Category: 20469-65-2

20469-65-2, name is 1-Bromo-3,5-dimethoxybenzene, 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. SDS of cas: 20469-65-2

To a mixture of 1-bromo-3,5-dimethoxybenzene (15 g, 69.1 mmol) in dichloromethane (500 ml) at 0 C. was added BBr3 (14.37 ml, 152 mmol) dropwise over 5 minutes at 0 C. The reaction mixture was allowed to warm to room temperature and stirred for 5 hours. The reaction was then cooled to 0 C. 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 C. 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 through a through 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 (m/z) 189.0 (M+).

The synthetic route of 20469-65-2 has been constantly updated, and we look forward to future research findings.

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; LAWHORN, Brian Griffin; MANNS, Sharada; PHILP, Joanne; WASHBURN, David G.; YE, Guosen; (190 pag.)US2016/340328; (2016); A1;,
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Synthetic Route of 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.

In a clean dry round bottom flask, l-bromo-3.5-dimethoxybenzene (8.00 g, 36.9 mmol) was added to 300 ml of dry dichloromethane. The solution was cooled down to 0C and BetaIota (25.00 g, 100 mmol) was added dropwise. After 2 hours, the mixture was allowed to warm to room temperature and stirred over night. Methanol (10 ml) was added dropwise to terminate the reaction. The mixture was poured into water and stirred for 2 hours. Then saturated sodium bicarbonate (100 ml) was added and extracted with ethyl acetate. The organic layer was washed with saturated sodium bicarbonate, brine and then dried over Na2S04. The residue, after concentration, was purified using chromatography using ethyl acetate/hexane (1:4 v/v) eluent. Yield = 4.39 g (63%).

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-3,5-dimethoxybenzene, its application will become more common.

Reference:
Patent; POLYMEDIX, INC.; UNIVERSITY OF MASSACHUSETTS; LI, Yan; THAKER, Hitesh; TEW, Gregory N.; LIU, Dahui; PAN, Wenxi; WO2013/90185; (2013); A1;,
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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. 20469-65-2, name is 1-Bromo-3,5-dimethoxybenzene, A new synthetic method of this compound is introduced below., Formula: C8H9BrO2

Example 28 Synthesis of 1-Bromo-3,5-dihydroxybenzene (33) [0118] 1-bromo-3,5-dimethoxybenzene (32) (1.00 g, 4.60 mmol) was dissolved in dry dichloromethane (40 ml) and cooled in an ice bath. Boron tribromide (1.33 ml, 13.82 mmol) was added and the mixture was stirred on 2 h. The mixture was allowed to warm up to room temperature and stirred overnight. Methanol (1.4 ml) was added drop-wise to terminate the reaction, and the mixture was poured into water (50 ml) and stirred at RT for 2 h. Reaction mixture was neutralized with NaHCO3 and the mixture extracted twice with ethyl acetate (30 ml). Combined organic layers were dried over Na2SO4 and evaporated to dryness. Product was purified by column chromatography using silica gel as stationary phase and methanol:dichloromethane (5:95) as eluent. Product was a white solid. Yield: 0.71 g (81%). 1HNMR (DMSO-d6, delta ppm): 9.68 (2H, s), 6.38 (2H, d, J=2 Hz), 6.19 (1H, dd, J=2 Hz).

The synthetic route of 20469-65-2 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; DHR Finland OY; Meltola, Niko; Takalo, Harri; Sund, Henri; US2013/183771; (2013); A1;,
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Application of 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.

The Pd-catalyzed cross-coupling reaction of 5-Bromo-l,3-dimethoxybenzene with allyl boronic acid pinacol ester produced 5-allyl~l,3-dimethoxybenzene 1 in excellent yield; Example 20 Synthesis of 5-AUyl-l,3-dimethoxybenzene5-Bromo-l,3-dimethoxybenzene (2.13 g, 9.8 mralphaol), CsF (2.88 g, 19.0 mmol), and Pd(Ph3)4 (0.57-1.13 g, 0.5-1.0 mmol) were weighed into a flame-dried Schlenk flask and put under a flow of argon. THF (80 mL) was added to the flask via syringe, and the resulting suspension was stirred for 30 min at room temperature. AHyI boronic acid pinacol ester (2.96 g, 17.6 mmol) in THF (40 ml) was added and the resulting mixture was heated to reflux for 30 h. Another portion of CsF (2.88 g, 19.0 mmol) and Pd(Ph3)4 (0.57-1.13 g, 0.5-1.0 mmol) were added and the reaction was continued to reflux for 24 h. The reaction mixture was diluted with petroleum ether (100 ml) followed by H2O (100 ml). The layers were separated and the aqueous layer was extracted with petroleum ether (2 x 80 ml). The combined organic layers were washed with H2O (100 ml), and brine (100 ml). The solution was dried over MgSO4 and evaporated to dryness. The crude product was purified by column chromatography (silica, eluent: hexanes/benzene = 3:2) to give 1.60 g (92%) of 5-Allyl-l,3- dimethoxybenzene. 1H NMR (CDCl3): delta 3.33 (d, J = 6.7 Hz, 2H, CH2CH=CH2), 3.77 (s, 6H, OCHi), 5.02-5.11 (m, 2H5. CH2CH=CH2), 5.89-5.99 (m, 1Eta, CH2CH=CH2), 6.33-6.38 (m, 3H).

The synthetic route of 20469-65-2 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; THE UNIVERSITY OF NORTH CAROLINA AT CHAPEL HILL; RUTERGS UNIVERSITY; WO2007/8847; (2007); A2;,
Ether – Wikipedia,
Ether | (C2H5)2O – PubChem

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. 20469-65-2, name is 1-Bromo-3,5-dimethoxybenzene, A new synthetic method of this compound is introduced below., COA of Formula: C8H9BrO2

Example 26; Compound No.7; (S)-2-amino-N-(5-(3-methoxy-5-(piperidin-4-yloxy)phenyl)pent-4-ynyl)pent-4-ynamide; STEP A: 3-Bromo-5-methoxyphenol; 1-Bromo-3,5-dimethoxy-benzene (0.217 g, 0.001 mol) and KCN (0.20 g, 0.003 mol) were taken up into DMSO (10 mL) and the resulting mixture stirred at 120 C. for six hours, then at 150 C. overnight. The mixture was maintained at this temperature, with stirring for another day. The reaction was then quenched with water and the resulting mixture extracted with EtOAc. The organic layer was washed with saturated NaHCO3, brine, then dried over sodium sulfate and the solvent removed in vacuo. The resulting residue was purified on normal phase chromatography (Heptane/EtOAc) to yield 3-bromo-5-methoxyphenol. MH+ 203, 205

The synthetic route of 20469-65-2 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Parker, Michael H.; Hlasta, Dennis J.; Huang, Yifang; Reitz, Allen B.; Lawson, Edward C.; Schubert, Carsten; Strobel, Eric; Tounge, Brett A.; White, Kimberly; Winters, Michael P.; Ghosh, Shyamali; US2011/105562; (2011); A1;,
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Electric Literature of 20469-65-2, In the next few decades, the world population will flourish. As the population grows rapidly and people all over the world use more and more resources, all industries must consider their environmental impact. 20469-65-2, name is 1-Bromo-3,5-dimethoxybenzene belongs to ethers-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below.

A. To a solution of 1-bromo-3,5-dimethoxybenzene (3.01 g, 13.9 mmol) in dry THF (25 mL) at -78C under argon was added a solution of n-BuLi (2.2 M in hexanes, 7.00 mL, 15.4 mmol) dropwise and the mixture stirred for 40 mm. A solution of iodine in dry THF (20 mL) was then added dropwise and the reaction allowed to stir for an additional 45 mm at -78C before quenching with 20% aqueous Na25203 (45 mL) and warming to room temperature. The mixture was diluted with EtOAc (50 mL), the layers separated and the organic layer washed with brine (50 mL), dried (Mg504) and concentrated to a yellow solid (3.12 g). Purification of the crude product by chromatography on silica gel (20% EtOAc/hexanes) gave 1-iodo-3,5- dimethoxybenzene (Compound No. 31, 2.01 g, 55%) as a white solid.

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-3,5-dimethoxybenzene, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; AQUINOX PHARMACEUTICALS INC.; MACKENZIE, Lyoyd, F.; MACRURY, Thomas, B.; HARWIG, Curtis; BOGUCKI, David; RAYMOND, Jeffery, R.; PETTIGREW, Jeremy, D.; KHLEBNIKOV, Vladimir; SHAN, Rudong; WO2014/110036; (2014); A1;,
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Application of 20469-65-2, These common heterocyclic compound, 20469-65-2, name is 1-Bromo-3,5-dimethoxybenzene, 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.

To a dichloromethane solution (300 mL) of 1-bromo-3.5-dimethoxaybenzene (8.00 g, 36.9 mmol) in ice bath was added BBr3 (25.00 g, 100 mmol) dropwise. After 2 hours, themixture was allowed to warm to room temperature and stirred over night. Methanol (10 mL) was added dropwise to terminate the reaction. The mixture was poured into water and stirred for 2 hours, then saturated sodium bicarbonate (100 mL) was added and extracted with dichloromethane. The organic layer was washed with saturated sodium bicarbonate, brine, and then dried over Na2SO4 The residue, after concentration, was purified using chromatography(eluent: methoh/DCM: 2/98, v/v). A white solid (1.0 g) was obtained as product. LC-MS and HNMR are nice.

The synthetic route of 20469-65-2 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; CELLCEUTIX CORPORATION; FAN, Xiaodong; XU, Yongjiang; LIU, Dahui; COSTANZO, Michael J.; WO2014/93225; (2014); A2;,
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Related Products of 20469-65-2, These common heterocyclic compound, 20469-65-2, name is 1-Bromo-3,5-dimethoxybenzene, 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.

Example 19 Synthesis of (1R,10R,11S,16S)-3,5-dimethoxy-1,11,15,15-tetramethyl-8-oxatetracyclo[8.8.0.02,7.011,16]octadeca-2,4,6-triene To a stirred solution of 1-bromo-3,5-dimethoxybenzene (35) (2.17 g, 10.0 mmol) in THF (50 mL), cooled to -78 C., and n-BuLi (12.5 mL, 1.6 M in hexane, 20.0 mmol) was added dropwise. The mixture was allowed to warm to -20 C. over 2.5 h. The reaction was diluted with EtOAc (300 mL) and washed with water (150 mL). The organic layer was separated, dried (Na2SO4) and concentrated. Purification by column chromatography on silica gel (Hexanes/EtOAc, 2:1) gave 1-iodo-3,5-dimethoxybenzene (36) (1.6 g, 60%) as a brown oil.

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; Aquinox Pharmaceuticals Inc.; US2011/136802; (2011); A1;,
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Reference of 20469-65-2, 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. 20469-65-2, name is 1-Bromo-3,5-dimethoxybenzene, This compound has unique chemical properties. The synthetic route is as follows.

Under a nitrogen atmosphere,2.92 g, 13.82 mmol of 1-bromo-3,5-dimethoxybenzene was dissolved in 80 ml of dry DMF,Continuous addition of 3.86g,15.20 mmol of pinacol diboron,2.10 g, 20.73 mmol KOAc,1.56 g, 1.91 mmol PdCl2 (dppf) · CH2Cl2,The mixture was stirred at 80 C for 39 hours,The resulting solution was distilled under reduced pressure to remove DMF,CH2Cl2 extraction of organic phase,Na2SO4 dehydration,After distillation under reduced pressure by column chromatography.The stationary phase was a spherical silica gel of 63 to 210 m,The EtOAc / CH3 (CH2) 4CH3 solution with a fixed phase diameter of 7.5 cm in height of 8 cm and a mobile phase of 40/60,The purified white material was purified by column chromatography with 2.18 g of 5.22 mmol of 4-bromo-2,6-bis [2- (1-methyl) benzimidazolyl] pyridine in 60 ml of anhydrous DMF,2.79 g, 28.46 mmol KOAc,0.87 g, 1.06 mmol PdCl2 (dppf) · CH2Cl2,The mixture was stirred at 80 C for 60 hours,The resulting solution was distilled under reduced pressure to remove DMF,CH2Cl2 extraction of organic phase,Dehydration of Na2SO4, distillation under reduced pressure by column chromatography,The stationary phase was a spherical silica gel of 63 to 210 m,Fixed phase diameter of 7.5cm height of 8cm,The mobile phase consisted of 60/40 EtOAc / CH3 (CH2) 4CH3 solution,The white intermediate 1 purified by column chromatography was dissolved in 50 ml of anhydrous CH2Cl2,In the ice bath slowly drip 1.0M, 15ml, 15mmol of BBr3 (dropping time 30min)After completion of the dropwise addition, the temperature was gradually raised to room temperature for 12 hours,The resulting solution was quenched by the dropwise addition of 20 ml of water in an ice-water bath,The aqueous phase was adjusted to pH to neutral and the organic phase was extracted with EtOAc.After washing with water, Na2SO4 was dehydrated, distilled under reduced pressure and washed with Hex. After filtration, the white intermediate 2 was recrystallized from DMSO / H2O and dissolved with 1.50 g of 4.45 mmol of 1- (4-bromobutyl) -pyrene 60 ml of DMF solution,1.52 g, 11.05 mmol of K2CO3 was added and stirred at 80 C for 90 h. The organic phase was extracted by distillation under reduced pressure. The organic phase was extracted with CH2Cl2 and dehydrated with Na2SO4. After distillation under reduced pressure, the column was purified by column chromatography using a spherical silica gel of 63 to 210 m A mixed solution of 30/70 EtOAc / CH2Cl2 with a diameter of 7.5 cm and a mobile phase of 30 cm and a mobile phase was purified by column chromatography to give the product Py2G1MeBip as a white product.

The chemical industry reduces the impact on the environment during synthesis 1-Bromo-3,5-dimethoxybenzene. I believe this compound will play a more active role in future production and life.

Reference:
Patent; KUNMING UNIVERSITY OF SCIENCE AND TECHNOLOGY; WANG, HUA; YANG, LI; LI, KONGZHAI; WEI, YONGGANG; ZHU, XING; (27 pag.)CN104231007; (2017); B;,
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Related Products of 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.

Example 24 Synthesis of (1R,10R,11S,16S)-1,11,15,15-tetramethyl-3,5-bis(propan-2-yloxy)-8-oxatetracyclo[8.8.0.02,7.011,16]octadeca-2,4,6-triene To a solution of (35) (15.0 g, 69.0 mmol) in CH2Cl2 (40 mL), cooled to 0 C., a 1 M BBr3 solution in CH2Cl2 (140 mL, 140 mmol) was added dropwise. The ice bath was removed and the reaction was stirred at room temperature for 18 h. The reaction was quenched with MeOH and concentrated. The residue was dissolved in EtOAc (500 mL) and washed with water (300 mL). The organic layer was separated, dried (Na2SO4) and concentrated to give 5-bromobenzene-1,3-diol (45) (13.03 g, >99%) as an orange oil.

The synthetic route of 20469-65-2 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Aquinox Pharmaceuticals Inc.; US2011/136802; (2011); A1;,
Ether – Wikipedia,
Ether | (C2H5)2O – PubChem