Category: 74137-36-3

Adding a certain compound to certain chemical reactions, such as: 74137-36-3, name is 1,3-Dibromo-5-methoxybenzene, 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 74137-36-3, Recommanded Product: 74137-36-3

To a solution of 1,3-dibromo-5-methoxybenzene (9.18 mmol, 1 eq) in 2 ml of xylene under a nitrogen atmosphere, acrylic acid (0.63 ml, 9.18 mmol, 1 eq), Pd(OAc)2 (1 mole percent, 20.66 mg), triphenylphosphine (4 mole percent, 69.2 mg) and triethylamine (19.278 ml, 2.7, 2.1 eq) are added. The reaction mixture is stirred at 100° C. for 11 h. Thereafter, 20 ml of water and 2 g of sodium carbonate were added, and the mixture was stirred at 100° C. for some minutes. The aqueous phase was subsequently separated and acidified. The precipitate that formed was dried and purified by means of column chromatography (eluent hexane/ethyl acetate 1/1) to obtain the desired product in a yield of 32percent (751 mg). C10H9Br3O; MW 256/258; 1H-NMR (CD3OD): delta 7.61 (d, J=16.1 Hz, 1H), 7.38-7.37 (m, 1H), 7.17-7.16 (m, 2H), 6.53 (d, J=16.1 Hz, 1H), 3.87 (s, 3H); 13C-NMR (CD3OD): delta 169.8, 162.3, 144.5, 138.9, 124.2, 121.4, 120.0, 113.4, 56.2

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, 1,3-Dibromo-5-methoxybenzene, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; Hartmann, Rolf; Frotscher, Martin; Oberwinkler, Sandrine; Ziegler, Erika; Messinger, Josef; Thole, Heinrich-Hubert; US2010/204234; (2010); A1;,
Ether – Wikipedia,
Ether | (C2H5)2O – PubChem

74137-36-3, The chemical industry reduces the impact on the environment during synthesis 74137-36-3, name is 1,3-Dibromo-5-methoxybenzene, I believe this compound will play a more active role in future production and life.

Tris(dibenzylideneacetone)dipalladium(0) (6.53 g, 7.15 mmol) was added in one portion to a stirred solution of the bromide of Preparation 1 (38.0 g, 143 mmol), 1,1′-bis(diphenylphosphino)ferrocene (9.3 g, 16.8 mmol) and zinc cyanide (20.0 g, 172 mmol) in N,N-dimethylformamide (300 ml) at room temperature under nitrogen. The reaction was heated at 100° C. for 14 hours and cooled to room temperature. Water (1500 ml) was added and the mixture was extracted with ethyl acetate (3.x.500 ml). The combined organics were filtered and the filtrate was washed with water (500 ml), dried over magnesium sulphate, filtered and concentrated under reduced pressure. The resulting solid was triturated with toluene (1000 ml) to provide the title compound (18.0 g) as a tan solid. 1H-NMR (300 MHz, CDCl3): delta=3.83 (3H, s), 7.31 (2H, s), 7.48 (1H, s).

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

Reference:
Patent; Pfizer Inc.; US2005/54707; (2005); A1;,
Ether – Wikipedia,
Ether | (C2H5)2O – PubChem

Adding a certain compound to certain chemical reactions, such as: 74137-36-3, name is 1,3-Dibromo-5-methoxybenzene, 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 74137-36-3, Quality Control of 1,3-Dibromo-5-methoxybenzene

General procedure: 2-Ethylhexyl 3-((3-bromo-5-methoxyphenyl)thio)propanoate was synthesised according to general procedures GP12 – from 1 ,3-dibromo-5-methoxybenzene (3.0 g, 1 1 .3 mmol), Pd2(dba)3 (0.25 mg, 2.5 mol%), Xantphos (0.32 mg, 5 mol%), 2-ethylhexyl-3-mercaptopropionate (1 .96 g, 9.02 mmol), DIPEA (4.15 ml_, 23.9 mmol) and toluene (30 ml_); 1 10 C, 8 h. Chromatography (12% EtOAc in hexane) afforded a pale orange solid (2.4 g, 66%). NMR (400 MHz, DMSO-c/6) delta 7.05 (t, J = 1 .6 Hz, 1 H), 6.99 (d, J = 2.0 Hz, 1 H), 6.87 (t, J = 2.0 Hz, 1 H), 3.95 (d, J = 5.6 Hz, 2H), 3.76 (s, 3H), 3.21 (t, J = 6.4 Hz, 2H), 2.63 (t, J = 6.8 Hz, 2H), 1 .52-1 .50 (m, 1 H), 1 .29-1 .24 (m, 8H), 0.87-0.82 (m, 6H). LCMS (ESI, -ve) m/z 217/219 (M-C11 H21O2)-. General procedures GP12 00690] Condition A – a mixture of bromide GP12_1 , Pd2(dba)3 (5 mol%), Xantphos (10 mol%), RSH (1 .0-1 .2 equiv.), NaO’Bu (1 .0-1 .2 equiv.) and ‘BuOH/toluene (1 :5) was degassed with argon and then stirred at 100 C for 16 h. After cooling to rt, the suspension was filtered through celite, washed with DCM and the solvent was removed under reduced pressure. Alternatively, the mixture was centrifuged at 2500 RPM for 5 minutes. The solution was decanted and concentrated under reduced pressure. The crude was purified by chromatography to afford sulfide GP12_2. (1128) [00691] Condition B – same as condition A, with DIPEA used instead of NaO’Bu and toluene used instead of ‘BuOH/toluene.

At the same time, in my other blogs, there are other synthetic methods of this type of compound, 1,3-Dibromo-5-methoxybenzene, and friends who are interested can also refer to it.

Reference:
Patent; THE INSTITUTE OF CANCER RESEARCH: ROYAL CANCER HOSPITAL; SPRINGER, Caroline; MARAIS, Richard; NICULESCU-DUVAZ, Dan; LEUNG, Leo; SMITHEN, Deborah; CALLENS, Cedric; TANG, Haoran; (403 pag.)WO2017/141049; (2017); A1;,
Ether – Wikipedia,
Ether | (C2H5)2O – PubChem

Application of 74137-36-3, These common heterocyclic compound, 74137-36-3, name is 1,3-Dibromo-5-methoxybenzene, 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 17 Synthesis of ethyl (E)-3-(3-bromo-5-methoxyphenyl)acrylate (17-1) Step One: To a solution of 3,5-dibromoanisole (1.01 g, 3.79 mmol) in acetonitrile (20 mL) at room temperature under nitrogen, palladium(II) acetate (42 mg, 0.19 mmol), tri(o-tolyl)phosphine (116 mg, 0.38 mmol), ethyl acrylate (0.36 mL, 3.38 mmol) and triethylamine (2.10 ml, 15.1 mmol) were added sequentially. The mixture was heated to reflux 4 hours, cooled to room temperature, diluted with ethyl acetate, and washed with water and brine. The organic layer was dried over magnesium sulfate, filtered and concentrated. The residue was purified by silica gel chromatography, eluting with 5percent ethyl acetate in hexanes. Fractions containing product were combined, concentrated and the residue was rechromatographed, eluting with 3percent increasing to 5percent ethyl acetate in hexanes to give ethyl (E)-3-(3-bromo-5-methoxyphenyl)acrylate (17-1, 354 mg) as a yellow oil.

The synthetic route of 74137-36-3 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Aviara Pharmaceuticals, Inc.; Biediger, Ronald J.; Benish, Michele A.; Hardy, Lindsay Bonner; Boyd, Vincent A.; Market, Robert V.; Thrash, Thomas P.; Young, Brandon M.; (83 pag.)US2018/312523; (2018); A1;,
Ether – Wikipedia,
Ether | (C2H5)2O – PubChem

Adding a certain compound to certain chemical reactions, such as: 74137-36-3, name is 1,3-Dibromo-5-methoxybenzene, 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 74137-36-3, Application In Synthesis of 1,3-Dibromo-5-methoxybenzene

2 mmol 3,5-dibromoanisole were dissolved in 10 ml THF and cooled to -78C. 2.4 mmol of n- BuLi were added dropwise and stirring was continued for 15 min. 3 mmol of methyl iodide were added and the mixture was allowed to slowly warm to ca. -200C over a period of ca. 2 h. IM HCl and dichloromethane were added and the phases were separated. 1.65 mmol of crude 3-bromo-5- methylanisole were taken to the next step without further purification.

If you are interested in these compounds, you can also browse my other articles.Thank you for taking the time to read this article. I hope you enjoyed it.

Reference:
Patent; KARO BIO AB; WO2008/43567; (2008); A1;,
Ether – Wikipedia,
Ether | (C2H5)2O – PubChem

Application of 74137-36-3, 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. 74137-36-3, name is 1,3-Dibromo-5-methoxybenzene belongs to ethers-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below.

A THF ( 150 mL) solution containing l ,3-dibromo-5-methoxybenzene (1.10 g, 4.10 mmol) and Pd(PPh3)4 (0.48 g, 0.41 mmol) was charged with a 0.5 M THF solution of 2-pyridylzinc bromide (21 mL, 10 mmol). The solution was stirred at reflux for 14 h, cooled and then quenched with a saturated aqueous NaHCO, solution ( 100 mL) and washed with aqueous EDTA. The crude product was extracted with diethyl ether (2 x 100 mL), and the organic fractions were collected and dried over MgS04. The solvent was removed in vacuo to afford an oil that was purified by column chromatography [AI2O3: Epsiloniota20, Rf = 0.60]; the resultant oily product converted to a white solid upon standing (850 mg; yield = 78percent). NMR (300 MHz, CDC13): delta = 8.70 (d, 2H, 3 J = 7 Hz, Ha), 8.20 (s, 1H, Hf, 7.77 (d, 2H, 3 J = 8 Hz, Hf, 7.75 (t, 2H, 3 J = 8 Hz, Hf), 7.66 (s, 2H, He), 7.25 (t, 2H, 3 J = 8 Hz, Hh), 3.97 (s, 3H, Hg); 13C NMR (100 MHz, CDCI3): delta = 160.7, 157.2, 149.7, 141.4, 136.9, 122.5, 121.0, 1 18.2, 1 13.3, 55.8; HRMS (EI): mlz, = 262.1 101 [(M)+] (calcd for Ci7Hi4N20+: mlz = 262.1 106).

The synthetic route of 1,3-Dibromo-5-methoxybenzene has been constantly updated, and we look forward to future research findings.

Reference:
Patent; BERLINGUETTE, Curtis P.; KOIVISTO, Bryan; ROBSON, Kiyoshi; WO2011/32269; (2011); A1;,
Ether – Wikipedia,
Ether | (C2H5)2O – PubChem

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. 74137-36-3, name is 1,3-Dibromo-5-methoxybenzene, This compound has unique chemical properties. The synthetic route is as follows., Quality Control of 1,3-Dibromo-5-methoxybenzene

Tris [(DIBENZYLIDENEACETONE)] [DIPALLADIUM (0)] (6.53g, 7. [15MMOL)] was added in one portion to a stirred solution of the bromide of Preparation 1 (38. [0G,] [143MMOL),] 1,1′-bis (diphenylphosphino) ferrocene (9.3g, 16. [8MMOL)] and zinc cyanide (20. [OG,] [172MOL)] in N,N-dimethylformamide (300ml) at room temperature under nitrogen. The reaction was heated at [100°C] for 14 hours and cooled to room temperature. Water (1500ml) was added and the mixture was extracted with ethyl acetate (3x500ml). The combined organics were filtered and the filtrate was washed with water (500ml). dried over magnesium sulphate, filtered and concentrated under reduced pressure. The resulting solid was triturated with toluene [(1000ML)] to provide the title compound [(18. 0G)] as a tan solid. [1H-NMR (300MHZ, CDCI3)] : 8 = 3.83 (3H, s), 7.31 (2H, s), 7.48 (1 H, s).

According to the analysis of related databases, 74137-36-3, the application of this compound in the production field has become more and more popular.

Reference:
Patent; PFIZER LIMITED; PFIZER INC.,; WO2004/29042; (2004); A1;,
Ether – Wikipedia,
Ether | (C2H5)2O – PubChem

74137-36-3, name is 1,3-Dibromo-5-methoxybenzene, 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. name: 1,3-Dibromo-5-methoxybenzene

General procedure: Typically, TDPP (200 mg, 0.27 mmol), dibromobenzene derivatives 0.11 mmol, anhydrous Cs2CO3(200 mg, 0.61 mmol), PivOH (7.9 mg, 0.08 mmol), Pd2(dba)3 (4.00 mg, 1.5 mol%), tris(o-methoxyphenyl)phosphine (3.08 mg, 3 mol%) were successively added into a Schlenk tube. The tube was purged by three repetitions of vacuum and argon filling. Then, 5 mL anhydrous toluene was added via syringe.The reaction solution was deoxygenated using three freeze-vacuum-thaw cycles, and then rigorouslystirred at 100 C for 24 h under argon atmosphere. Removal of the toluene by rotary evaporatoraorded the crude product, which was then purified by chromatogragh column (CC) on silica gelusing a mixture of CH2Cl2 and hexane as eluent, giving the target molecules Ms1~9.

The synthetic route of 74137-36-3 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Liu, Hui; Zhang, Xiao-Feng; Cheng, Jing-Zhao; Zhong, Ai-Guo; Wen, He-Rui; Liu, Shi-Yong; Molecules; vol. 24; 9; (2019);,
Ether – Wikipedia,
Ether | (C2H5)2O – PubChem

Reference of 74137-36-3, 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 74137-36-3 as follows.

[0353] A 1.6 M solution of n-butyllithium in hexane (5.65 niL, 9.04 mmol) was dissolved in dry toluene (50 mL) under dry argon and cooled to -5°C. Then a 2M solution of n-butylmagnesium chloride (2.26 mL , 4.52 mmol) was added slowly with the temperature held below 0°C over a period of 15 min. Stirring was continued for 45 min at -5°C, followed by drop wise addition of a solution of l,3-dibromo-5-methoxy-benzene (3.00 g, 11.3 mmol) in toluene (30 mL) with the temperature held below 00C. The mixture was stirred for 45 min at -5°C. A solution of iodine chloride (1.83 g, 11.3 mmol) in methylene chloride (20 mL) was added in the described manner and stirring continued for additional 20 min at -5°C. The mixture was warmed to room temperature. Water (50 mL) and toluene (50 mL) were added and the layers were separated. The organic layer was washed with a saturated aqueous solution OfNa2S2O3 (2 x 30 mL), water and brine (30 mL). The organic layer was dried (MgSO4) and concentrated to give the crude product which was purified by flash chromatography on silica gel (100 g, AcOEt/heptane 1:9). l-Bromo-3-iodo-5- methoxy-benzene (2.12 g, 60 percent) was obtained as a yellow oil, which crystallized quickly upon standing.

According to the analysis of related databases, 74137-36-3, the application of this compound in the production field has become more and more popular.

Reference:
Patent; LOCUS PHARMACEUTICALS, INC.; WO2008/8059; (2008); A1;,
Ether – Wikipedia,
Ether | (C2H5)2O – PubChem

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 74137-36-3 as follows. Application In Synthesis of 1,3-Dibromo-5-methoxybenzene

[3-(3-Bromo-5-cyano-phenoxy)-4-chloro-2-fluoro-phenyl]-acetic Acid Ethyl Ester (R-20c) step 1-n-BuLi (2.6 mL of a 1.6 M solution, 1.1 equiv) was added slowly to a solution of the R-21a (1.0 g, 3.8 mmol, CAS Reg. No. 74137-36-3) in Et2O (20 mL) cooled to -78 C. under an N2 atmosphere. The solution was stirred for 45 min, and DMF was added via syringe. The solution was warmed slowly to RT, added to saturated ammonium chloride, and extracted with ether. The organic phase was washed with brine and dried (MgSO4), filtered and evaporated to afford 0.80 g (98%) of R-21b.

According to the analysis of related databases, 74137-36-3, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Billedeau, Roland Joseph; Sweeney, Zachary Kevin; US2009/170856; (2009); A1;,
Ether – Wikipedia,
Ether | (C2H5)2O – PubChem