Category: 553-94-6

553-94-6, These common heterocyclic compound, 553-94-6, name is 2,5-Dimethylbromobenzene, 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: In the first step,reference solution (CPd=0.5¡Á10-4mmol/mL,CLigand=1.0¡Á10-4mmol/mL) was prepared. A single-neckedground tube (rinner=1.1 cm, L=17.5 cm) was equipped with a magnetic stirbar. 0.5 mmol of aryl halides, 0.75 mmol of phenyl boronic acid and 1 mmol basewere added into the tube under atmospheric condition. Then, appropriate amountof reference solution and solventwere added into the tube. The reaction mixture was stirredat the pre-arranged temperature for appropriate reaction time in oil bath. Afterthe reaction was completed, 3 mL water was added, and the mixture was extractedwith EtOAc(10 mL¡Á4). Then the organic phase was dried with Na2SO4and concentrated under reduced pressure. The residue was then purified by columnchromatography on silica gel. The pure product was obtained and was analyzed by1H NMR spectroscopy.

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 553-94-6.

Reference:
Article; Liu, Haiyang; Liu, Hailong; Li, Ruixiang; Chen, Hua; Tetrahedron Letters; vol. 55; 2; (2014); p. 415 – 418;,
Bromide – Wikipedia,
bromide – Wiktionary

553-94-6, Name is 2,5-Dimethylbromobenzene, 553-94-6, belongs to bromides-buliding-blocks compound, is considered to be a conventional heterocyclic compound, which is widely used in drug synthesis. The chemical synthesis route is as follows.

Add 15 mL of solvent dichloromethane to a 100 mL round bottom flask and weigh 3.0 g (16.21 mmol)2,5-Dimethylbromobenzene was added to a round bottom flask containing dichloromethane to make them mutually soluble, put into a stir bar, and stirred under ice water bath; 10 mL of dichloromethane was added to a 100 mL beaker, and 3.240 g was quickly weighed. (24.32 mmol) anhydrous aluminum chloride powder was added to a beaker containing dichloromethane, 2.36 g (27.56 mmol) of acetyl chloride was weighed into a beaker, and stirred with a glass rod to completely dissolve anhydrous aluminum trichloride. After dissolving, it was transferred to a constant pressure funnel, and then slowly and continuously added dropwise to the above 2,5-dimethylbromobenzene solution, and the reaction was stirred under an ice water bath condition; after the dropwise addition, the ice water bath was stirred for 1 hour, and the ice water bath was removed. The reaction was stirred at room temperature for 15 h; after the reaction was over, the burgundy solution obtained by the reaction was slowly added to a beaker containing 300 mL of cold water, and continuously stirred with a glass rod until the solution turned from burgundy to yellowish, and after cooling, Dichloromethane extraction (extraction 2 times, once with 100 mL), the lower layer of methylene chloride was retained, poured into a 500 mL beaker, dried over anhydrous sodium sulfate for 5 h, dried and filtered, and then evaporated. The solvent is removed, and the crude product is added. 100mL round bottom flask was added n-hexaneRecrystallization. The crude product was crystallized to give 2.76 g of white crystals, yield 75%.

Statistics shows that 2,5-Dimethylbromobenzene is playing an increasingly important role. we look forward to future research findings about 553-94-6.

Reference:
Patent; Heilongjiang University; Li Hongfeng; Wang Cheng; Sun Zhiyao; Sun Longjiang; Zheng Rongrong; Ma Dongge; Guo Dechao; Cui Guofeng; Yan Pengfei; (24 pag.)CN109096084; (2018); A;,
Bromide – Wikipedia,
bromide – Wiktionary

A common heterocyclic compound, 553-94-6, name is 2,5-Dimethylbromobenzene, molecular formula is C8H9Br, 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. 553-94-6.

1) Add 1 mol of 2-bromo-p-xylene or chloroacetyl chloride to the reaction kettle.The catalyst and DMSO were heated to 100 C under stirring for 5 h.Then a mixture of sodium sulfite and water was added dropwise to control the dropping time to 45 min.After the completion of the dropwise addition, the reaction temperature was raised to 135 C, and the reaction was continued for 7.5 h; The ratio of 2-bromo-p-xylene to chloroacetyl chloride is 1:1.14,The ratio of 2-bromo-p-xylene to catalyst is 1:0.07, and the ratio of 2-bromo-p-xylene to DMSO is 1g: 13ml.The ratio of 2-bromo-p-xylene to sodium sulfite was 1:1.18, and the ratio of sodium sulfite to water was 1:4.5. The preparation process of the catalyst is: Mix ruthenium oxide and 10% palladium carbon in a weight ratio of 1:20. Then soaked in 4% concentration of hydrochloric acid for 6 minutes,Then, a solid was obtained by filtration, and the solid was washed and then placed at 280 C for 2.5 h to obtain a catalyst. 2) cooling the system, filtering to remove insoluble matter to obtain a filtrate, and adding the filtrate to about 5 volumes of water.Then, the filtrate is added twice the volume of toluene, and the layer is allowed to stand, and the organic phase is washed with water.After drying with anhydrous sodium sulfate,Concentration gave the product in a molar yield of 98.1% and a HPLC purity of 97.5%.

The synthetic route of 2,5-Dimethylbromobenzene has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Shandong Nong Pharmaceutical Xue Institute; Jinan Kehai Co., Ltd.; Fu Hongxin; Yang Chaohui; Wang Ling; (6 pag.)CN109369378; (2019); A;,
Bromide – Wikipedia,
bromide – Wiktionary