Category: 37895-73-1

Electric Literature of 37895-73-1,Some common heterocyclic compound, 37895-73-1, name is 1,2-Dibromo-4,5-dimethoxybenzene, molecular formula is C8H8Br2O2, 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: To a Schlenk tube (20 mL) were added PdCl2(MeCN)2 (26 mg, 0.10 mmol) and 2-dicyclohexylphosphino-2′,6′-dimethoxybiphenyl (SPhos, 0.16 g, 0.40 mmol). The Schlenk tube was capped with a rubber septum and then evacuated and purged with argon. The evacuation-purge operation was repeated twice. To the tube was added 1,4-dioxane (6.0 mL), 1,2-dibromobenzene (1.63 g, 0.82 mL, 5.0 mmol), NEt3 (3.04 g, 4.18 mL, 30.0 mmol), and pinacolborane (2.18 mL, 1.92 g, 15.0 mmol) in this order with syringes, respectively, through the septum. The reaction mixture was heated at 110 C and the progress of the reaction was monitored by gas chromatography. After the complete consumption of the dibromide was confirmed, the reaction mixture was then allowed to cool to room temperature. The resulting solution was filtered through a thin pad of Celite with EtOAc as the eluent. The organic solvent was removed under reduced pressure to give the crude product, which was purified by column chromatography on silica gel followed by recrystallization from hexane at -20 C, giving rise to 1,2-bis(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzene (3h, 0.83 g, 51%) as a colorless solid.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 1,2-Dibromo-4,5-dimethoxybenzene, its application will become more common.

Reference:
Article; Shimizu, Masaki; Nagao, Ikuhiro; Tomioka, Yosuke; Kadowaki, Tsugumi; Hiyama, Tamejiro; Tetrahedron; vol. 67; 41; (2011); p. 8014 – 8026;,
Ether – Wikipedia,
Ether | (C2H5)2O – PubChem

Synthetic Route of 37895-73-1, 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. 37895-73-1, name is 1,2-Dibromo-4,5-dimethoxybenzene, This compound has unique chemical properties. The synthetic route is as follows.

General procedure: A 12 mL vial was charged with [Pd(cinnamyl)Cl]2(1,5 mol%), dppp (3 mol%). and a stirring bar. Then, 1,2-dibromo-benzene(0.5 mmol), DBU (4.0 eq) and toluene (3 mL) were injected by syringe underargon. The vial (or several vials) was placed in an alloy plate, which wastransferred into a 300 mL autoclave of the 4560 series from Parr Instrumentsunder argon atmosphere. After flushing the autoclave three times with CO, apressure of 10 bar of CO was adjusted at ambient temperature. Then, thereaction was performed for 16-24 h at 140 oC. After the reactioncompleted, the autoclave was cooled down with ice water to room temperature andthe pressure was released carefully. After evaporation of the organic solventthe residue was adsorbed on silica gel and the crude product was purified bycolumn chromatography using EA/pentane(1:1) for phthalimides and MeOH/EA (1:40) for the amides as eluent.

The chemical industry reduces the impact on the environment during synthesis 1,2-Dibromo-4,5-dimethoxybenzene. I believe this compound will play a more active role in future production and life.

Reference:
Article; Chen, Jianbin; Natte, Kishore; Wu, Xiao-Feng; Tetrahedron Letters; vol. 56; 2; (2015); p. 342 – 345;,
Ether – Wikipedia,
Ether | (C2H5)2O – PubChem

Electric Literature of 37895-73-1, These common heterocyclic compound, 37895-73-1, name is 1,2-Dibromo-4,5-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.

General procedure: A Schlenk flask was charged under argon with 1 equiv of dihaloarene, 0.2 equiv of CuI, 0.22 equiv of Cy3PHBF4, and 0.1 equiv of PdCl2(PPh3)2. The flask was closed, evacuated, and filled with argon (the procedure was repeated thrice), 8 mL of DMF (per millimole of dihaloarene), 4 equiv of triethylamine, and 3 equiv of lactone 1a or 1b were added with a syringe, and the mixture was heated for 8 h at 100C. The mixture was cooled and concentrated under reduced pressure, and the products were isolated by column chromatography using heptane-ethyl acetateas eluent.

The synthetic route of 37895-73-1 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Ghochikyan; Samvelyan; Galstyan; Gevorgyan; Vardanyan; Grigoryan; Langer; Russian Journal of Organic Chemistry; vol. 53; 12; (2017); p. 1833 – 1839; Zh. Org. Khim.; vol. 53; 12; (2017); p. 1797 – 1803,7;,
Ether – Wikipedia,
Ether | (C2H5)2O – PubChem

37895-73-1, name is 1,2-Dibromo-4,5-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. HPLC of Formula: C8H8Br2O2

A flask containing 4,5-dibromoveratrole (500 mg, 1.69 mmol), 4-fluorophenylboronic acid (946 mg, 6.76 mmol), Pd(OAc)2 (38 mg, 0.169 mmol), XPhos (161 mg, 0.338 mmol), and K2CO3 (1.4 g, 10.1 mmol) was degassed and dioxane (10 mL) and H2O (5 mL) were added. Reaction was refluxed at 102 C. overnight then cooled to RT and diluted with EtOAc. Solution was washed with saturated NaHCO3 solution followed by brine and organic layer was collected, dried over Na2SO4, and concentrated. Chromatography using ISCO max gradient 10% EtOAc/hexane yielded product as a white solid (525 mg, 95% yield); 1H NMR (400 MHz) (CDCl3) delta 7.12-7.08 (m, 4H), 6.96-6.91 (m. 6H), 3.97 (s, 6H); 13C NMR (100 MHz) (CDCl3) delta 161.6 (JC,F=244 Hz), 148.4, 137.3 (JC,F=3 Hz), 132.1, 131.4 (JC,F=8 Hz), 114.9 (JC,F=21 Hz), 113.6.

The synthetic route of 37895-73-1 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; RUTGERS, THE STATE UNIVERSITY OF NEW JERSEY; LaVoie, Edmond J.; Arnold, Eddy; Bauman, Joseph D.; Kerrigan, John E.; Parhi, Ajit K.; Das, Kalyan; Kelley, Cody; Patel, Dishaben V.; US2015/322022; (2015); 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. 37895-73-1, name is 1,2-Dibromo-4,5-dimethoxybenzene, A new synthetic method of this compound is introduced below., Application In Synthesis of 1,2-Dibromo-4,5-dimethoxybenzene

a) Preparation of 4′,5′-Dimethoxy-[1,1′:2′,1″-terphenyl]-4,4″-dicarbonitrile A flask containing 4,5-dibromoveratrole (407 mg, 1.375 mmol), 4-cyanophenylboronic acid (606 mg, 4.125 mmol), Pd(PPh3)4 (159 mg, 0.1375 mmol), and Na2CO3 (729 mg, 6.875 mmol) was degassed and dioxane (6 mL) and H2O (3 mL) were added. Reaction was refluxed at 102 C. overnight then cooled to RT and diluted with EtOAc. Solution was washed with saturated NaHCO3 solution followed by brine and organic layer was collected, dried over Na2SO4, and concentrated. Chromatography using ISCO max gradient 50% EtOAc/hexane yielded product as a light yellow solid (467 mg, quantitative); 1H NMR (400 MHz) (CDCl3) delta 7.46-7.44 (m, 4H), 7.14-7.12 (m, 4H), 6.83 (s, 2H), 3.89 (s, 6H); 13C NMR (100 MHz) (CDCl3) delta 149.4, 145.6, 132.0, 131.3, 130.6, 118.7, 113.5, 110.6, 56.2.

The synthetic route of 37895-73-1 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; RUTGERS, THE STATE UNIVERSITY OF NEW JERSEY; LaVoie, Edmond J.; Arnold, Eddy; Bauman, Joseph D.; Kerrigan, John E.; Parhi, Ajit K.; Das, Kalyan; Kelley, Cody; Patel, Dishaben V.; US2015/322022; (2015); A1;,
Ether – Wikipedia,
Ether | (C2H5)2O – PubChem

Adding a certain compound to certain chemical reactions, such as: 37895-73-1, name is 1,2-Dibromo-4,5-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 37895-73-1, Formula: C8H8Br2O2

A 10 mL of a 1.6 M n-BuLi solution and 50 mL ofabsolute tetrahydrofuran were charged into a Schlenk flask (250 mL), the flask was cooled down to -20C,and a solution of 4.7 g (15.9 mmol) of 1,2-dibromo-5,6-dimethoxybenzene in 30 mL of absolute tetrahydrofuranwas added within half an hour ensuring thatthe temperature of the mixture did not exceed -20C.After stirring, a preliminarily prepared solution of3.53 g (16 mmol) of chlorodiphenylphosphine in20 mL of absolute tetrahydrofuran was added dropwisewithin an hour. Then the cooling was removed,and it was allowed to warm up to room temperature. A sample for GC-MS was collected (having preliminarytreated the mixture by a solution of sodium bicarbonate).The analysis showed the presence of 81% targetproduct of the total weight of the dry organic residuein the mixture. The solution was evaporated to dryness,and methanol was added to the residue. A viscousyellow precipitate was formed. The solvent wasevaporated, and diethyl ether was added. A fine whiteprecipitate was formed. The formed precipitate wasground, filtered off, and dried. Yield 3.82 g (60%). 1H NMR spectrum (300 MHz,CD2Cl2): delta (ppm) 7.42 (t, J = 3.5 Hz, 8H, Ar-H),7.08-7.03 (m, 12H, Ar-H), 6.82 (s, 2H, Ar-H), 3.18(s, 6H, OCH3). 31P{1H} spectrum (121.49 MHz,CDCl3): delta (ppm) -12.73 (s, PPh2).

At the same time, in my other blogs, there are other synthetic methods of this type of compound, 1,2-Dibromo-4,5-dimethoxybenzene, and friends who are interested can also refer to it.

Reference:
Article; Cheredilin; Sheloumov; Senin; Kozlova; Afanas?ev; Bespalova; Petroleum Chemistry; vol. 59; (2019); p. S72 – S87; Neftekhimiya;,
Ether – Wikipedia,
Ether | (C2H5)2O – PubChem

Adding a certain compound to certain chemical reactions, such as: 37895-73-1, name is 1,2-Dibromo-4,5-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 37895-73-1, Formula: C8H8Br2O2

A dried round-bottom flask was charged with the correspondingdibromoaryl (16.89 mmol, 1 eq) and furan (84.47 mmol, 5 eq) in dry toluene (50 mL) under argonatmosphere. The solution was cooled at -78 C and n-BuLi 1.6M in THF (18.58 mmol, 1.1 eq) was addeddropwise. After complete addition, the solution was warmed up to -40 C, extracted with EtOAc (3x20mL), dried over magnesium sulfate and concentrated under vacuum. The residue was purified bychormatography column (EtOAc/heptane). From 4,5-dibromoveratrol (5 g), 1.91 g of 1,4-dihydro-6,7-dimethoxy-1,4-epoxynaphthalene (56% yield) were obtained as a white solid (“H-NMR (500 MHz,CDCl3): (ppm) 7.01 (s, 21H), 6.94 (s, 21H), 5.65 (s, 21H), 3.82 (s, 6H)). From 5,6-dibromo-1,3-benzodioxole (4.73 g) were obtained 3.17 g of 5,8-dihydro-5,8-epoxynaphtho[2,3-d][1,3]dioxole (81%yield) as a white solid (“H-NMR (300 MHz, CDCl3): (ppm) 7.07 (s, 2H), 6.86 (s, 2H), 5.96 (d, 1H, J =1.4 Hz), 5.91 (d, 1H, J = 1.4 Hz), 5.66 (s, 2H)).

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, 1,2-Dibromo-4,5-dimethoxybenzene, other downstream synthetic routes, hurry up and to see.

Reference:
Article; Deyris, Pierre-Alexandre; Caneque-Cobo, Tatiana; Gomes, Filipe; Narbonne, Vanessa; Maestri, Giovanni; Malacria, Max; Heterocycles; vol. 88; 1; (2014); p. 807 – 815;,
Ether – Wikipedia,
Ether | (C2H5)2O – PubChem

Synthetic Route of 37895-73-1,Some common heterocyclic compound, 37895-73-1, name is 1,2-Dibromo-4,5-dimethoxybenzene, molecular formula is C8H8Br2O2, 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: To a Schlenk tube (20 mL) were added PdCl2(MeCN)2 (26 mg, 0.10 mmol) and 2-dicyclohexylphosphino-2′,6′-dimethoxybiphenyl (SPhos, 0.16 g, 0.40 mmol). The Schlenk tube was capped with a rubber septum and then evacuated and purged with argon. The evacuation-purge operation was repeated twice. To the tube was added 1,4-dioxane (6.0 mL), 1,2-dibromobenzene (1.63 g, 0.82 mL, 5.0 mmol), NEt3 (3.04 g, 4.18 mL, 30.0 mmol), and pinacolborane (2.18 mL, 1.92 g, 15.0 mmol) in this order with syringes, respectively, through the septum. The reaction mixture was heated at 110 C and the progress of the reaction was monitored by gas chromatography. After the complete consumption of the dibromide was confirmed, the reaction mixture was then allowed to cool to room temperature. The resulting solution was filtered through a thin pad of Celite with EtOAc as the eluent. The organic solvent was removed under reduced pressure to give the crude product, which was purified by column chromatography on silica gel followed by recrystallization from hexane at -20 C, giving rise to 1,2-bis(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzene (3h, 0.83 g, 51%) as a colorless solid.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 1,2-Dibromo-4,5-dimethoxybenzene, its application will become more common.

Reference:
Article; Shimizu, Masaki; Nagao, Ikuhiro; Tomioka, Yosuke; Kadowaki, Tsugumi; Hiyama, Tamejiro; Tetrahedron; vol. 67; 41; (2011); p. 8014 – 8026;,
Ether – Wikipedia,
Ether | (C2H5)2O – PubChem

Synthetic Route of 37895-73-1,Some common heterocyclic compound, 37895-73-1, name is 1,2-Dibromo-4,5-dimethoxybenzene, molecular formula is C8H8Br2O2, 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: A solution of 6.00 g (22.8 mmol) of 1,2-dibromo-4,5-dimethylbenzene in 12 mL of tetrahydrofuran wasadded to preliminary prepared 30 mL of a 1M solutionof iso-PrMgLiCl in tetrahydrofuran and stirred at -17to -13C. After 3 h, 5.12 g (23.25 mmol) of chlorodiphenylphosphinewas added dropwise to the solutionat -20 to -10C. The obtained solution was stirred for30 min at -10C, and then it was allowed to warm upto room temperature, stirred for additional 16 h, andevaporated. 30 mL of methylene chloride and 20 mLof a saturated aqueous solution of ammonium chloridewere added to the residue. The organic phase wasseparated and dried over anhydrous sodium sulfate.The residue after the evaporation was recrystallizedusing an ethanol-acetone mixture.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 1,2-Dibromo-4,5-dimethoxybenzene, its application will become more common.

Reference:
Article; Cheredilin; Sheloumov; Senin; Kozlova; Afanas?ev; Bespalova; Petroleum Chemistry; vol. 59; (2019); p. S72 – S87; Neftekhimiya;,
Ether – Wikipedia,
Ether | (C2H5)2O – PubChem