Category: bromides-buliding-blocks

Electric Literature of 74586-53-1, The chemical industry reduces the impact on the environment during synthesis 74586-53-1, name is 3-Bromo-5-methylaniline, I believe this compound will play a more active role in future production and life.

To a stirring solution of 3-bromo-5-methylaniline (5.00 g, 26.9 mmol) in THF (100 mL) was added K2CO3 (11.14 g, 81 mmol) followed by 2-chloroethyl chloroformate (4.16 mL, 40.3 mmol) and the resulting reaction mixture was refluxed for 4 h. The reaction mixture was cooled to ambient temperature, diluted with 5% NaHCO3 solution (100 mL) and extracted with ethyl acetate (2 x 100 mL). The combined organic layers were washed with brine (50 mL), dried over anhydrous sodium sulfate and evaporated under reduced pressure to obtain Intermediate 76A (7.00 g, 89.00%) as a white solid. 1H NMR (300 MHz, DMSO-d6) G^ppm 2.25 (s, 3 H), 3.81 – 3.95 (m, 2 H), 4.32 – 4.42 (m, 2 H), 7.04 (s, 1 H), 7.26 (s, 1 H), 7.55 (s, 1 H), 9.96 (s, 1 H). LCMS (Method-D ): retention time 2.99 min, [M+H] 291.0.

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, 3-Bromo-5-methylaniline, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; BRISTOL-MYERS SQUIBB COMPANY; YADAV, Navnath Dnyanoba; BHIDE, Rajeev S.; BORA, Rajesh Onkardas; GUNAGA, Prashantha; PANDA, Manoranjan; PRIESTLEY, Eldon Scott; RICHTER, Jeremy; (444 pag.)WO2018/222795; (2018); 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., COA of Formula: C7H5BrF3N

Production Example 62N- [3-{2- [4- (hydrazinocarbonylmethyl) phenyl] ethyl}-2-(trifluoromethyl) phenyl] acetamide hydrochlorideUsing N7 [3-bromo-5- (trifluoromethyl) phenyl] acetamide obtained by treating 3-bromo-5- (trifluoromethyl) aniline with acetic anhydride as a starting material, the title compound was synthesized by a method similar to Production Example 1, steps 4 – 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:
Patent; R-tech Ueno, Ltd.; WO2009/145360; (2009); A1;,
Bromide – Wikipedia,
bromide – Wiktionary

Synthetic Route of 142808-15-9, 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. 142808-15-9 name is 4-Bromo-2-fluorobenzotrifluoride, 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.

Example 28 Preparation of 1-bromo-3-fluoro-2-methyl-4-(trifluoromethyl)benzene To a stirred solution of bis(isopropyl)amine (1.383 mL, 9.87 mmol) in THF (27.4 mL) at -78 C. was added n-butyllithium (3.62 mL, 9.05 mmol). The resulting pale yellow solution was stirred at -78 C. for 15 min, warmed to 0 C. for 15 min, then recooled to -78 C. for 15 min. 4-Bromo-2-fluoro-1-(trifluoromethyl)benzene (2 g, 8.23 mmol) was then added, and the resulting solution was stirred at -78 C. for 2 h. Iodomethane (0.512 mL, 8.22 mumol) was then added. The solution was allowed to slowly warm to room temperature (rt) and stirred overnight. The reaction mixture was diluted with 0.1 M hydrochloric acid (HCl) and extracted with dichloromethane. The combined organic layers were dried over MgSO4, filtered, and concentrated in vacuo. The crude brown residue was purified via flash chromatography on silica (5-30% ethyl acetate (EtOAc)/Hexanes) to yield the title compound as a clear oil (1.7 g, 80%): 1H NMR (400 MHz, CDCl3) delta 7.57-7.41 (m, 1H), 7.32-7.26 (m, 1H), 2.41 (dd, J=10.0, 8.3 Hz, 3H); 19F NMR (376 MHz, CDCl3) delta -61.2, -105.7, -108.1; IR (thin film) 2177, 1319 cm-1.

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

Reference:
Patent; Dow AgroSciences LLC; ECKELBARGER, Joseph D.; EPP, Jeffrey B.; FISCHER, Lindsey G.; GIAMPIETRO, Natalie C.; KISTER, Jeremy; PETKUS, Jeffrey; ROTH, Joshua; SATCHIVI, Norbert M.; SCHMITZER, Paul R.; SIDDALL, Thomas L.; YERKES, Carla N.; US2014/274703; (2014); A1;,
Bromide – Wikipedia,
bromide – Wiktionary

Synthetic Route of 393-37-3, A common heterocyclic compound, 393-37-3, name is 5-Bromo-2-fluorobenzotrifluoride, molecular formula is C7H3BrF4, 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 a solution of 4-bromo- 1 -fluoro-2-(trifluorom ethyl )benzene (5.0 g, 20.5 mmol, 2.9 mL) in THF (50.0 mL) was added LDA (2 M, 13.3 mL) at -78C. The mixture was stirred at – 78C for 1 hr. Then DMF (1.8 g, 24.6 mmol, 1.9 mL) was added and stirred for 1 h at -78C. The mixture was poured into Sat H4CI (20.0 mL) and extracted with ethyl acetate (20.0 mL chi 3). The combined organic layers were washed with brine (20.0 mL chi 3), dried over Na2S04, filtered and concentrated under reduced pressure to give a residue. The residue was purified by column chromatography (S1O2) to afford 5-bromo-2-fluoro-3-(trifluoromethyl)benzaldehyde (4 g, 14.7 mmol, 71.7% yield). MR (CHLOROFORM-c , 400 MHz): delta 10.35 (s, 1H), 8.19 (dd, 7= 2.5, 5.4 Hz, 1H), 7.98 (dd, 7= 2.1, 6.1 Hz, 1H)

The synthetic route of 393-37-3 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; QUENTIS THERAPEUTICS, INC.; VACCA, Joseph P.; LI, Dansu; BETTIGOLE, Sarah; (214 pag.)WO2019/94641; (2019); A1;,
Bromide – Wikipedia,
bromide – Wiktionary

Adding a certain compound to certain chemical reactions, such as: 112734-22-2, name is (4-Bromo-2-fluorophenyl)methanamine, 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 112734-22-2, Product Details of 112734-22-2

Step 1 : 4-Bromo-2-fluorobenzylamine (924 mg, 4.53 mmol) was dissolved in pyridine and ethane sulfonyl chloride (0.82 mL, 8.60 mmol) was added to the solution at O C. The mixture was stirred for 1 h at O C. Then, the mixture was quenched with 1 N HCl and extracted with ethyl acetate (EtOAc). Drying (MgSO4) and evaporation of the ethyl acetate followed and the residue was purified by CC (eluent EtOAc/n-hexane) to yield N-(4-bromo-2- fluorobenzyl)ethanesulfonamide in pure form (1 .06 g, 79 %).

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:
Patent; GRUeNENTHAL GMBH; FRANK, Robert; CHRISTOPH, Thomas; DAMANN, Nils; LESCH, Bernhard; BAHRENBERG, Gregor; SAUNDERS, Derek John; STOCKHAUSEN, Hannelore; KIM, Yong-Soo; KIM, Myeong-Seop; LEE, Jeewoo; WO2013/68462; (2013); A1;,
Bromide – Wikipedia,
bromide – Wiktionary

Adding a certain compound to certain chemical reactions, such as: 656-64-4, name is 3-Bromo-4-fluoroaniline, 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 656-64-4, Application In Synthesis of 3-Bromo-4-fluoroaniline

General procedure: A stirred mixture of compound 5 (0.23 g, 0.001 mol), EDCI (0.23 g, 0.0012 mol), HOBt (0.16 g,0.0012 mol), aniline or aniline derivative (0.001 mol), and 20 mL DMF was reacted at room temperature overnight, and then 40 mL water was added and stirred for a quarter, before the crude was filtered and washed twice with water. The anticipated product was purified by column chromatography on silicagel using petroleum ether/ethyl acetate (2/1, volume ratio) as the eluent to afford the target compound.

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; Deng, Xinshan; Tan, Xiaoyu; An, Tiantian; Ma, Qingqing; Jin, Zhe; Wang, Ce; Meng, Qingguo; Hu, Chun; Molecules; vol. 24; 4; (2019);,
Bromide – Wikipedia,
bromide – Wiktionary

Synthetic Route of 202865-83-6, These common heterocyclic compound, 202865-83-6, name is 1-Bromo-3-fluoro-5-methylbenzene, 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.

Step 1: Preparation of 8-(3-fluoro-5-methyl-phenyl)-1,4-dioxa-8-azaspiro[4.5]decane A mixture of 1,4-dioxa-8-azaspiro[4.5]decane hydrochloride (4.0 g, 22.3 mmol), 1-bromo- 3-fluoro-5-methylbenzene (5.05 g, 26.7 mmol), Pd2(dba)3 (408 mg, 445 mumol), Ruphos (416 mg, 891 mumol) and Cs2CO3 (18.1 g, 55.7 mmol) in toluene (50 mL) was heated with stirring at 120 C for 15 hrs. The resulting reaction mixture was filtered through celite and the filtrate was concentrated in vacuo. The residue was purified by flash chromatography to give 8-(3-fluoro-5- methyl-phenyl)-1,4-dioxa-8-azaspiro[4.5]decane (5.0g) as a yellow oil.

Statistics shows that 1-Bromo-3-fluoro-5-methylbenzene is playing an increasingly important role. we look forward to future research findings about 202865-83-6.

Reference:
Patent; F. HOFFMANN-LA ROCHE AG; HOFFMANN-LA ROCHE INC.; CHENG, Zhanling; HAN, Xingchun; JIANG, Min; WANG, Jianhua; WANG, Min; WANG, Yongguang; YANG, Song; (319 pag.)WO2016/177655; (2016); A1;,
Bromide – Wikipedia,
bromide – Wiktionary

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 452-63-1 as follows. Recommanded Product: 452-63-1

A screw-capped vial (8 mL) was charged with compound 538 (100 mg, 0.37 MMOL) in 1,4-dioxane (2 mL), 2-bromo-5-fluoro-toluene (55 LULL, 0.44 MMOL), CS2C03 (169 mg, 0.52 MMOL), PD2 (dba) 3 (9 mg, 0.009 MMOL), and rac-BINAP (9 mg, 0.014 MMOL). The tube was capped with a rubber septum, flushed with argon for 5 min, and then stirred at 100 C for 18 h. The reaction mixture was allowed to cool to room temperature, and then poured into a mixture of water and EtOAc. The aqueous phase was extracted twice with more EtOAc. The combined organic phases were washed with brine, dried (MgS04), filtered and concentrated in vacuo. The crude product was purified by chromatography eluting with EtOAc/petroleum ether 1: 3 to afford the title compound as light brown oil.

According to the analysis of related databases, 452-63-1, the application of this compound in the production field has become more and more popular.

Reference:
Patent; LEO PHARMA A/S; WO2005/9940; (2005); A1;,
Bromide – Wikipedia,
bromide – Wiktionary

Reference of 445-02-3, 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. 445-02-3 name is 4-Bromo-2-(trifluoromethyl)aniline, 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.

2-Amino-5-bromobenzotrifluoride 9a (1.1 g, 4.58 mmol), 1,2,3-propanetriol (1.69 g, 18.3 mmol) and iron (II) sulfate heptahydrate (204 mg, 0.73 mmol) were added to a reaction flask. The reaction solution was cooled to 0C, and added dropwise with 0.8 mL of sulfuric acid. After completion of the addition, the reaction solution was heated to 120C, and stirred for 4 hours. The reaction was stopped, and the reaction solution was cooled to room temperature, added with 20 mL of water, and extracted with ethyl acetate (30 mL×3). The organic phases were combined, and concentrated under reduced pressure. The residue was purified by CombiFlash rapid preparation instrument with elution system B to obtain the title product 9b (0.9 g), yield: 71.4%. MS m/z (ESI): 210.6 [M+1].

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

Reference:
Patent; Jiangsu Hengrui Medicine Co. Ltd.; Shanghai Hengrui Pharmaceutical Co., Ltd.; LU, Biao; ZHANG, Junzhen; JIN, Fangfang; HE, Feng; TAO, Weikang; EP3569596; (2019); A1;,
Bromide – Wikipedia,
bromide – Wiktionary

Electric Literature of 134168-97-1,Some common heterocyclic compound, 134168-97-1, name is 3-Bromo-5-fluoroaniline, molecular formula is C6H5BrFN, 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 solution of 3-bromo-5-fluoroaniline (CAS 134168-97-1) (380 mg, 2.0 mmol) and 1-(2-chloroethyl)pyrrolidine (CAS 505041-9) (380 mg, 2.2 mmol) in NMP (20 mL) was heated to 120 C. overnight. The solution was diluted with EtOAc (100 mL) and washed with saturated Na2CO3 aqueous solution (3*40 mL). The combined organic layer were dried over Na2SO4, concentrated and purified by prep-TLC (DCM: MeOH=10:1) to give the titled product (290 mg, 50%). LCMS (0-60 AB), RT=1.076 min, M+H, 289.0

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-fluoroaniline, its application will become more common.

Reference:
Patent; Chen, Huifen; Crawford, Terry; Harris, Seth F.; Magnuson, Steven R.; Ndubaku, Chudi; Wang, Lan; US2013/324516; (2013); A1;,
Bromide – Wikipedia,
bromide – Wiktionary