Category: 18469-37-9

These common heterocyclic compound, 18469-37-9, name is 4-Bromo-N,N-dimethylbenzamide, 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. Computed Properties of C9H10BrNO

Example 23 Reduction of N,N-dimethyl-4-bromobenzamide A 20-mL eggplant flask equipped with a three-way cock and a magnetic stirrer was heat dried while pumping to a vacuum of 5 Pa before its interior was purged with argon atmosphere. Into the flask, iron complex A (1.0 mg, 0.002 mmol) was admitted as catalyst and dissolved in toluene (0.5 mL). To the solution, 1,2-bis(dimethylsilyl)benzene (475 muL) was added through a syringe, and N,N-dimethyl-4-bromobenzamide (228 mg, 1.0 mmol) was added. The solution was stirred at 100 C. for 30 minutes. Toluene was distilled off in vacuum. The crude product was purified by silica gel-packed column chromatography using hexane/ethyl acetate (20/1) as developing solvent, obtaining N,N-dimethyl-4-bromobenzylamine (184 mg, 0.86 mmol, 86%).

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

Reference:
Patent; Shin-Etsu Chemical Co., Ltd.; Kyushu University, National University Corporation; NAGASHIMA, Hideo; SUNADA, Yusuke; TSUTSUMI, Hironori; HASHIMOTO, Toru; SAKUTA, Koji; (24 pag.)US2016/23196; (2016); A1;,
Amide – Wikipedia,
Amide – an overview | ScienceDirect Topics

Adding a certain compound to certain chemical reactions, such as: 18469-37-9, name is 4-Bromo-N,N-dimethylbenzamide, belongs to amides-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 18469-37-9, SDS of cas: 18469-37-9

N,N-dimethyl-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzamide (0243) To a solution of 4-bromo-N,N-dimethylbenzamide (11.0 g, 48.23 mmol) in dioxane (300 mL) were added 4,4,5,5-tetramethyl-2-(tetramethyl-1,3,2-dioxaborolan-2-yl)-1,3,2-dioxaborolane (14.7 g, 57.89 mmol), Pd(dppf)Cl2 (3.5 g, 4.78 mmol) and potassium acetate (14.2 g, 144.69 mmol) at room temperature. The resulting mixture was stirred for 16 h at 100 C. The reaction mixture was cooled to room temperature and the resulting solid was removed by filtration. The filtrate was concentrated under reduced pressure and the resulting residue was purified by flash chromatography eluting with EtOAc in hexane (0% to 40% gradient) to yield N,N-dimethyl-4-(tetramethyl-1,3,2-dioxaborolan-2-yl)benzamide as orange solid (10.0 g, 70%). MS: m/z=276.0 [M+H]+.

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

Reference:
Patent; Merck Patent GmbH; SHERER, Brian A.; KARRA, Srinivasa; XIAO, Yufang; (407 pag.)US2016/376283; (2016); A1;,
Amide – Wikipedia,
Amide – an overview | ScienceDirect Topics

Adding a certain compound to certain chemical reactions, such as: 18469-37-9, name is 4-Bromo-N,N-dimethylbenzamide, belongs to amides-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 18469-37-9, SDS of cas: 18469-37-9

N,N-dimethyl-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzamide (0243) To a solution of 4-bromo-N,N-dimethylbenzamide (11.0 g, 48.23 mmol) in dioxane (300 mL) were added 4,4,5,5-tetramethyl-2-(tetramethyl-1,3,2-dioxaborolan-2-yl)-1,3,2-dioxaborolane (14.7 g, 57.89 mmol), Pd(dppf)Cl2 (3.5 g, 4.78 mmol) and potassium acetate (14.2 g, 144.69 mmol) at room temperature. The resulting mixture was stirred for 16 h at 100 C. The reaction mixture was cooled to room temperature and the resulting solid was removed by filtration. The filtrate was concentrated under reduced pressure and the resulting residue was purified by flash chromatography eluting with EtOAc in hexane (0% to 40% gradient) to yield N,N-dimethyl-4-(tetramethyl-1,3,2-dioxaborolan-2-yl)benzamide as orange solid (10.0 g, 70%). MS: m/z=276.0 [M+H]+.

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

Reference:
Patent; Merck Patent GmbH; SHERER, Brian A.; KARRA, Srinivasa; XIAO, Yufang; (407 pag.)US2016/376283; (2016); A1;,
Amide – Wikipedia,
Amide – an overview | ScienceDirect Topics

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 18469-37-9 as follows. COA of Formula: C9H10BrNO

General procedure: An 8.0 mL screw-cap vial containing a stirring bar was charged with [Ni(dMeObpy)(H 2 O) 2 (Br) 2 ] (8.5 mg, 0.018 mmol, 6 mol %), [[Ir{dF(CF 3 ) 2 ppy} 2 (bpy)]PF 6 ] (9.0 mg, 0.009 mmol, 3 mol %), amide (0.36 mmol, 1.2 equiv), aryl bromide (if solid) (0.3 mmol, 1.0 equiv) and Bu 4 N[OP(O)(OBu) 2 ] (338.8 mg, 0.75 mmol, 2.5 equiv). Next, the vial was closed, and three vacuum/argon cycles were carried out. Under inert atmosphere, a 2:1 mixture of dry t-BuOH/PhCF 3 was added (6.0 mL, 0.05 M) followed by addition of the aryl bromide (if liquid). After further sealing with Parafilm, the reaction was placed in the blue LED bay and stirred at rt until completion (a fan was added to disperse any heat coming from the blue LEDs). When completed, the reactions were taken to dryness and purified by column chromatography using an automated system (hexanes/EtOAc gradient), delivering the corresponding pure product.

According to the analysis of related databases, 18469-37-9, the application of this compound in the production field has become more and more popular.

Reference:
Article; Zheng, Shuai; Gutierrez-Bonet, Alvaro; Molander, Gary A.; Chem; vol. 5; 2; (2019); p. 339 – 352;,
Amide – Wikipedia,
Amide – an overview | ScienceDirect Topics