Tag: M.W=100-200

Synthetic Route of 55289-36-6, 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 55289-36-6 as follows.

A mixture of 3-bromo-2-methylaniline (10 mL, 60.52 mmol), chloral hydrate (14.86 g, 89.86 mmol) and anhydrous Na2S04 (94.56 g, 665.74 mmol) in hydrochloric acid (6.4 mL, 21 1.24 mmol) and H2O (700 mL) was stirred vigorously at room temperature overnight. To the resulting mixture, hydroxylamine hydrochloride (5.86 g, 84.26 mmol) was added and the mixture was heated to reflux overnight. The reaction mixture was ice cooled, and the resulting precipitate was collected by vacuum filtration and washed copiously with H2O and dried under suction. The precipitate was re-dissolved in EtOAc (-500 mL) and washed with H2O (300 mL) and brine (300 mL) then dried over MgS04. The resulting filtrate was removed in vacuo to give 6-bromo-7-methyl-indoline-2,3-dione as a dark brown solid in quantitative yield, which was used directly in the next step without further purification. LC-MS 238.5/240.5 [M+H]+; RT 1.84 min

According to the analysis of related databases, 55289-36-6, the application of this compound in the production field has become more and more popular.

Reference:
Patent; REDX PHARMA PLC; STOKES, Neil; (163 pag.)WO2017/46603; (2017); A1;,
Bromide – Wikipedia,
bromide – Wiktionary

Adding a certain compound to certain chemical reactions, such as: 65896-11-9, name is 2-Bromo-6-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 65896-11-9, Quality Control of 2-Bromo-6-fluoroaniline

[0676] 2-Propylzinc bromide (0.50 M in THF, 16 mL, 7.9 mmol, Sigma-Aldrich Corporation, St. Louis, MO, USA) was added to a stirred mixture of 2-bromo-6-fluoroaniline (1.00 g, 5.26 mmol, Acros, Geel, Belgium), palladium (II) acetate (0.059 g, 0.263 mmol), and 2-dicyclohexylphosphino-2′,6′-dimethylamino-1,1′-biphenyl (0.230 g, 0.526 mmol, Strem Chemicals, Newburyport, MA) in THF (10 mL), and the resulting mixture was stirred under Ar(g) in a sealed vial at rt for 3 h. The reaction mixture was then diluted with satd. aq. ammonium chloride and extracted with EtOAc. The organic extract was then washed with brine, dried over MgSO4, filtered, and concentrated in vacuo. Chromatographic purification of the residue (silica gel, eluent: 0-25% EtOAc in heptane) gave 2-fluoro-6-isopropylaniline as a yellow oil (Intermediate I-26, 618 mg, 4.03 mmol, 77 % yield).1H NMR (400 MHz, CDCl3) d ppm 6.92 (1H, d, J=7.88 Hz) 6.86 (1H, ddd, J=10.73, 8.14, 1.24 Hz) 6.69 (1H, td, J=7.88, 5.60 Hz) 3.70 (2 H, br s) 2.92 (1H, spt, J=6.84 Hz) 1.26 (6 H, d, J=6.84 Hz). m/z (ESI, +ve ion): 154.1 (M+H)+.

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; AMGEN INC.; ALLEN, John Gordon; ALLEN, Jennifer Rebecca; MINATTI, Ana Elena; XUE, Qiufen; WURZ, Ryan Paul; TEGLEY, Christopher M.; PICKRELL, Alexander J.; NGUYEN, Thomas T.; MA, Vu Van; LOPEZ, Patricia; LIU, Longbin; KOPECKY, David John; FROHN, Michael J.; CHEN, Ning; CHEN, Jian Jeffrey; SIEGMUND, Aaron C.; AMEGADZIE, Albert; TAMAYO, Nuria A.; BOOKER, Shon; GOODMAN, Clifford; WALTON, Mary; NISHIMURA, Nobuko; SHIN, Youngsook; LOW, Jonathan D.; CEE, Victor J.; REED, Anthony B.; WANG, Hui-Ling; LANMAN, Brian Alan; (738 pag.)WO2019/213516; (2019); A1;,
Bromide – Wikipedia,
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Application of 348-57-2, 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. 348-57-2, name is 1-Bromo-2,4-difluorobenzene, This compound has unique chemical properties. The synthetic route is as follows.

A total of 1.6 g of 1-bromo-2,4-difluorobenzene was suspended in 8.29 ml of sulfuric acid, and 1.62 g of N-bromosuccinimide was added under ice-cooling. After stirring at room temperature for 17 hours, the reaction mixture was poured onto ice-water and extracted with ethyl acetate. The resulting organic layer was washed with saturated aqueous sodium hydrogencarbonate solution and brine, dried over magnesium sulfate and the solvent was evaporated. The residue was purified and separated by silica gel column chromatography (hexane), to give 2.18 g of the title compound as a pale yellow oil.1H-NMR ( 400MHz, CDCl3 ) d 6.99 ( 1H, t, J = 8. 0 Hz ), 7.77 ( 1H, t, J = 6. 8 Hz )

The chemical industry reduces the impact on the environment during synthesis 1-Bromo-2,4-difluorobenzene. I believe this compound will play a more active role in future production and life.

Reference:
Patent; Eisai Co., Ltd.; EP1380576; (2004); A1;,
Bromide – Wikipedia,
bromide – Wiktionary

Synthetic Route of 626-88-0, The chemical industry reduces the impact on the environment during synthesis 626-88-0, name is 1-Bromo-4-methylpentane, I believe this compound will play a more active role in future production and life.

Step 1. Preparaion of 1-Chloro-8-methyl-4-nonanone To the Grignard reagent prepared from a mixture of 1-bromo-4-methylpentane (200.00 g.; 1.21 mole) and magnesium (29.43 g.; 1.21 mole) in ether (800 ml.) is added, dropwise during one hour, 4-chlorobutyronitrile (125.30 g.; 1.21 mole). Stirring is continued for an additional one hour. The reaction mixture is poured into a mixture of finely crushed ice (800 g.) and concentrated hydrochloric acid (600 ml.). The ether layer is separated quickly and discarded. The aqueous layer is heated on a steam bath for one hour to hydrolyze the intermediate imine and cause the separation of the ketone as an oil. After cooling, the oil is extracted with ether and the combined extracts are washed with saturated sodium chloride solution and dried over anhydrous sodium sulfate. The solvent is removed under vacuum and the residual oil is distilled to give 23.3 g. (10%) of colorless oil, b.p. 121-122/15 mm.; pmr (CDCl3)delta 0.89 (6H,d), 3.57 (2H,t CH2 Cl). Anal. Calcd. for C10 H19 ClO: C, 62.98; H, 10.04. Found: C, 62.86; H, 10.20.

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

Reference:
Patent; Merck & Co., Inc.; US4055597; (1977); A;,
Bromide – Wikipedia,
bromide – Wiktionary

Adding a certain compound to certain chemical reactions, such as: 17247-58-4, name is (Bromomethyl)cyclobutane, 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 17247-58-4, Formula: C5H9Br

To a solution of deprotected phenol derivative 20 (0.3 g, 0.571 mmol) in dimethylformamide (10 mL) was added sodium hydride (50 mg, 2.083 mmol) and K2CO3 (0.8 g, 5.79 mmol) at 0 C, stirred for 15 min, followed by addition of (bromomethyl)cyclobutane (90 mg, 0.602 mmol). After completion of addition, ice-bath was removed and the reaction mixture was stirred at rt for 4 h. Upon completion of the reaction, mixture was poured into ice-water (250 mL) and extracted with ethyl acetate (3 x 30 mL). The combined organic layer was washed with saturated aq. NaHCO3 and brine, dried over Na2SO4 and concentrated in vacuo to obtain the crude product. The crude product was purified using column chromatography (n-hexane/EtOAc 60:40) to obtain 6-O-(cyclobutyl)methyl derivative 39 (0.27 g, 75%) TLC: Rf = 0.64 (n-hexane/EtOAc 50:50). m.p. = 145-147 C. 1H-NMR (400 MHz, CDCl3) delta 0.33 (d, J = 4.4 Hz, 4H), 0.56 (d, J = 7.8 Hz, 2H), 1.05 (t, J = 7.1 Hz, 3H), 1.20 (t, J = 7.4 Hz, 1H), 1.27 (t, J = 7.5 Hz, 3H), 2.65 (q, J = 7.5 Hz, 2H), 3.89 (d, J = 6.4 Hz, 2H), 3.99 (s, 2H), 4.24 (q, J = 7.1 Hz, 2H), 5.19 (s, 2H), 5.85 (s, 2H), 6.21 (s, 1H), 6.74 (s, 1H), 7.08 (d, J = 9.4 Hz, 1H), 7.11 (dd, J = 9.3 Hz, 1H), 7.31 (t, J = 7.7 Hz, 1H), 7.60 (d, J = 7.6 Hz, 1H), 7.82 (s, 1H), 7.84 (d, J = 8.9 Hz, 1H), 7.99 (s, 1H).

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, (Bromomethyl)cyclobutane, other downstream synthetic routes, hurry up and to see.

Reference:
Article; Khadtare, Nikhil; Stephani, Ralph; Korlipara, Vijaya; Bioorganic and Medicinal Chemistry Letters; vol. 27; 11; (2017); p. 2281 – 2285;,
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. 7073-94-1, name is 1-Bromo-2-isopropylbenzene, This compound has unique chemical properties. The synthetic route is as follows., Recommanded Product: 1-Bromo-2-isopropylbenzene

Step I: To a solution of 2-bromoisopropyl benzene (2.0 g, 10.0 mmole) in dry THF (20 mL), nBuLi (1.6 M in hexane), (6.9 mL, 11.05 mmole) was added at -78 C. and the mixture was stirred at same temperature for one hour. DMF (0.9 g, 12.0 mmole) was added and the mixture was stirred at -78 C. for half an hour then allowed to stir at 0 C. for 15 min. The reaction mixture was diluted with saturated aqueous ammonium chloride (10 mL) and extracted with EtOAc (3*30 mL). The organic layers were combined and washed with brine, dried over sodium sulfate, and concentrated to yield 2-isopropyl benzaldehyde (1.4 g).

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 7073-94-1.

Reference:
Patent; NOVARTIS AG; US2011/171159; (2011); A1;,
Bromide – Wikipedia,
bromide – Wiktionary

Related Products of 4117-09-3,Some common heterocyclic compound, 4117-09-3, name is 7-Bromo-1-heptene, molecular formula is C7H13Br, 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 alkyl bromide (1.0 equiv) was added to a solution of mercaptoaceticacid (1.0 equiv) in methanol (10.0 mL) and the resultingsolution stirred. Then a solution of NaOH (2.0 equiv) in methanol(5.0 mL)was added slowly, and the final mixturewas stirred at roomtemperature or heated to reflux until absence of the alkyl bromide(checked by TLC). The reaction mixture was concentrated in vacuo,diluted with H2O, and neutralized with 1 N HCl. Then the obtainedreaction mixture was extracted with EtOAc. The combined organicfractions were washed with brine, dried with Na2SO4, and concentratedin vacuo. Purification of the crude residue by column chromatography(petroleum ether/EtOAc) afforded the title compound.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 7-Bromo-1-heptene, its application will become more common.

Reference:
Article; Chen, Ying; Wu, Bolin; Hao, Yameng; Liu, Yunqi; Zhang, Zhili; Tian, Chao; Ning, Xianling; Guo, Ying; Liu, Junyi; Wang, Xiaowei; European Journal of Medicinal Chemistry; vol. 171; (2019); p. 420 – 433;,
Bromide – Wikipedia,
bromide – Wiktionary

Related Products of 556-96-7, 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. 556-96-7 name is 1-Bromo-3,5-dimethylbenzene, 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.

I.2 Synthesis Methods and Characterization of the CompoundsI2.1 Bis(3,5-Dimethylphenyl)Phosphinic Acid 1-Bromo-3,5-dimethylbenzene (13.63 g, 71.44 mmol, 97%) is added dropwise at room temperature to magnesium turnings (1.74 g, 71.44 mmol) in anhydrous THF (80 mL). Once the magnesium has dissolved completely, a solution of N,N-dimethylphosphoryl dichloride N(Me)2P(O)Cl2 (4.33 mL, 35.72 mmol) in anhydrous THF (10 mL) is added dropwise. To remove the salt formed in the reaction, the reaction mixture, after two hours, is added to an ice-cooled ammonium chloride solution (30 g in 500 mL of water). In a distillation apparatus, the THF is subsequently removed and the residue is boiled with concentrated HCl (75 mL) at 80 C. The resulting white solid is dissolved in aqueous NaOH (5.4 g, 300 mL of water) and the aqueous phase is extracted twice with diethyl ether. The clear aqueous phase is acidified again by adding concentrated HCl, in order to precipitate the phosphinic acid as a white solid in 70% yield (6.81 g).

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

Reference:
Patent; BASF SE; KONINKLIJKE PHILIPS ELECTRONICS N.V.; OSRAM OPTO SEMICONDUCTORS GMBH; US2011/172423; (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. 1003-98-1, name is 2-Bromo-4-fluoroaniline, A new synthetic method of this compound is introduced below., Product Details of 1003-98-1

2-Bromo-4-fluoroaniline (0.54 g, 2.84 mmol) was dissolved in MeCN (14.21 ml). Ammonium thiocyanate (0.324 g, 4.26 mmol) was added to the reaction mixture followed by benzyltrimethylammonium tribromide (1.108 g, 2.84 mmol), and thereaction mixture was allowed to stir for 12 hours. The reaction mixture was diluted with saturated aqueous NaHCO3, and the solids were collected by suction filtration and washed with water to yield Intermediate 806A (0.700 g, 2.84 mmol, 100%). ?H NIVIR (4001V11{z, MeOH4) 7.41 (dd, J8.0, 2.5 Hz, 1H), 7.26 (dd, J8.9, 2.5 Hz, 1H). LC-MS. method H, RT = 0.81 mm, MS (ESI) m/z: 247/249 (M+H).

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; BRISTOL-MYERS SQUIBB COMPANY; ZHANG, Xiaojun; PRIESTLEY, Eldon Scott; BATES, J. Alex; HALPERN, Oz Scott; REZNIK, Samuel Kaye; RICHTER, Jeremy M.; (1137 pag.)WO2018/13774; (2018); A1;,
Bromide – Wikipedia,
bromide – Wiktionary

Application of 399-94-0,Some common heterocyclic compound, 399-94-0, name is 1-Bromo-2,5-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.

At -40C,Add 2.0 M isopropyl chloride to a solution of 2-bromo-1,4-difluorobenzene (186 g) in THF (1.0 L)Magnesium in THF (482 mL),And continue stirring at 5 C for 1 h.At -40C,A solution of tert-butyl 2-oxopyrrolidine-1-carboxylate (215.5 g) in THF (250 mL) was added dropwise to the above reaction mixture.And continue stirring at 10 C for 2 h.The reaction mixture was quenched with saturated ammonium chloride solution,Extract with ethyl acetate,Dry with anhydrous sodium sulfatefilter,And concentrate the filtrate under reduced pressure,The crude title compound was obtained (323.4 g),It is used directly in the next step without purification.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 1-Bromo-2,5-difluorobenzene, its application will become more common.

Reference:
Patent; Zhengda Tianqing Pharmaceutical Group Co., Ltd.; Beijing Sai Lintai Pharmaceutical Co., Ltd.; Lianyungang Runzhong Pharmaceutical Co., Ltd.; Zhu Li; Hu Yuandong; Dai Liguang; Yang Yanqing; Duan Xiaowei; Yang Zhao; Wu Wei; Sun Yinghui; Han Yongxin; Peng Yong; Luo Huiyan; Luo Hong; Yang Ling; Xu Hongjiang; Guo Meng; Zhong Zhaobo; Wang Shanchun; (102 pag.)CN108003161; (2018); A;,
Bromide – Wikipedia,
bromide – Wiktionary