Category: 20469-65-2

Some common heterocyclic compound, 20469-65-2, name is 1-Bromo-3,5-dimethoxybenzene, molecular formula is C8H9BrO2, 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. 20469-65-2

A mixture of 1-bromo-3,5-dimethoxy-benzene (9.6 g, 44 mmol), CuI (0.7 g, 3.6 mmol), NaI (13.3 g, 88 mmol) and MeNHCH2CH2NHMe (0.78 mL) in 1,4-dioxane (80 mL) was degassed and filled with nitrogen in a sealed tube. The reaction mixture was heated at 120 C. for 20 h. The mixture was cooled to room temperature. Water (100 mL) was added, and the mixture was extracted with ethyl acetate (2*60 mL). The organic layers were washed with brine (50 mL), dried over sodium sulfate, and concentrated to give the title compound (10 g, 86%).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 20469-65-2, its application will become more common.

Reference:
Patent; HINMAN, Andrew W.; Davis, Dana; Kheifets, Viktoria; US2014/256830; (2014); A1;,
Ether – Wikipedia,
Ether | (C2H5)2O – PubChem

20469-65-2, Adding a certain compound to certain chemical reactions, such as: 20469-65-2, name is 1-Bromo-3,5-dimethoxybenzene, belongs to ethers-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 20469-65-2.

the mixture 1-bromo-3,5-dimethoxybenzene 1c (6.51g, 30mmol), trimethylsilylacetylene (8.8g, 90mmol), bis (triphenylphosphine) palladium chloride (1.05g, 1.5mmol), cuprous iodide (0.56g, 3.0mmol), triethylamine (80 mL) and N, N-dimethylformamide (150 mL) were heated to 80 C. and stirred under nitrogen protection for 12 hours.The reaction mixture was cooled to room temperature, concentrated under reduced pressure, and the residue was purified by silica gel column chromatography (petroleum ether) to obtain the target product ((3,5-dimethoxyphenyl) ethynyl) trimethylsilane 1d (6.2 g, brown solid), yield: 88%.

According to the analysis of related databases, 20469-65-2, the application of this compound in the production field has become more and more popular.

Reference:
Patent; BEIJING TIANCHENG PHARMA CO., LTD.; CHEN, XIANGYANG; GAO, YINGXIANG; KONG, NORMAN XIANGLONG; (118 pag.)TW2019/38538; (2019); A;,
Ether – Wikipedia,
Ether | (C2H5)2O – PubChem

20469-65-2, Name is 1-Bromo-3,5-dimethoxybenzene, 20469-65-2, belongs to ethers-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.

Step 1: 5-bromobenzene-1,3-diol To a mixture of 1-bromo-3,5-dimethoxybenzene (15 g, 69.1 mmol) in dichloromethane (500 ml) at 0 00 was added BBr3 (14.37 ml, 152 mmol) dropwise over 5 minutes at 0 00. The reaction mixture was allowed to warm to room temperature andstirred for 5 hours. The reaction was then cooled to 0 00 and BBr3 (7.2 ml, 76 mmol) added dropwise. The reaction mixture was allowed to warm up to room temperature and stirred overnight. The reaction was again cooled to 0 00 and BBr3 (3.6 ml, 38 mmol) added dropwise. The reaction mixture was allowed to warm up to room temperature and stirred for 4 hours. The mixture was then poured slowly onto ice. When the ice melted,DCM (200 ml) was added and the layers separated. The aqueous was extracted with EtOAc (500 ml) and the layers separated. The combined organics were passed throughthrough a hydrophobic frit and concentrated. The residue was purified via flash chromatography (ISCO Combiflash Rf, 220 g column, 0-100 % ethyl acetate/hexanes) to give the title compound as a yellow oil (19.5 g, 70 % purity). MS (mlz) 189.0 (M).

Statistics shows that 1-Bromo-3,5-dimethoxybenzene is playing an increasingly important role. we look forward to future research findings about 20469-65-2.

Reference:
Patent; GLAXOSMITHKLINE INTELLECTUAL PROPERTY (NO.2) LIMITED; DOWDELL, Sarah E.; EIDAM, Hilary Schenck; ELBAN, Mark; FOX, Ryan Michael; HAMMOND, Marlys; HILFIKER, Mark A.; HOANG, Tram H.; KALLANDER, Lara S.; LAWHORN, Brian Griffin; MANNS, Sharada; PHILP, Joanne; WASHBURN, David G.; YE, Guosen; WO2015/104684; (2015); A1;,
Ether – Wikipedia,
Ether | (C2H5)2O – PubChem

Adding some certain compound to certain chemical reactions, such as: 20469-65-2, name is 1-Bromo-3,5-dimethoxybenzene, 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 20469-65-2. 20469-65-2

As follows are specific steps of: adding 3,5-dimethoxy-bromobenzene (1.74 g, 8.0 mmol, 1.0 equivalent (hereinafter referred to as ?eq?)) and a catalyst PdCl(PPh)(281 mg, 0.4 mmol, 0.05 eq) into a 100 mL Schlenk reaction flask; performing a cycle of vacuumizing and filling nitrogen gas in the flask for three times; adding dried and redistilled 1,2-dichloroethane (20 ml), triethylamine (7 ml, 40 mmol, 5.0 eq) and pinacol borane (HBpin) (3.5 ml, 24.0 mmol, 3.0 eq) into the reaction flask by a syringe; heating the reaction system to 90 C. and performing a reflux reaction for 4 hours; cooling the reaction system down to room temperature, then pouring the reaction solution into 20 ml water to terminate the reaction; extracting aqueous phases with ethyl acetate for several times and combining organic phases; washing the organic phases with a saturated saline solution and water for one time, respectively; drying with anhydrous magnesium sulfate and spin-drying the solvent; recrystallizing an obtained product in n-hexane/ethyl acetate to obtain a 1.8 g white solid with the yield of 85%. H NMR (400 MHz, CDCl) delta (ppm) 7.03 (s, 2H, benzene), 6.90 (s, 1H, benzene), 3.84 (s, 6H, -OCH3), 1.33 (s, 12H, -CH3).

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 1-Bromo-3,5-dimethoxybenzene.

Reference:
Patent; TECHNICAL INSTITUTE OF PHYSICS AND CHEMISTRY OF THE CHINESE ACADEMY OF SCIENCES; Li, Yi; Hao, Qingshan; Chen, Jinping; Zeng, Yi; Yu, Tianjun; US2015/353468; (2015); A1;,
Ether – Wikipedia,
Ether | (C2H5)2O – PubChem

20469-65-2, 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 20469-65-2 as follows.

1-iodo-3,5-dimethoxybenzene:A dried round bottom flaks was charged with 1-bromo-3,5-dimethoxy- benzene (15.0 g, 69.1 mmol) and dry tetrahydrofuran (275 cm3). The resulting solution was cooled down to -78 0C, then n-butyllithium (2.5 M in hexanes, 29.0 cm3, 72.6 mmol) was added dropwise over 10 minutes. The mixture was stirred at -78 0C for 1 hour, then 1,2-iodoethane (20.5 g, 72.6 mmol) in dry tetrahydrofuran (75 cm3) was added rapidly to the solution. After an additional 1 hour at -78 0C, the resulting mixture was warmed to room temperature and stirred overnight. The mixture was poured into saturated sodium thiosulfate solution (200 cm3), extracted with diethyl ether four times and dried over magnesium sulfate. The solvent was removed under reduced pressure, and the residue was recrystallized from methanol to obtain the title product as a white crystalline solid(13.0 g, yield 71 %). NMR (1H, 300 MHz1 CDCI3) : delta 6.85 (d, J = 2.3 Hz, 2H); 6.40 (t, J = 2.3 Hz, 1 H); 3.76 (s, 6H).

According to the analysis of related databases, 1-Bromo-3,5-dimethoxybenzene, the application of this compound in the production field has become more and more popular.

Reference:
Patent; MERCK PATENT GMBH; BLOUIN, Nicolas; MITCHELL, William; WANG, Changsheng; TIERNEY, Steven; WO2011/18144; (2011); A2;,
Ether – Wikipedia,
Ether | (C2H5)2O – PubChem