Category: 74137-36-3

Synthetic Route of 74137-36-3, As we all know, there are many different methods for the synthesis of a compound, and people can choose the synthesis method that suits their own laboratory according to the actual situation. 74137-36-3 name is 1,3-Dibromo-5-methoxybenzene, This compound is widely used in many fields, so it is necessary to find a new synthetic route. The downstream synthesis method of this compound is introduced below.

A solution of 1,3-dibromo-5-methoxybenzene (24.5 g, 92.13 mmol, 1 equiv) in Et2O (400 mL) under nitrogen, cooled to -78 oC and stirred for 20 min was added n-BuLi (2.5mol/L in THF, 44 mL, 1.20 equiv) dropwised at -78 oC. The reaction mixture was continued to stir for 1h at -78 oC followed by addition of DMF (8.1 g, 110.55 mmol, 1.2 equiv) dropwise. After stirring for 45 min at -78oC, the reaction was quenched with water (200 ml) carefully and extracted with EtOAc (500 mL) twice. The combined organic layers were concentrated under reduced pressure to give a mixture, which was further triturated with hexane (200mL) to afford 3-bromo-5-methoxybenzaldehyde (45-2) (14.5 g, 73.2%) as a white solid.

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; CYTOKINETICS, INC.; CHUANG, Chihyuan; MORGAN, Bradley P.; VANDERWAL, Mark; WANG, Wenyue; ASHCRAFT, Luke W.; (362 pag.)WO2019/144041; (2019); A1;,
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. 74137-36-3, name is 1,3-Dibromo-5-methoxybenzene, A new synthetic method of this compound is introduced below., Recommanded Product: 1,3-Dibromo-5-methoxybenzene

step 2-To a solution of 57b (60 g, 0.2256 mol) and anhydrous Et2O (1 L) cooled to -78 C. and maintained under an Ar atmosphere was added dropwise over 30 min n-BuLi (100 mL, 0.2482 mol, 2.5M in hexane). The yellow solution was stirred at -78 C. for 20 min. To the reaction mixture was added dropwise dry DMF (19 mL, 248.2 mmol) over 15 min and the reaction stirred at -78 C. for 10 min before the cooling bath was removed and the reaction allowed to warm to -30 C. over 30 min. The reaction vessel was placed in an ice-water bath and warmed to -10 C. The mixture was slowly added to an ice cold saturated aqueous NH4Cl solution (400 mL). The organic layer was separated and the aqueous phase thrice extracted with Et2O. The combined extracts were washed with water, dried (MgSO4), filtered and evaporated to afford an oil which solidified on standing. The crude product was purified by SiO2 chromatography eluting with a hexane/EtOAc gradient (97:3 to 95:5) to afford 58.

The basis of chemical reaction formula synthesis, the synthesis route is composed of some specific reactions and combined according to certain logical thinking. We look forward to the emergence of more reaction modes in the future.

Reference:
Patent; Roche Palo Alto LLC; US2006/25462; (2006); A1;,
Ether – Wikipedia,
Ether | (C2H5)2O – PubChem

Electric Literature of 74137-36-3, A common heterocyclic compound, 74137-36-3, name is 1,3-Dibromo-5-methoxybenzene, molecular formula is C7H6Br2O, 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.

A 1.6 M solution of n-butyllithium in hexane (5.65 mL, 9.04 mmol) was dissolved in dry toluene (50 mL) under dry argon and cooled to -5¡ã C. Then a 2M solution of n-butylmagnesium chloride (2.26 mL, 4.52 mmol) was added slowly with the temperature held below 0¡ã C. over a period of 15 min. Stirring was continued for 45 min at -5¡ã C., followed by drop wise addition of a solution of 1,3-dibromo-5-methoxy-benzene (3.00 g, 11.3 mmol) in toluene (30 mL) with the temperature held below 0¡ã C. The mixture was stirred for 45 min at -5¡ã 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¡ã 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 of Na2S2O3 (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). 1-Bromo-3-iodo-5-methoxy-benzene (2.12 g, 60percent) was obtained as a yellow oil, which crystallized quickly upon standing.

The basis of chemical reaction formula synthesis, the synthesis route is composed of some specific reactions and combined according to certain logical thinking. We look forward to the emergence of more reaction modes in the future.

Reference:
Patent; Kelly, Martha; Lee, Younghee; Liu, Bin; Fujimoto, Ted; Freundlich, Joel; Dorsey, Bruce D.; Flynn, Gary A.; Husain, Arifa; US2006/270686; (2006); A1;,
Ether – Wikipedia,
Ether | (C2H5)2O – PubChem

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.

Succinic acid mono-{3-[4-chloro-3-(3,5-dicyano-phenoxy)-2-fluoro-benzyl]-4-methyl-5-oxo-4,5-dihydro-[1,2,4]triazol-1-ylmethyl} ester was prepared in a similar manner except steps 1 and 2 were omitted and 3,5-dibromophenol was used in the place of 3-bromo-5-chlorophenol in step 3 to afford I-4: mp 141.6-143.3¡ã C., MS (ES-): m/z 512, 1H NMR (d6-DMSO, 300 MHz) delta 12.2 (br.s, 1H), 8.23 (t, J=1.2 Hz, 1H), 7.95 (d, J=1.2 Hz, 2H), 7.52 (dd, J=1.5, 8.6 Hz, 1H), 7.35 (t, J=7.8 Hz, 1H), 7.34 (t, J=7.8 Hz, 1H), 5.63 (s, 2H), 4.09 (s, 2H), 3.14 (s, 3H) 2.52-2.43 (m, 4H). Anal. Calcd for C23H17FClN5O6: C, 53.76; H, 3.33; N, 13.63. Found: C, 53.68; H, 3.47; N, 13.35. 3,5-Dibromophenol was prepared from 3,5-dibromoanisole by demethylation with HBr/HOAc.

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 74137-36-3.

Reference:
Patent; Roche Palo Alto LLC; US2006/25462; (2006); A1;,
Ether – Wikipedia,
Ether | (C2H5)2O – PubChem

74137-36-3, As we all know, there are many different methods for the synthesis of a compound, and people can choose the synthesis method that suits their own laboratory according to the actual situation. 74137-36-3 name is 1,3-Dibromo-5-methoxybenzene, This compound is widely used in many fields, so it is necessary to find a new synthetic route. The downstream synthesis method of this compound is introduced below.

General procedure: 3-Bromo-5-methoxy-1 ,1 ‘-biphenyl was synthesised according to general procedures GP13 – from 1 ,3- dibromo-5-methoxybenzene (6.50 g, 24.4 mmol), phenylboronic acid (2.08 g, 17.0 mmol), Pd(PPh3)4 (1 .40 g, 5 molpercent), Na2C03 (6.47 g, 61 .0 mmol), toluene (70 ml_), ethanol (7.0 mL) and water (7.0 ml_); 100 ¡ãC, 16 h. Chromatographic purification (hexane) afforded a colourless oil (4.1 g, contained a small amount of impurity), which is used in the subsequent transformation as an impure mixture. H NMR of a pure chromatography fraction (400 MHz, DMSO-c/6) delta: 7.55-7.53 (m, 2H), 7.43-7.42 (m, 2H), 7.37 (d, J = 7.3 Hz, 1 H), 7.32-7.31 (m, 1 H), 7.03 (d, J = 1 .4 Hz, 2H), 3.85 (s, 3H). General procedures GP13 [00693] A mixture of bromide GP13_1 , Pd(PPh3)4, ArB(OR’)2, Na2C03, H20, EtOH and toluene was degassed with argon and then stirred at 100 ¡ãC for 16 h. After cooling to rt, the mixture was diluted with Et20 and filtered through celite. The organic solution was washed with H20, dried over Na2S04, filtered and the solvent was removed under reduced pressure. The crude was purified by chromatography to afford biaryl GP13_2.

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

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

To a solution of 1,3-dibromo-5-methoxy-benzene (60 g, 0.2256 mol) and anhydrous Et2O (1 L) cooled to -78 C. and maintained under an Ar atmosphere was added dropwise over 30 min n-BuLi (100 mL, 0.2482 mol, 2.5M in hexane). The yellow solution was stirred at -78 C. for 20 min. To the reaction mixture was added dropwise dry DMF (19 mL, 248.2 mmol) over 15 min and the reaction stirred at -78 C. for 10 min before the cooling bath was removed and the reaction allowed to warm to -30 C. over 30 min. The reaction vessel was placed in an ice-water bath and warmed to -10 C. The mixture was slowly added to an ice cold saturated aqueous NH4Cl solution (400 mL). The organic layer was separated and the aqueous phase thrice extracted with Et2O. The combined extracts were washed with water, dried (MgSO4), filtered and evaporated to afford an oil which solidified on standing. The crude product was purified by SiO2 chromatography eluding with a hexane/EtOAc gradient (3 to 5% EtOAc) to afford 3-bromo-5-methoxy-benzaldehyde.

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 1,3-Dibromo-5-methoxybenzene.

Reference:
Patent; Roche Palo Alto LLC; US2008/249151; (2008); 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¡ã 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

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.

Step 2: Preparation of 1-bromo-3-ethylsulfanyl-5-methoxy-benzene To a mixture 1,3-dibromo-5-methoxy-benzene (2.65 g, 10 mmol) and sodium thioethoxide (1.01 g, 12 mmol) was added dimethylformamide (30 mL) at room temperature. Then, the resulting light yellow solution was heated to 105¡ã C. and stirred for 2 h at which time TLC analysis of the mixture indicated the absence of starting material. The reaction mixture was cooled to room temperature and diluted with water (50 mL) and brine solution (50 mL). Then, the organic compound was extracted into ethyl acetate (3*50 mL). The combined extracts were washed with brine solution (150 mL) and dried over anhydrous magnesium sulfate. Filtration of the drying agent and the concentration of the solution under reduced pressure gave the crude residue which was purified by using an ISCO 120 g column chromatography, eluding with 0-20percent ethyl actetate in hexanes to obtain 1-bromo-3-ethylsulfanyl-5-methoxy-benzene (1.35 g, 55percent) as a white solid: EI(+)-HRMS m/e calcd for C9H11BrOS (M)+ 245.9715, found 245.9713.

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; Dominique, Romyr; Goodnow, JR., Robert Alan; Kowalczyk, Agnieszka; Lou, Jianping; Qiao, Qi; Siddurl, Achyutharao; Tilley, Jefferson Wright; US2009/227603; (2009); A1;,
Ether – Wikipedia,
Ether | (C2H5)2O – PubChem

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.

3,5-Dibromoanisole (15.57 g, 58.5 mmol) and tetrabutylammonium bromide (1.0 g, 3.1 mmol) were suspended in 48percent hydrobromic acid (100 mL) and refluxed for 3 days. After cooling to room temperature the reaction mixture was extracted with methylene chloride (3.x.60 mL). The combined organic layers were washed with water, dried over magnesium sulfate, and evaporated. The crude product was filtered over a pad of silica gel (ethyl acetate/heptane 10:1). After removal of the solvent, 14.23 g (97percent of 3,5-dibromophenol was obtained as pale brown needles.

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

Reference:
Patent; Kelly, Martha; Lee, Younghee; Liu, Bin; Fujimoto, Ted; Freundlich, Joel; Dorsey, Bruce D.; Flynn, Gary A.; Husain, Arifa; US2006/270686; (2006); A1;,
Ether – Wikipedia,
Ether | (C2H5)2O – PubChem