Category: 90110-98-8

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. 90110-98-8, name is 3-Bromo-4-(hydroxymethyl)benzonitrile, A new synthetic method of this compound is introduced below., COA of Formula: C8H6BrNO

A solution of compound B (211 mg, 1.0 mmol) and triisopropyl borate (282 mg, 1.5 mmol) in anhydrous THF (10 mL) at N2 atmosphere was cooled to -78C. n- BuLi (0.9 mL, 2.25 mmol) was added dropwise at -78C. Then the mixture was allowed to warm to room temperature and stirr at room temperature for 1 h. The mixture was qunched with IN HCl and extracted with ethyl acetate (25 mL*3). The combined organic layers were washed with brine (20 mL), dried (Na2SO4) and concentrated under vacuum. The residue was purified by column chromatography (eluting with CH3OH and EtOAc =1 :1) on silica gel to give the desired compound C as a yellow solid (80 mg, 50 %).1H NMR (300 MHz, CDCl3): delta 9.50 (s, IH), 8.08 (s, IH), 7.83-7.92 (m, IH), 7.61-7.66 (m, IH), 5.06 (s, 2H). LC-MS: 160 (M + I)+.

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; ANACOR PHARMACEUTICALS, INC.; JACOBS, Robert; ORR, Matthew; WRING, Stephen; CHEN, Daitao; ZHOU, Huchen; DING, Dazhong; FENG, Yiqing; YE, Long; HERNANDEZ, Vincent, S.; ZHANG, Yong-Kang; PLATTNER, Jacob J.; WO2010/45503; (2010); A1;,
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

Electric Literature of 90110-98-8,Some common heterocyclic compound, 90110-98-8, name is 3-Bromo-4-(hydroxymethyl)benzonitrile, molecular formula is C8H6BrNO, 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.

LiAlH4 (34.0 mmol; 34.0 mL of a 1.0 M solution in THF) was cooled to 0 C using an ice bath then treated with MeOH (102 mmol; 26.4 mL of a 3.86 M solution in THF) dropwise over 5 min. The product of Part 3C (0.900 g, 4.24 mmol) was then added and the resulting solution warmed slowly to ambient temperature as the ice bath melted. After 16 h total reaction time, the solution was diluted with H2O (9.0 mL) and the resulting suspension filtered through a scintered glass funnel of medium porosity. The solids were exhaustively washed with H2O and Et2O then transferred to a separatory funnel and split. The aqueous layer was further washed with Et2O and EtOAc and the combined organic layers dried over Na2SO4, filtered and concentrated in vacuo to a yellow solid (0.591 g), which was used without further purification in the subsequent reaction.

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-4-(hydroxymethyl)benzonitrile, its application will become more common.

Reference:
Patent; LANTHEUS MEDICAL IMAGING, INC.; RADEKE, Heike, S.; CESATI, Richard, R.; PUROHIT, Ajay; HARRIS, Thomas, D.; ROBINSON, Simon, P.; YU, Ming; CASEBIER, David, S.; HU, Carol, Hui; BROEKEMA, Matthias; ONTHANK, David, C.; WO2013/36869; (2013); A2;,
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

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. 90110-98-8, name is 3-Bromo-4-(hydroxymethyl)benzonitrile, A new synthetic method of this compound is introduced below., Safety of 3-Bromo-4-(hydroxymethyl)benzonitrile

A solution of compound B (211 mg, 1.0 mmol) and triisopropyl borate (282 mg, 1.5 mmol) in anhydrous THF (10 mL) at N2 atmosphere was cooled to -78C. n- BuLi (0.9 mL, 2.25 mmol) was added dropwise at -78C. Then the mixture was allowed to warm to room temperature and stirr at room temperature for 1 h. The mixture was qunched with IN HCl and extracted with ethyl acetate (25 mL*3). The combined organic layers were washed with brine (20 mL), dried (Na2SO4) and concentrated under vacuum. The residue was purified by column chromatography (eluting with CH3OH and EtOAc =1 :1) on silica gel to give the desired compound C as a yellow solid (80 mg, 50 %).1H NMR (300 MHz, CDCl3): delta 9.50 (s, IH), 8.08 (s, IH), 7.83-7.92 (m, IH), 7.61-7.66 (m, IH), 5.06 (s, 2H). LC-MS: 160 (M + I)+.

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; ANACOR PHARMACEUTICALS, INC.; JACOBS, Robert; ORR, Matthew; WRING, Stephen; CHEN, Daitao; ZHOU, Huchen; DING, Dazhong; FENG, Yiqing; YE, Long; HERNANDEZ, Vincent, S.; ZHANG, Yong-Kang; PLATTNER, Jacob J.; WO2010/45503; (2010); A1;,
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

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 90110-98-8 as follows. Recommanded Product: 90110-98-8

1.4 (Z)-3-bromo-N’-hydroxy-4-hydroxymethyl benzamidine (1-3) Hydroxylamine hydrochloride (0.524 g, 7.54 mmol) and sodium bicarbonate (1.27 g, 15.08 mmol) were added successively to a solution of 3-bromo-4-hydroxymethyl benzonitrile (1-2, 0.80 g, 3.77 mmol) in methanol (120 mL) to obtain a suspension which was then heated to reflux for 5 hours. It was then cooled down to room temperature and filtered. The filter cake was washed with methanol (10 mL), and the filtrate was concentrated to obtain 3-bromo-N’-hydroxy-4-hydroxymethyl benzamidine which was a white crude product (1-3, 0.90 g, 97% yield), which was directly used in the next step. The molecular ion peak shown by liquid chromatography-mass spectrometry was: MS (ESI): m/z 245/247 [M+H]+.

According to the analysis of related databases, 90110-98-8, the application of this compound in the production field has become more and more popular.

Reference:
Patent; SUZHOU CONNECT BIOPHARMACEUTICALS, LTD.; ZHENG, Wei; PAN, Wubin; YANG, Xin; (47 pag.)EP3048103; (2016); A1;,
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts

Synthetic Route of 90110-98-8, 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. 90110-98-8, name is 3-Bromo-4-(hydroxymethyl)benzonitrile, This compound has unique chemical properties. The synthetic route is as follows.

At 0-10C, anhydrous ethanol (27 mL) was slowly added dropwise into a mixture of selenium powder (2.7 g, 34.2 mmol) and sodium borohydride (1.57 g, 41.5 mmol), then heated to room temperature and stirred for 30 min, and then added with pyridine solution (7.2 mL) containing 3-bromo-4-isopropylthiomethyl benzonitrile (63) (1.8 g, 8.49 mmol). The reaction solution was heated until reflux occurred, slowly added dropwise with 2M hydrochloric acid solution (18 mL) and then stirred under reflux for 1 h. A TLC analysis indicated that the reaction was completed. The solution was cooled to room temperature, added with a proper amount of water and then extracted with ethyl acetate (30 mL¡Á3). The organic phase was respectively washed with 2M hydrochloric acid (20 mL) and saturated saline solution (20 mL), and dried with anhydrous sodium sulfate. The solvent was removed by means of reduced pressure distillation, so as to obtain pink 3-bromo-4-hydroxymethyl selenobenzamide (64) (1.98 g), with a yield of 79.6%.

The chemical industry reduces the impact on the environment during synthesis 3-Bromo-4-(hydroxymethyl)benzonitrile. I believe this compound will play a more active role in future production and life.

Reference:
Patent; Atom Bioscience and Pharmaceutical Co. Ltd.; SHI, Dongfang; FU, Changjin; WU, Jie; LIU, Jun; EP2927219; (2015); A1;,
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts