Month: February 2021

Synthetic Route of 1003-99-2, 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. 1003-99-2, name is 2-Bromo-5-fluoroaniline, This compound has unique chemical properties. The synthetic route is as follows.

EXAMPLE 1; Synthesis of l-ethyl-3-[4-fluoro-7-(3-fluoropyridin-2-yl)-5-(pyridin-3-yl)-l,3- benzothiazol-2-yl]urea (Compound No. 1); Step 1 : Synthesis of N-(2-bromo-5-fluorophenyl)-2,2-dimethylpropanamide :; To a solution of 2-bromo-5-fluoroaniline (15.0 g, 85.7 mmol) in dichloromethane (120 mL) were added triethylamine (11.25 g, 110.0 mmol) followed by pivaloyl chloride (11.3 g, 92.0 mmol) drop-wise at 0 0C and then stirred at 25-30 0C for about 4 hours. The reaction mixture was diluted with dichloromethane and washed with saturated solution of sodium bicarbonate followed by water. The organic layer was dried over anhydrous sodium sulfate, filtered and then concentrated to give the crude residue, which was purified through column chromatography using silica gel 230-400 mesh size and eluted with 5percent ethyl acetate in hexane to yield the title compound (20 g)

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

Reference:
Patent; RANBAXY LABORATORIES LIMITED; WO2009/156966; (2009); A1;,
Bromide – Wikipedia,
bromide – Wiktionary

Synthetic Route of 445-02-3, A common heterocyclic compound, 445-02-3, name is 4-Bromo-2-(trifluoromethyl)aniline, molecular formula is C7H5BrF3N, 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.

To 4-thiazolecarboxylic acid (300 mg) and HATU (1.06 g) in dry DCM (10 ml.) was added DIPEA (1.2 ml.) and the reaction mixture was stirred at room temperature under nitrogen for 30 mins. 4-Bromo-2-(trifluoromethyl)aniline (0.33 ml.) was added and the reaction mixture was heated at reflux for 20 h. The reaction mixture was evaporated in vacuo and then purified using a 12 g silica Silicycle cartridge eluting with a gradient of 0 – 100% EtOAc in cyclohexane to give the title compound. MS calcd for (C11H6Br F3N2OS + H)+ : 351/353 MS found (electrospray) : (M+H)+ = 351/353

The synthetic route of 445-02-3 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; SMITHKLINE BEECHAM CORPORATION; WO2008/59042; (2008); A1;,
Bromide – Wikipedia,
bromide – Wiktionary

Some common heterocyclic compound, 33070-32-5, name is 5-Bromo-2,2-difluorobenzodioxole, molecular formula is C7H3BrF2O2, 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. Formula: C7H3BrF2O2

To a mixture of 5-bromo-2,2-difluorobenzo[d][1,3]dioxole (10 g, 42.2 mmol), 2-di-tert-butylphosphino-3,4,5,6-tetramethyl-2′,4′,6′-triisopropyl-1,1′-biphenyl (2.028 g, 4.22 mmol) and potassium hydroxide (4.74 g, 84 mmol) was added degassed water (10 mL). The reaction mixture was sparged with a nitrogen stream for 5 minutes. To the reaction mixture was added a degassed solution of tris(dibenzylideneacetone)dipalladium(0) (0.773 g, 0.844 mmol) in dioxane (10 mL). The combined reaction mixture was sparged with nitrogen for 5-7 minutes. The reaction vial was capped and was stirred at 100 C. overnight (16 hours). The reaction mixture was cooled to ambient temperature, and partitioned between ethyl acetate and aqueous 1 N HCl solution. The organic fractions were combined and washed with brine, dried over anhydrous sodium sulfate, filtered, and concentrated in vacuo, maintaining a bath temperature at or below 25 C. The residue was purified by flash chromatography using a 220 g silica gel cartridge, eluting with 25-75% dichloromethane/heptanes to provide the title compound. 1H NMR (400 MHz, CDCl3) delta ppm 5.51 (s, 1H), 6.50 (dd, J=8.6, 2.5 Hz, 1H), 6.63 (d, J=2.4 Hz, 1H), 6.90 (dd, J=8.7, 1.4 Hz, 1H). MS (ESI-) m/z 173.1 (M-H)-.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 33070-32-5, its application will become more common.

Reference:
Patent; AbbVie S.a.r.l.; Galapagos NV; Altenbach, Robert J.; Bogdan, Andrew; Desroy, Nicolas; Gfesser, Gregory A.; Greszler, Stephen N.; Kym, Philip R.; Liu, Bo; Malagu, Karine Fabienne; Merayo Merayo, Nuria; Pizzonero, Mathieu Rafael; Searle, Xenia B.; Van der Plas, Steven Emiel; Wang, Xueqing; Yeung, Ming C.; Zhao, Gang; (101 pag.)US2018/244640; (2018); A1;,
Bromide – Wikipedia,
bromide – Wiktionary

Electric Literature of 3814-30-0, 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. 3814-30-0, name is (Bromomethyl)cyclopentane, This compound has unique chemical properties. The synthetic route is as follows.

General procedure: 2-(4-(ethylsulfonyl)phenyl)-N-(4-((propylamino)methyl)phenyl)acetamide (50 mg, 0.13 mmol) was added sequentially to a 20 mL sealed tube.2-chlorobenzyl bromide (53 muL, 0.4 mmol),Anhydrous potassium carbonate (55 mg, 0.4 mmol),N,N-dimethylformamide 2mL,Heated at 60 C for 3 hours,TLC confirmed that the reaction was completed and washed with saturated brine.Purification of petroleum ether by column chromatography: ethyl acetate 2:1?3:2,Made a white solid 18mg,The yield was 27.8%.

The chemical industry reduces the impact on the environment during synthesis (Bromomethyl)cyclopentane. I believe this compound will play a more active role in future production and life.

Reference:
Patent; Fudan University; Wang Yonghui; Qiu Ruomeng; Gong Juwen; Tian Jinlong; Huang Yafei; (65 pag.)CN109206346; (2019); A;,
Bromide – Wikipedia,
bromide – Wiktionary

Electric Literature of 24468-88-0, 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. 24468-88-0, name is N-Benzyl-2-bromo-N-(2-bromoethyl)ethanamine belongs to bromides-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below.

To a solution of compound 1-2 (2.56 g, 14.34 mmol) and compound 32-1 (6.905 g, 21.51 mmol) in DMF (15mL) under N2 was added NaH (1.434g, 35.85 mmol, 60% dispersed in Mineral oil). The mixture was stirred at 50 C for18 hours, cooled to rt, and quenched with water (20 mL). The mixture was extracted with EtOAc (150 mL x 3). Thecombined organic phases were washed with water, dried over anhydrous Na2SO4 and concentrated in vacuo. Theresidue was purified by silica gel column chromatography (hexane/EtOAc (v/v) = 8/1) to give the title compound 32-2(0.752 g, 14.9%). The compound was characterized by the following spectroscopic data:MS-ESI: m/z 352.1 [M+H]+; and1H NMR (400 MHz, CDCl3): delta 7.63-7.56 (m, 1H), 7.41-7.22 (m, 6H), 3.82 (d, 6H), 3.56 (s, 2H), 3.03 (s, 2H), 2.98-2.89(m, 2H), 2.24-2.00 (m, 4H), 1.37 (d, J = 11.8 Hz, 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, N-Benzyl-2-bromo-N-(2-bromoethyl)ethanamine, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; Sunshine Lake Pharma Co., Ltd.; ZHANG, Jiancun; ZHANG, Yingjun; XIE, Hongming; REN, Qingyun; LUO, Huichao; YU, Tianzhu; TAN, Yumei; EP2730572; (2015); B1;,
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. 3972-65-4, name is 1-Bromo-4-(tert-butyl)benzene, A new synthetic method of this compound is introduced below., Computed Properties of C10H13Br

Into a 50 mL seal tube was placed 1-bromo-4-tert-butylbenzene (5.0 g, 23.5 mmol), Pd(PPh3)2Cl2 (660 mg, 0.94 mmol), CuI (47 mg, 0.23 mmol), 10 mL of TEA and 20 mL of toluene. This yellow suspension was degassed by bubbling with nitrogen for 10 min, and then 5.0 mL of (trimethylsilyl)acetylene (3.46 g, 35.2 mmol) was added with a syringe. The seal tube is then immediately sealed under nitrogen atm. and heated to 80C and stirred for 12 h. The reaction mixture was allowed to cool to room temperature and was then filtered through celite. The solids were washed thoroughly with ethyl ether until the washings were colourless and the filtrate was evaporated to dryness under reduced pressure. The residue was purified by column chromatography using hexane as the eluent to give 4 as a pale yellow oil. The 1H-NMR spectrum matched with that of the previously reported compound. 5 Isolated yield (4.0 g, 74%)1H NMR (CDCl3, 300 MHz) : 0.31 (s, 9H), 1.37 (s, 9H), 7.33 (d, 2H, J = 8.7 Hz), 7.41 (d, 2H, J = 8.5 Hz).MS-EI : m/z 230.0 [M]+ .

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; Ananth Reddy; Thomas, Anup; Mallesham; Sridhar; Jayathirtha Rao; Bhanuprakash; Tetrahedron Letters; vol. 52; 51; (2011); p. 6942 – 6947;,
Bromide – Wikipedia,
bromide – Wiktionary

Reference of 4117-09-3, A common heterocyclic compound, 4117-09-3, name is 7-Bromo-1-heptene, molecular formula is C7H13Br, 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.

General procedure: Coupling of Alkyl Halides with t-BuMgCl; Procedure 1 (P1)An alkyl halide (1.0 mmol), decane (63 mg as an internal standard)and LiI (5.3 mg, 0.04 mmol) were added to a dry, nitrogen-flushedtest tube equipped with a rubber septum and a magnetic stir bar.THF (0.8 mL) was added and the solution was cooled to -78 C usinga dry ice/EtOH bath. t-BuMgCl (2a) (1.5 mL, 0.81 M in THF,1.2 mmol) was added slowly followed by isoprene (136.2 mg, 2.0mmol). To this mixture was added CoCl2 [2.6 mg, 0.02 mmol, as apowder or as a THF solution (0.5 mL, 0.04 M)]. (Note 1: CoCl2should be added after isoprene, otherwise the catalytic performancedecreases significantly). The cold bath was removed and the mixturewas warmed to r.t. (ca. over 10 min), and then heated for 5 h bysuspending the reaction vessel in an oil bath kept at 50 C. (Note 2:when the reaction mixture was heated at 30 C during this stage, unidentifiedside reactions occurred resulting in low yields of couplingproducts). The resulting mixture was cooled to 0 C in an ice bathand the reaction was quenched with aq HCl (5 mL, 1 M). The productwas extracted with Et2O (3 ¡Á 20 mL). The combined organiclayer dried over Na2SO4, concentrated and analyzed by gas chromatographyto determine the GC yield. The residue was purified by silicagel column chromatography or by GPC. According to P1, 7-bromohept-1-ene (4b) (177 mg, 1.0 mmol) andt-BuMgCl (2a) (0.81 M in THF, 1.2 mmol) were reacted under standardconditions.Yield: 86% (determined by GC using decane as an internal standard).

The synthetic route of 4117-09-3 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Iwasaki, Takanori; Takagawa, Hiroaki; Okamoto, Kanako; Singh, Surya Prakash; Kuniyasu, Hitoshi; Kambe, Nobuaki; Synthesis; vol. 46; 12; (2014); p. 1583 – 1592;,
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. 2550-36-9, name is (Bromomethyl)cyclohexane, This compound has unique chemical properties. The synthetic route is as follows., Formula: C7H13Br

2,6-dihydroxy acetophenone solution (2,6-dihydroxyacetophenone, compound 7, 1.0 eq.), Anhydrous potassium carbonate (anhydrouspotassium carbonate, 2.0 eq.), Dissolved in acetone, alkyl bromide mixture (alkyl bromides, 1.0 eq.) Were mixed and it reacted for 18 hours at 70 ~ 80 . After evaporation of acetone, the remaining reaction product was diluted with dichloromethane and washed three times in water. The organic layer was then collected and concentrated under reduced pressure and then dehydrated with anhydrous Na2SO4 and the crude product obtained by separating the crude product was purified by column chromatography to obtain a compound 9a ~ 9d.

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 2550-36-9.

Reference:
Patent; Chungnam National University Industry-Academic Cooperation Foundation; Chungbuk National University Industry-Academic Cooperation Foundation; Jung, Sang Hun; Kim, Young Soo; (39 pag.)KR101535119; (2015); B1;,
Bromide – Wikipedia,
bromide – Wiktionary

Reference of 4549-33-1, 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. 4549-33-1, name is 1,9-Dibromononane belongs to bromides-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below.

Intermediate 163.trans-4-[(9-bromononyl)(methyl)amino]cyclohexyl 9-methyl-9H-xanthene-9- carboxylate.318 mg (0.90 mmol) of intermediate 162 are dissolved in 12 ml THF. 0.728 ml (3.61 mmol) of 1 ,9-dibromononane and 0.19 ml (1.36 mmol) of triethylamine are added and the system is stirred at 50C for 24 hr. 0.19 additioinal ml of triethylamine are added and the stirring at 50C prosecuted overnight. After a new addition of 1 ,9- dibromononane (0.911 ml; 4.5 mmol) and 72 hr of stirring at 70C the solvents are eliminated, ethyl ether is added and the solids (triethylammonium hydrobromide) filtered. The filtrate is concentrated and purified via SP1 chromatography to give 220 mg (42% yield) of the title compound.

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, 1,9-Dibromononane, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; ALMIRALL, S.A.; PRAT QUINONES, Maria; FONQUERNA POU, Silvia; PUIG DURAN, Carlos; LUMERAS AMADOR, Wenceslao; AIGUADE BOSCH, Jose; CATURLA JAVALOYES, Juan Francisco; WO2011/141180; (2011); A1;,
Bromide – Wikipedia,
bromide – Wiktionary

Synthetic Route of 69321-60-4, 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 69321-60-4 as follows.

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 mL). 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 mL). The filtrate was diluted with ethyl acetate (200 mL) and washed with water (40 mL), saturated aqueous sodium bicarbonate (40 mL) and brine (40 mL). 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, 1H, J = 8.1 Hz), 4.83 (s, 2H).

According to the analysis of related databases, 69321-60-4, the application of this compound in the production field has become more and more popular.

Reference:
Patent; GILEAD CONNECTICUT, INC.; GENENTECH, INC.; CURRIE, Kevin S.; WANG, Xiaojing; YOUNG, Wendy, B.; WO2012/30990; (2012); A1;,
Bromide – Wikipedia,
bromide – Wiktionary