol) was added rapidly (20-30 min) by addition funnel to the aryl lithium solution while maintaining -75 to -55 °C. After stirring for 30-60 minutes at -75 to -55 °C, the reaction was analyzed by GC/MS and showed only trace (0.5percent AUC) l-bromo-2,4-difluorobenzene present. The reaction was slowly quenched with aqueous 2 M HQ (3.6 L) and allowed to warm to room temperature. The mixture was adjusted to pH = 6.5 to 8.5 using NaHCC>3 (4 L), and the organic layer was separated. The MTBE layer was washed with brine (5percent NaCl in water, 4 L), dried over MgS04, filtered, and concentrated. In order to convert the intermediate hemi-acetal to 4, the crude mixture was heated inside the 20 L rotovap flask at 60-65 °C for 3 hours (under vacuum), at this point all the hemi-acetal was converted to the desired ketone 4- Br by *H NMR (CDC13). This provided crude compound 4-Br [2.36 kg, 75percent (AUC) by HPLC] as a brown oil that solidified upon standing. This material can then be used “as-is” in the next step without further purification.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 348-57-2, its application will become more common.

Reference:
Patent; VIAMET PHARMACEUTICALS, INC.; HOEKSTRA, Willam, J.; YATES, Christopher, M.; WO2015/143142; (2015); A1;,
Bromide – Wikipedia,
bromide – Wiktionary

Adding a certain compound to certain chemical reactions, such as: 399-94-0, name is 1-Bromo-2,5-difluorobenzene, 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 399-94-0, name: 1-Bromo-2,5-difluorobenzene

General procedure: To an oven-dried 25 mL Schlenk tube containing a stirring bar was added 4.5 mg Pd(OAc)2 (0.02 mmol), 15.7mg nBuPAd2 (0.44 mmol), 2-bromofluorobenzene (0.50 mmol), salicylaldehyde (0.50 mmol), potassium carbonate (1.0 mmol). The Schlenk tube was vacuumed and then purged with argon before DMF (2.0 mL) was injected using a syringe. Afterwards the Schlenk tube in the ice bath was degassed by evacuation and back fillingwith argon three times. The reaction mixture was then stirred for 12 h at 120 C. After the reaction was complete,the reaction mixture was diluted with water (5 mL), extracted with ethyl acetate (3 x 10 mL) and dried withanhydrous Na2SO4. After filtration and addition of silica gel into the solution, the organic solvent was reduced evaporated. The crude product was purified by column chromatography using ethyl acetate/n-pentane.

If you are interested in these compounds, you can also browse my other articles.Thank you for taking the time to read this article. I hope you enjoyed it.

Reference:
Article; Shen, Chaoren; Wu, Xiao-Feng; Synlett; vol. 27; 8; (2016); p. 1269 – 1273;,
Bromide – Wikipedia,
bromide – Wiktionary

Electric Literature of 2862-39-7, 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 2862-39-7 as follows.

prepared as follows. Beta Alanine t-butyi ester, 10 nimoi, is dissolved in alcoholic sodium carbonate (O. I M), and 10 mmol of 2-NN ‘ dimethylamino ethyl bromide hydrobromide added thereto with stirring at room temperature, with the pH being monitored and maintained between 8.5 and 9.0 with the addition of aquous sodium hydroxide (1 M) as needed. Following cessation of base uptake, the reaction mixture is yophilized, and the product taken up in propanoi, free of inorganic salts.

According to the analysis of related databases, 2862-39-7, the application of this compound in the production field has become more and more popular.

Reference:
Patent; THROMBOLTYICS, LLC; CHIBBER, Bakshy, A.; (41 pag.)WO2016/73493; (2016); A2;,
Bromide – Wikipedia,
bromide – Wiktionary

Electric Literature of 13633-25-5, 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. 13633-25-5, name is 1-Bromo-4-phenylbutane belongs to bromides-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below.

17C Methyl 1-(4-phenylbutyl)-3-formylindole-5-carboxylate A solution of methyl 3-formylindole-5-carboxylate (2.234 g, 11.0 mmol) and potassium tert-butoxide (1.259 g, 11.2 mmol) in dry N,N-dimethylformamide (50 ml) was added with 1-bromo-4-phenylbutane (2.385 g, 11.2 mmol) and left under stirring at room temperature for 18 h. After that the solvent was evaporated off under reduced pressure, the resulting residue was partitioned between a NaCl saturated solution (50 ml) and chloroform (50 ml) and the aqueous phase was extracted with chloroform (3*50 ml). After drying and evaporating off the solvent under reduced pressure, a crude was obtained which was purified by chromatography through a silica gel column, eluding with n-hexane:ethyl acetate, 70:30, thereby obtaining 2.847 g of the title compound (87% yield). 1 H N.M.R. (300 MHz, CDCl3) delta ppm: 1.66 (m, 2H); 1.91 (m, 2H); 2.64 (t, 2H); 3.93 (s, 3H); 4.16 (t, 2H); 7.11 (d, 2H); 7.19 (m, 1H); 7.25 (d, 2H); 7.33 (d, 1H); 7.70 (s, 1H); 8.01 (dd, 1H); 8.99 (s, 1H); 9.98 (s, 1H).

The synthetic route of 1-Bromo-4-phenylbutane has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Laboratorios Menarini S.A.; US5990142; (1999); A;,
Bromide – Wikipedia,
bromide – Wiktionary

Synthetic Route of 1435-51-4, 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. 1435-51-4 name is 1,3-Dibromo-5-fluorobenzene, 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.

A mixture of Pd(OAc)2 (88 mg, 0.394 mmol) and BINAP (294 mg, 0.473 mmol) in dioxane (8 mL) was stirred in a sealed tube for ~5 min. To the mixture was then added l,3-dibromo-5-fluorobenzene (0.496 mL, 3.94 mmol) and (tetrahydro-2H-pyran- 4-yl)methanamine hydrochloride (299 mg, 1.969 mmol), stirring was continued for additional ~5 min and KOtBu (486 mg, 4.33 mmol) was added. The resulting mixture was heated at 93 C for ~18 hrs. The reaction mixture was cooled to room temperature, diluted with EtOAc (-50 mL) and MeOH (-10 mL), filtered off and concentrated under reduced pressure. The residue was purified by column chromatography [silica gel, 40 g, EtOAc/heptane = 5/95 to 30/70] providing 3-bromo-5-fluoro-N-((tetrahydro-2H-pyran- 4-yl)methyl)aniline (220 mg) as a colorless liquid. LCMS (m z): 289.9 [M+H]+; Rt = 1.03 min.

At the same time, in my other blogs, there are other synthetic methods of this type of compound, 1,3-Dibromo-5-fluorobenzene, and friends who are interested can also refer to it.

Reference:
Patent; NOVARTIS AG; PFISTER, Keith B; SENDZIK, Martin; WO2011/26917; (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. 54962-75-3, name is 3-Bromo-5-(trifluoromethyl)aniline, A new synthetic method of this compound is introduced below., category: bromides-buliding-blocks

1,1-Cyclopropanedicarboxylic acid (2 g, 15.4 mmol) was dissolvedin anhydrous CH2Cl2, anhydrous triethylamine (2.2 mL) wasadded under nitrogen. The mixture was stirred on the ice-bath for30 min. Thionyl chloride (1.2 mL) in anhydrous CH2Cl2 was addeddropwise to the above mixture and stirring for 2 h. 5-bromo-3-(trifluoromethyl)-benzenamine (3.6 g, 15.4 mmol)dissolved inanhydrous CH2Cl2 was added into the mixture. Stirring wascontinued for 2 h and the solution was adjusted to pH 10 withNaOH (2 mol/L), after filtration and concentration in vacuo, anappropriate amount of water was added to the residues.The productwas extracted with ethyl acetate (50 mL), The organic layer wasseparated and the aqueous layer was adjusted to pH 2 with HCl(2 mol/L). The product was extracted with ethyl acetate (50 mL 3)again. The combined organic layer was concentrated in vacuo, totalyielding 1-[[(3,5-dimethylphenyl)amino]carbonyl] (9) (0.8 g, 37%).

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; Zhang, Lin; Shan, Yuanyuan; Li, Chuansheng; Sun, Ying; Su, Ping; Wang, Jinfeng; Li, Lisha; Pan, Xiaoyan; Zhang, Jie; European Journal of Medicinal Chemistry; vol. 127; (2017); p. 275 – 285;,
Bromide – Wikipedia,
bromide – Wiktionary

Related Products of 45762-41-2, 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. 45762-41-2, name is 4-Bromo-2-ethylaniline belongs to bromides-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below.

A solution of 4-bromo-2-ethylaniline (1.09g) in chloroform (20ml) was stirred at room temp. then treated with potassium acetate (0.49g) followed by acetic anhydride (0. 95ml). 18-Crown-6 (0.26g) and t-butylnitrite (1. 32ml) were added after 30 min and the mixture was stirred at reflux for 18h. The reaction mixture was diluted with chloroform and washed with saturated aqueous sodium hydrogen carbonate. The organic phase was separated using a hydrophobic frit and the solvent was evaporated to give the title compound as a brown solid (l. Og). NMR : 8H [CDC13] 8.30 (1H, d), 7.79 (1H, s), 7.63 (1H, d), 2.74 (3H, s), (2.55 (3H, s).

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, 4-Bromo-2-ethylaniline, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; SMITHKLINE BEECHAM CORPORATION; WO2004/10995; (2004); A1;,
Bromide – Wikipedia,
bromide – Wiktionary

Reference of 327-51-5, 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. 327-51-5, name is 1,4-Dibromo-2,5-difluorobenzene, This compound has unique chemical properties. The synthetic route is as follows.

Under argon stream, 1,2-dimethylimidazole (385 mg, 4.0 mmol), 1,4-dibromo-2,5-difluorobenzene (272 mg, 1.0 mmol)Potassium acetate (393 mg, 4.0 mmol) and palladium acetate (11 mg, 0.05 mmol) were suspended in dimethylacetamide (DMAc, 5.0 mL) and stirred at 150 C. for 48 hours. After allowing to cool, water was added to the reaction mixture, the precipitated solid was collected by filtration,Washing with water yielded the desired 1,4-bis(1,2-dimethylimidazol-5-yl)-2,5-difluorobenzene as a milky white solid (198 mg, 66%).

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; Tosoh Corporation; Sagami Chemical Research Institute; Aihara, Hidenori; Yamagata, Takuya; Hachiya, Hitoshi; Watanabe, Makoto; Fukuda, Takashi; Ueda, Saori; Miyashita, Masato; (64 pag.)JP2018/168149; (2018); A;,
Bromide – Wikipedia,
bromide – Wiktionary

Electric Literature of 49764-63-8, A common heterocyclic compound, 49764-63-8, name is 4,5-Dibromobenzene-1,2-diamine, molecular formula is C6H6Br2N2, 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 100 ml of toluene, 10 g (0.036 mol) of the compound of example 12.3, 9.65 g (0.079 mol) of phenylboronic acid, 10 g of potassium carbonate and 1 .05 g of tetrakistriphenylphosphinepalladium was heated at 70C for 5 h. Then, the reaction mixture was mixed with water. The phases were separated to give 10.7 g of a crude product which was purified by column chromatography (toluene) to give 8.1 g (79%)

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; BASF SE; Koeneman, Martin; Materan, Gabriele; Bagain, Plast Gerhard; Ivanovic, Sorin; St., Robert; (100 pag.)KR2016/38052; (2016); A;,
Bromide – Wikipedia,
bromide – Wiktionary