Category: 1073-39-8

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. 1073-39-8, name is 3-Bromobicyclo[4.2.0]octa-1,3,5-triene, A new synthetic method of this compound is introduced below., name: 3-Bromobicyclo[4.2.0]octa-1,3,5-triene

4-bromobenzocyclobutene[4-bromobenzocyclobutene] (4.23 mL, 34 mmol) was dissolved in tetrahydrofuran[THF] (100 mL) and then charged into a dry ice / acetone bath [dry ice/acetone bath] to lower the furnace temperature.n-BuLi (13 mL, 32 mmol, 2.5 M in hexane) was slowly added and stirred for 1 hour.Then 9-fluorenone [9-fluorenone](3.6 g, 20 mmol) was added thereto, followed by stirring overnight.The reaction was stopped with water and extracted with ethyl acetate water.After the organic layer was collected, the organic layer was dried and filtered using MgSO4.The filtrate was dried with a vacuum rotary concentrator to remove the organic solvent,The residue was column purified to give 4.32 g (76% yield) of intermediate 1-1.

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; LG Chem, Ltd.; Seo Min-seop; Lee Jae-cheol; Kim Jin-seok; Bae Jae-sun; Kim Byeong-jae; (47 pag.)KR2019/60484; (2019); A;,
Bromide – Wikipedia,
bromide – Wiktionary

Some common heterocyclic compound, 1073-39-8, name is 3-Bromobicyclo[4.2.0]octa-1,3,5-triene, molecular formula is C8H7Br, 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: C8H7Br

The synthesis of a tetracene brominated in the 2-position is shown by way of example in the following illustration: In a first step, alpha-chloro-o-xylene 1 was subjected to pyrolysis at approximately 800 C. and 0.5 mbar. Benzocyclobutene 2 was obtained in a 45% yield. The selective bromination thereof was carried out by treating benzocyclobutene, dissolved in acetic acid, with a mixture of bromine and iodine at room temperature, resulting in 4-bromobenzocyclobutene 3. Dissolving in toluene and heating with a slight molar excess of 1,4-dihydro-1,4-epoxynaphthalene 4 at 220 C. for 20 hours resulted in an 80% yield of a pure endo/exo mixture of the Diels-Alder addition product 5, a colorless crystalline material. This material was heated at reflux in acetic anhydride in the presence of concentrated hydrochloric acid, thus forming 9-bromo-6,11-dihydrotetracene 6. The Yamamoto coupling then resulted in 2-(5,12-dihydrotetracene-2-yl)-5,12-dihydrotetracene 7. The coupling reaction was carried out in an approximately 80% yield in a mixture of dimethylformamide and toluene at 80 C., using bis(cyclooctadienyl) nickel(0) in stoichiometric quantities. After recrystallization from o-dichlorobenzene, compound 7 was dehydrogenated by treatment with 2,3-dichloro-5,6-dicyano-p-benzoquinone (DDQ) in boiling o-xylene. After purification by repeated vacuum sublimation, orange-red crystals of 2-(tetracene-2-yl) tetracene 8 were obtained in a yield of 75%. All intermediate products were characterized by 1H and 13C NMR spectroscopy and mass spectroscopy. Compound 8 was characterized by UV-visible spectroscopy.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 1073-39-8, its application will become more common.

Reference:
Patent; Rehahn, Matthias; Roth, Michael; Von Seggern, Heinz; Schmechel, Roland; Ahles, Marcus; US2008/214838; (2008); A1;,
Bromide – Wikipedia,
bromide – Wiktionary

Application of 1073-39-8, 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. 1073-39-8, name is 3-Bromobicyclo[4.2.0]octa-1,3,5-triene belongs to bromides-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below.

20 g (109 mmol) 2-(4-Bromophenyl)-cyclobutyl was dissolved in 150 ml dry THF and cooled to -78 C. 44 ml (109 mmol, 2.5 M solution) of n-Buli was added dropwise and the solution was stirred for one hour at -78 C. 2′- Bromo-biphenyl-2-carboxylic acid (43.6 mmol, 12.7 g) was dissolved in 25 ml THF and added to the n-BuLi solution at -78 C. The reaction mixture was stirred for 1 h at -78 C and then warmed to RT over the weekend. (0187) Ammoniumchloride solution was added to quench the reaction and the mixture was extracted with ethyl acetate. The combined organic phases were dried and the solvent was evaporated in vacuo. The resulting crude product was dissolved in 60 ml dry Toluene and 60 ml Hydrochloric acid (37%) as well as 1 15 ml acetic acid was added. The reaction was stirred at 80 C over night. After cooling down to RT the water was added, the aqueous phase was extracted with toluene and the combined organic phases were washed with water and dried with Na2SO4. The solvent was removed in vacuo. The resulting solid was recrystallized in (0188) Heptane/Toluene. 16 was obtained as a white product with 85% yield (0189) (37.1 mmol, 16.6 g). (0190) 5 I6 (15 g, 33.4 mmol), o-biphenylamine (6.2 g, 36.7 mmol) and Sodium-f- butylate (10.6 g, 1 10 mmol) were dissolved in 200 ml toluene. The mixture was degassed for 15 minutes and subsequently Pd(dppf)CI2 (1 .8 g, 2.2 (0191) mmol) was added. The solution was heated at reflux for 4 hours and then (0192) ^ Q cooled to RT. The mixture was filtered over Alox using toluene as the (0193) solvent. The resulting solid was recrystallized from toluene/heptanes. I7 was obtained as a white solid with a yield of 63% (1 1 .3 g, 21 mmol). (0194) 4.7 g (8.5 mmol) 2,7-dibromo-9,9-dioctyl-fluorene and 10 g (18.6 mmol, 2.2 1 eq) 17 were added to 100 ml Toluene. Subsequently 1 .5 g (1 .7 mmol, 0.2 (0195) eq) Pd2dba3 and 1 .6 g (17 mmol, 2 eq) Sodium-f-butylate were added and the mixture was degassed with argon. After 5 min degassing 3.8 g (1 .7 (0196) mmol, 0.2 eq) tri-f-butylphosphine was added and the reaction was stirred at reflux over the weekend. After cooling to RT the mixture was filtered over (0197) 20 (0198) Celite and subsequently purified via Soxhlet using Toluene as the solvent. (0199) The resulting solid was purified via flash chromatography. 9.7 g (6.6 mmol, 78%) of P8 was obtained.

The synthetic route of 3-Bromobicyclo[4.2.0]octa-1,3,5-triene has been constantly updated, and we look forward to future research findings.

Reference:
Patent; MERCK PATENT GMBH; SCHEIBLE, Katja Maria; ECKES, Fabrice; HEIL, Holger; BURKHART, Beate; JOOSTEN, Dominik; MONTENEGRO, Elvira; (93 pag.)WO2018/65357; (2018); A1;,
Bromide – Wikipedia,
bromide – Wiktionary

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. 1073-39-8, name is 3-Bromobicyclo[4.2.0]octa-1,3,5-triene belongs to bromides-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below. HPLC of Formula: C8H7Br

3-Carboxaldehydebicyclo[4,2,0]octa- 1 ,3;5-triene or A- Carboxaldehydebenzocyclobutene, Q6. To a 500-mL flask was added ’50 mL dry of THF, Mg turnings (2.88 g, 120 mmol), and 1,2-dibromoethane (4 drops). The reaction mixture was then heated under reflux for 15 min, 4-Bromobenzocyclobutene, 5,1 1 (20.0 g, 109 mmol) in 25 mL THF was added via a dropping funnel to form the Grignard reagent. After addition and rinsing the dropping funnel with 25 mL of dry THF, the reaction mixture was heated for an additional 45 min under reflux to give a green brown solution. The reaction mixture was then cooled to 0 0C, DMF (15 mL, 210 mmol) was added dropwise to the solution, and the reaction mixture was heated under reflux for 15 min. The reaction mixture was poured onto 150 g of ice, acidified to pH), and neutralized with saturated NaHCO3 solution. The crude product was extracted with ethyl acetate, the organic phase was filtered over Celite, and evaporation of the solvent gave the crude product. The product was purified by column chromatography using 10% diethyl ether/hexane as eluting solvents and was finally purified by Kugelrohr distillation (145 0C, 0.5 mm) to give the aldehyde Q6 (1 1.7 g, 81.2%) as a colorless liquid; IR 3000-2800, 1690, 1598, 1216, 1067 and 827 CnV1; 1H NMR (400 MHz, CDCl3) delta 9.9 (s, IH, CHO), 7.65 (dd, IH, J= 7.4 Hz, J= 1.2 Hz, ArH), 7:50 (s, IH, ArH), 7.14 (dd, IH, J =7.4 Hz, J) 1.2 Hz, ArH), 3.15 (s, 4H, CH2); 13C NMR (100 MHz, CDCl3) «5 192.28, 153.69, 146.57, 135.4, 130.26, 122.89, 122.81, 29.97, and 29.23. Anal. Calcd for C9H8O; C, 81.8; H 6.10. Found: C, 81.7; H, 5.94.

The synthetic route of 1073-39-8 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; VANDERBILT UNIVERSITY; WO2008/24435; (2008); A2;,
Bromide – Wikipedia,
bromide – Wiktionary

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. 1073-39-8, name is 3-Bromobicyclo[4.2.0]octa-1,3,5-triene, This compound has unique chemical properties. The synthetic route is as follows., Formula: C8H7Br

To 4-bromobicyclo[4.2.0]octa-1,3,5-triene (1, 3.25 g, 7,76 mmol) in dioxane (30 mL) were added tert-butyl carbamate (2.53 g, 21.6 mmol), cesium carbonate (9.2 g, 28.24 mmol), 4,5-bis(diphenylphosphino)-9,9-dimethylxanthene (O.5g, 0.86 mmol), andtris(dib enzylideneacetone)dipalladium-chloroform adduct (0.3 g, 0.29 mmol). The reaction mixture was stirred at 105 C under nitrogen overnight. The reaction mixture was poured into water, and extracted with ethyl acetate. The organic layer was washed with brine, dried over sodium sulfate, and filtered. The filtrate was concentrated, and purified with silica gel column chromatography eluting with 20% to 100% ethyl acetate in hexane to give product (2).

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 1073-39-8.

Reference:
Patent; PLEXXIKON INC.; ZHANG, Jiazhong; POWERS, Hanna; ALBERS, Aaron; PHAM, Phuongly; WU, Guoxian; BUELL, John; SPEVAK, Wayne; (449 pag.)WO2018/57973; (2018); A1;,
Bromide – Wikipedia,
bromide – Wiktionary

1073-39-8, name is 3-Bromobicyclo[4.2.0]octa-1,3,5-triene, belongs to bromides-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. Safety of 3-Bromobicyclo[4.2.0]octa-1,3,5-triene

To a mixture of 3-bromobicyclo[4.2.0]octa-1,3,5-triene (309.3 mg, 1.69 mmol, 1.20 equiv) in tetrahydrofuran (12 mL) was added n-BuLi (0.68 mL, 1.20 equiv, 2.5 M in hexane) dropwise at -78C. The solution was stirred for 30 min at -78C. To the resulting mixture was then added a solution of 5-bromo-2- ethylbenzaldehyde (300 mg, 1.41 mmol, 1.00 equiv) in tetrahydrofuran (3 mL) dropwise at -78C. The reaction mixture was stirred for 2 h at -78C. NH4CI/H20 was added and the mixture was extracted with ethyl acetate three times. The combined extracts were washed with brine and dried over Na2S04, then concentrated and purified by chromatography on silica gel (1 :5 EA/PE) to yield bicyclo[4.2.0]octa-1 (6),2,4-trien-3-yl(5-bromo-2-ethylphenyl)methanol as a yellow oil. MS (ES) m/z: 299.0, 301.0[M-OH]+.

The synthetic route of 1073-39-8 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; JANSSEN PHARMACEUTICA NV; GAUL, Micheal; KUO, Gee-Hong; XU, Guozhang; LIANG, Yin; (218 pag.)WO2018/89449; (2018); A1;,
Bromide – Wikipedia,
bromide – Wiktionary

Synthetic Route of 1073-39-8, 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. 1073-39-8, name is 3-Bromobicyclo[4.2.0]octa-1,3,5-triene belongs to bromides-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below.

To a mixture of 3-bromobicyclo[4.2.0]octa-1,3,5-triene (385 mg, 2.10 mmol, 1.20 equiv) in tetrahydrofuran (7 ml) was added n-BuLi (2.5M in hexane, 0.77 ml, 1.10 equiv) dropwise at -78C, and the reaction mixture was stirred for 30 min at -78C. 5-Bromo-2-(dimethylamino)benzaldehyde (400 mg, 1.75 mmol, 1.00 equiv) in tetrahydrofuran (3 ml) was then added to the solution. The reaction mixture was stirred at -78C for 2 h. NH4CI/H20 was added and the mixture was extracted with EtOAc thrice. The combined extracts were washed with brine and dried over Na2S04, then concentrated and purified by chromatography on silica gel (20% EA/PE) to yield bicyclo[4.2.0]octa-1 (6),2,4-trien-3-yl[5-bromo-2- (dimethylamino)phenyl]methanol as a light yellow oil. MS (ES) m/z: 332.0 [M+H]+

The synthetic route of 3-Bromobicyclo[4.2.0]octa-1,3,5-triene has been constantly updated, and we look forward to future research findings.

Reference:
Patent; JANSSEN PHARMACEUTICA NV; GAUL, Micheal; KUO, Gee-Hong; XU, Guozhang; LIANG, Yin; (218 pag.)WO2018/89449; (2018); A1;,
Bromide – Wikipedia,
bromide – Wiktionary

Synthetic Route of 1073-39-8, 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. 1073-39-8, name is 3-Bromobicyclo[4.2.0]octa-1,3,5-triene belongs to bromides-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below.

To a mixture of 3-bromobicyclo[4.2.0]octa-1,3,5-triene (1 17 mg, 0.64 mmol) in THF (2 ml) was added dropwise n-BuLi (2.5 M in n-hexane) (0.25 ml, 0.64 mmol) at -78 C under N2. The reaction mixture was stirred at -78C for 30 min. 4-(benzyloxy)-2-methyl-3-((2S,3S,4R,5R,6R)-3,4,5-tris(benzyloxy)-6- (benzyloxymethyl)-tetrahydro-2H-pyran-2-yl)benzaldehyde ((240 mg, 0.32 mmol) in THF (1 ml) was added dropwise at -78C. The reaction mixture was stirred at -78C for 1 h. Saturated NH4CI (aq) was added and the mixture was extracted with EA thrice. The combined extracts were washed with water, saturated brine and dried over anhydrous Na2S04, then concentrated and purified by chromatography on silica gel (1 :3 EA/PE) to (4-(benzyloxy)-2- methyl-3-((2S,3S,4R,5R,6R)-3,4,5-tris(benzyloxy)-6-(benzyloxymethyl)- tetrahydro-2H-pyran-2-yl)phenyl)(1,2-dihydrocyclo-butabenzen-4-yl)methanol as a yellow oil. MS (ES) m/z: 875.5 [M+Na]+.

The synthetic route of 3-Bromobicyclo[4.2.0]octa-1,3,5-triene has been constantly updated, and we look forward to future research findings.

Reference:
Patent; JANSSEN PHARMACEUTICA NV; GAUL, Micheal; KUO, Gee-Hong; XU, Guozhang; LIANG, Yin; (218 pag.)WO2018/89449; (2018); A1;,
Bromide – Wikipedia,
bromide – Wiktionary

1073-39-8, name is 3-Bromobicyclo[4.2.0]octa-1,3,5-triene, belongs to bromides-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. Recommanded Product: 3-Bromobicyclo[4.2.0]octa-1,3,5-triene

To a mixture of 3-bromobicyclo[4.2.0]octa-1,3,5-triene (1092.9 mg, 5.97 mmol) THF (4 mL) was added, cooled to -78 C and the flask was evacuated, re-filled with nitrogen. To the mixture was added 3.7 ml of n-BuLi (3.7 ml, 5.97 mmol, 1.6 M in hexane) dropwise with stirring at -78 C for 25 min. 4- (Benzyloxy)-5-bromo-2-methylbenzaldehyde (1.82 g, 5.97 mmol) in THF (6 mL) was then added to the solution and the mixture was kept stirring for 1 h at -78 C. The resulting mixture was quenched with aqueous NH4CI (15 ml), extracted with EtOAc three times (20 ml each time). The combined extracts were washed with brine, dried over Na2S04, filtered and concentrated. The residue was purified by flash column chromatography on silica gel (40 g, EtOAc/heptane: 0>10%) to yield (4-(benzyloxy)-5-bromo-2- methylphenyl)(bicyclo[4.2.0]octa-1 (6),2,4-trien-3-yl)methanol as a colorless oil. MS (ES) m/z: 431.10 [M+Na]+.

The synthetic route of 1073-39-8 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; JANSSEN PHARMACEUTICA NV; GAUL, Micheal; KUO, Gee-Hong; XU, Guozhang; LIANG, Yin; (218 pag.)WO2018/89449; (2018); A1;,
Bromide – Wikipedia,
bromide – Wiktionary

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. 1073-39-8, name is 3-Bromobicyclo[4.2.0]octa-1,3,5-triene, This compound has unique chemical properties. The synthetic route is as follows., SDS of cas: 1073-39-8

General procedure: In a 100 mL round-bottom flask, 1,2-dibromoethane (0.3 mL), magnesium (1.9 g, 80 mmol), and dry THF (5 mL) were added and stirred at ambient temperature for 30 min under nitrogen. Then 3-chloropropylmethyldichlorosilane (9.5 mL, 60 mmol) in THF(45 mL) was added dropwise over a period of 15 min and the reaction mixture was heated to 50 C for another 2 h. In another flask, magnesium (1.44 g, 60 mmol) and a grain of iodine were added. Then 4-bromobenzocyclobutene (9.15 g, 50 mmol) in 30 mL of dry THF was slowly added dropwise over a period of 2 h under nitrogen atmosphere. The reaction mixture was heated to 50 C and stirred continuously for 1 h. Resulted solution was added to the first flask. The reaction temperature was elevated to 50 C and kept overnight. Then the solution was poured into 1 M aq. HCl and extracted with hexane. The organic layer was washed twice with water and dried over anhydrous sodium sulfate. After removing the solvents by rotary evaporation, the residual oil was purified by silica-gel column chromatography (petroleum ether) to give the colorless oil (30.5 mmol, 5.74 g) in 61% yield.

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 1073-39-8.

Reference:
Article; Hu, Huan; Liu, Lili; Li, Zheng; Zhao, Cuijiao; Huang, Yawen; Chang, Guanjun; Yang, Junxiao; Polymer; vol. 66; (2015); p. 58 – 66;,
Bromide – Wikipedia,
bromide – Wiktionary