Category: 5279-32-3

Related Products of 5279-32-3, 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. 5279-32-3 name is 5,6-Dibromobenzo[d][1,3]dioxole, 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.

Method B: 4-Amino-1-(4-methoxybenzyl)-1H-imidazo[4,5-c]pyridine-2-thiol (100 mg, 0.349 mmol), 5,6-dibromo-1,3-benzodioxole (196 mg, 0.698 mmol), Pd2dba3 (16 mg, 1.8×10-2 mmol), Xantphos (21 mg, 3.5×10-2 mmol), and Cs2CO3 (227 mg, 0.698 mmol) were placed in a vial and degassed dioxane (1.2 mL) was added to the mixture. After heating at 100 C. for 10 h, the mixture was diluted with EA, washed with brine, dried (Na2SO4), filtered, and concentrated in vacuum. The residue was purified by column chromatography (SiO2, MeOH/CH2Cl2, 0 to 10%) to afford the title compound (54 mg, 31%).

At the same time, in my other blogs, there are other synthetic methods of this type of compound, 5,6-Dibromobenzo[d][1,3]dioxole, and friends who are interested can also refer to it.

Reference:
Patent; Myrexis, Inc.; US8017780; (2011); B1;,
Bromide – Wikipedia,
bromide – Wiktionary

Some common heterocyclic compound, 5279-32-3, name is 5,6-Dibromobenzo[d][1,3]dioxole, molecular formula is C7H4Br2O2, 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. COA of Formula: C7H4Br2O2

Under nitrogen atmosphere, 5,6-Dibromo-1,3-benzodioxole (13a, 1.58 g, 5.64 mmol), zinc(II)cyanide (670 mg, 5.71 mmol) and [1,1?-bis(diphenylphosphino)ferrocene]dichloropalladium(II) (208 mg, 284 mumol) were dissolved in anhydrous dimethylacetamide (12 mL) andstirred for 3 h at 150 C. Subsequently, the mixture was diluted with ethyl acetate (50 mL),washed with water (2 × 50 mL), the organic layer dried over magnesium sulfate and the solventremoved in vacuo. The crude product was purified by column chromatography using silica anddichloromethane as eluent (Rf = 0.50) to obtain a colourless solid (829 mg, 4.82 mmol, 85%).1H NMR (500MHz, CDCl3, 300 K): delta = 7.14 (s, 2H), 6.21 (s, 2H) ppm;13C NMR (125 MHz, CDCl3, 300 K): delta = 151.7 (2C), 115.5 (2C), 112.8 (2C), 111.0 (2C), 104.0 ppm;MS (EI, 70 eV): m/z (%) = 172 (100) [M]+;HR-MS (EI, 70 eV): m/z = calcd. for C9H4N2O2 [M]+ 172.0267, found 172.0273.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 5279-32-3, its application will become more common.

Reference:
Article; Hamer, Sebastian; Roehricht, Fynn; Jakoby, Marius; Howard, Ian A.; Zhang, Xianghui; Naether, Christian; Herges, Rainer; Beilstein Journal of Organic Chemistry; vol. 15; (2019); p. 1331 – 1338;,
Bromide – Wikipedia,
bromide – Wiktionary

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. 5279-32-3, name is 5,6-Dibromobenzo[d][1,3]dioxole, A new synthetic method of this compound is introduced below., Quality Control of 5,6-Dibromobenzo[d][1,3]dioxole

Preparation of 5-(6-bromobenzo[d][1,3]dioxol-5-yl)pyrazin-2-amine (15).; Palladium tetrakis-triphenylphosphine (31 mg, 30 mumol) was added to a degassed solution of dibromide 10 (150 mg, 54 mumol) and boronate 14 (130 mg, 59 mumol) in dioxane:acetonitrile:water (9:9:2, 2.7 mL) and potassium carbonate (171 mg, 800 mumol). The resulting mixture was heated under argon at 90 C. with stirring for 2 h. The mixture was then cooled, diluted with dichloromethane (10 mL), dried with sodium sulfate and concentrated under reduced pressure. Flash chromatography (ISCO system, silica, 0-50% ethyl acetate in hexane) provided 15 (19.6 mg, 12%) as a solid: LRESIMS m/z 294.1 [M+H]+, calcd. for C11H9Br1N3O2 294.0.

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; CalciMedica, Inc.; US2011/263612; (2011); A1;,
Bromide – Wikipedia,
bromide – Wiktionary

Application of 5279-32-3, 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. 5279-32-3 name is 5,6-Dibromobenzo[d][1,3]dioxole, 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.

Method B: 4-Amino-1-(4-methoxybenzyl)-1H-imidazo[4,5-c]pyridine-2-thiol (100 mg, 0.349 mmol), 5,6-dibromo-1,3-benzodioxole (196 mg, 0.698 mmol), Pd2dba3 (16 mg, 1.8×10-2 mmol), Xantphos (21 mg, 3.5×10-2 mmol), and Cs2CO3 (227 mg, 0.698 mmol) were placed in a vial and degassed dioxane (1.2 mL) was added to the mixture. After heating at 100 C. for 10 h, the mixture was diluted with EA, washed with brine, dried (Na2SO4), filtered, and concentrated in vacuum. The residue was purified by column chromatography (SiO2, MeOH/CH2Cl2, 0 to 10%) to afford the title compound (54 mg, 31%).

At the same time, in my other blogs, there are other synthetic methods of this type of compound, 5,6-Dibromobenzo[d][1,3]dioxole, and friends who are interested can also refer to it.

Reference:
Patent; Myrexis, Inc.; US8017780; (2011); B1;,
Bromide – Wikipedia,
bromide – Wiktionary

Some common heterocyclic compound, 5279-32-3, name is 5,6-Dibromobenzo[d][1,3]dioxole, molecular formula is C7H4Br2O2, 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. Safety of 5,6-Dibromobenzo[d][1,3]dioxole

Under nitrogen atmosphere, 5,6-Dibromo-1,3-benzodioxole (13a, 1.58 g, 5.64 mmol), zinc(II)cyanide (670 mg, 5.71 mmol) and [1,1?-bis(diphenylphosphino)ferrocene]dichloropalladium(II) (208 mg, 284 mumol) were dissolved in anhydrous dimethylacetamide (12 mL) andstirred for 3 h at 150 C. Subsequently, the mixture was diluted with ethyl acetate (50 mL),washed with water (2 × 50 mL), the organic layer dried over magnesium sulfate and the solventremoved in vacuo. The crude product was purified by column chromatography using silica anddichloromethane as eluent (Rf = 0.50) to obtain a colourless solid (829 mg, 4.82 mmol, 85%).1H NMR (500MHz, CDCl3, 300 K): delta = 7.14 (s, 2H), 6.21 (s, 2H) ppm;13C NMR (125 MHz, CDCl3, 300 K): delta = 151.7 (2C), 115.5 (2C), 112.8 (2C), 111.0 (2C), 104.0 ppm;MS (EI, 70 eV): m/z (%) = 172 (100) [M]+;HR-MS (EI, 70 eV): m/z = calcd. for C9H4N2O2 [M]+ 172.0267, found 172.0273.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 5279-32-3, its application will become more common.

Reference:
Article; Hamer, Sebastian; Roehricht, Fynn; Jakoby, Marius; Howard, Ian A.; Zhang, Xianghui; Naether, Christian; Herges, Rainer; Beilstein Journal of Organic Chemistry; vol. 15; (2019); p. 1331 – 1338;,
Bromide – Wikipedia,
bromide – Wiktionary

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. 5279-32-3, name is 5,6-Dibromobenzo[d][1,3]dioxole, A new synthetic method of this compound is introduced below., Application In Synthesis of 5,6-Dibromobenzo[d][1,3]dioxole

Step 1 5-(4-fluorophenyl)-6-[4-(methylthio)phenyl]-1,3-benzodioxole Under nitrogen, 1 g of Pd(PPh3)4 was added to a stirred solution of 4 g (14.3 mmol) of 5,6-dibromo-1,3-benzodioxole (Lancaster), 2.4 g (17.2 mmol) of 4-fluorophenyl boronic acid, and 2.87 g (17.2 mmol) of 4-methylthiophenylboronic acid (Example 1, Step 2) in 70 mL of toluene, 40 mL of ethanol, and 30 mL of 2M Na2 CO3. After vigorous stirring at reflux overnight, the solvent was removed in vacuo. The residue was dissolved in ethyl acetate, washed with water, and dried over Na2 SO4. Concentration in vacuo gave 6.9 g of 5-(4-fluorophenyl)-6-[4-(methylthio)phenyl]-1,3-benzodioxole as a semi-solid which was used without further purification.

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; G.D. Searle & Co.; US5739166; (1998); A;,
Bromide – Wikipedia,
bromide – Wiktionary

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. 5279-32-3, name is 5,6-Dibromobenzo[d][1,3]dioxole, A new synthetic method of this compound is introduced below., name: 5,6-Dibromobenzo[d][1,3]dioxole

Step 1 Preparation of 5-bromo-6-(4-fluorophenyl)-1,3-benzodioxole Under nitrogen, 1.1 g of Pd(PPh3)4 was added to a stirred solution of 10.4 g (37.2 mmol) of 5,6-dibromo-1,3-benzodioxole and 2.6 g (18.6 mmol) of 4-fluorophenylboronic acid in 100 mL of toluene, 60 mL of ethanol, and 40 mL of M Na2 CO3. After vigorous stirring at reflux overnight, the solvent was removed in vacuo. The residue was dissolved in ethyl acetate, washed with water, and dried over Na2 SO4. Purification by silica gel chromatography (Waters Prep-500A) with hexane as the eluent gave 3.9 g (71%) of 5-bromo-6 (4-fluorophenyl)-1,3-benzodioxole as a colorless solid: mp 86.0-87.5 C.; NMR (CDCl3) delta 6.02 (s, H), 6.77 (s, 1H), 7.04-7.13 (m, 3H), 7.28-7.35 (m, 2H).

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; G.D. Searle & Co.; US5739166; (1998); A;,
Bromide – Wikipedia,
bromide – Wiktionary

Reference of 5279-32-3, A common heterocyclic compound, 5279-32-3, name is 5,6-Dibromobenzo[d][1,3]dioxole, molecular formula is C7H4Br2O2, 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 12 mL vial was charged with Pd(OAc)2 (2 mol%), BuPAd2 (6 mol%), and a stirring bar. Then, 2 ml dioxane and 1 mmol of bromobenzene were injected by syringe. The vial (or several vials) was placed in an alloy plate, which was transferred into a 300 mL autoclave of the 4560 series from Parr Instruments under argon atmosphere. After flushing the autoclave three times with NH3, a pressure of 2 bar NH3 and 2 bar CO was adjusted at ambient temperature. Then, the reaction was performed for 16 hours at 100 oC. After the reaction is finished, the autoclave was cooled down to room temperature and the pressure was released carefully. Then, CuI (5 mol%), DMEDA (10%), K2CO3 (3 mmol) and 1,2-dibromobenzene were added in under air, the vial was closed and heated to 110oC for 20 hours. The reaction mixture cooled down to room temperature. The solution was extracted 3-5 times with 2-3 ml of ethyl acetate from aqua solution. After evaporation of the organic solvent the residue was adsorbed on silica gel and the crude product was purified by column chromatography using n-heptane/AcOEt (20:1) as eluent.

The synthetic route of 5279-32-3 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Wu, Xiao-Feng; Neumann, Helfried; Neumann, Stephan; Beller, Matthias; Tetrahedron Letters; vol. 54; 24; (2013); p. 3040 – 3042;,
Bromide – Wikipedia,
bromide – Wiktionary

Reference of 5279-32-3,Some common heterocyclic compound, 5279-32-3, name is 5,6-Dibromobenzo[d][1,3]dioxole, molecular formula is C7H4Br2O2, 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 suspension of 5-amino-2-mercapto-1 -methyl-1 H-imidazole-4-carboxamide (ChemBridge, 0.393 g, 2.28 mmol), 1 ,2-dibromo-4,5-(methylenedioxy) benzene (1.28 g, 4.57 mmol), t-BuOK (0.258 g, 2.30 mmol), (oxydi-2,1 – phenylene)-bis(diphenylphosphine) (0.122 g, 0.228 mmol) and Pd2(dba)3 (0.209 g, 0.228 mmol) in DMF (15 ml_) was warmed up to 100 0C, and allowed to react for 5 h. Solvent was concentrated off and the crude residue was purified by flash chromatography on SiO2 (10% MeOH/CH2CI2/NH3) to furnish 5-amino-2-[(6-bromo-1 ,3-benzodioxol-5-yl)thio]-1 -methyl-1 H-imidazole-4- carboxamide (0.519 g, off-white solid, yield: 61 %). 1H NMR (DMSO-d6, 250 MHz) delta ppm: 7.28(s, 1 H), 7.08 (bs, 1 H), 6.77 (bs, 1 H), 6.14 (bs, 2H), 6.13 (s, 1 H), 6.04 (s, 2H), 3.30 (s, 3H). El MS: m/z = 371 (M+1 ).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 5,6-Dibromobenzo[d][1,3]dioxole, its application will become more common.

Reference:
Patent; CRYSTAX PHARMACEUTICALS, S.L.; WO2009/7399; (2009); A1;,
Bromide – Wikipedia,
bromide – Wiktionary

Synthetic Route of 5279-32-3, 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. 5279-32-3, name is 5,6-Dibromobenzo[d][1,3]dioxole belongs to bromides-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below.

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, 5,6-Dibromobenzo[d][1,3]dioxole, 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;,
Bromide – Wikipedia,
bromide – Wiktionary