Author: Jessica.F

Electric Literature of 626-39-1, These common heterocyclic compound, 626-39-1, name is 1,3,5-Tribromobenzene, 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.

[0372] 1,3,5-Tribromo-benzene (31.4 g, 100 mmol) was dissolved under argon in a flame dried three-neck flask in 1000 mL diethylether and the solution was cooled to -72C. A solution of 62 mL r°BuLi (1.6 M in hexane, 100 mmol) was added to the resulting suspension in such a fashion that temperature did not rise above -7O0C. The mixture was stirred for 30 min at -750C and the reaction was monitored by HPLC. A solution of 10.4 g (100 mmol) 3-cyanopyridine in 100 mL diethylether was added in such a fashion that temperature did not rise above -710C. The mixture was stirred at -75C for 60 min and the reaction was monitored by HPLC. The cooling bath was removed and warmed to -250C. 2 N HCl (250 mL) was added and the mixture was stirred for 20 min at room temperature. The mixture was made alkaline by addition of 1 N NaOH. The product was extracted with ethyl acetate and the combined organic layers were dried over Na2SO4. The product was purified by chromatography (700 g silica agel, CH2Cl2, then CH2Cl2 / ethyl acetate 1:1, UV) to yield 27.7 g (81 %) of (3,5-dibromo-rhohenyl)-pyridin-3-yl-methanone.

The synthetic route of 626-39-1 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; LOCUS PHARMACEUTICALS, INC.; WO2008/8059; (2008); A1;,
Bromide – Wikipedia,
bromide – Wiktionary

Application of 327-51-5, These common heterocyclic compound, 327-51-5, name is 1,4-Dibromo-2,5-difluorobenzene, 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 i-7: methyl 5-fluoro-2-methoxy-4-(4,4,5,5-tetramethyl-l,3,2-dioxa borolan-2-yl)benzoate (i-7)Scheme i-7.i-7 i) Preparation of 4-bromo-2,5-difluorobenzoic acid (i-7b)To a solution of l,4-dibromo-2,5-difluorobenzene (i-7a) (1.1 g , 4 mmol) in Et20 (10 mL) at – 78 C was added n-BuLi (2.5M in hexane, 1.6 mL, 4 mmol) dropwise. The mixture was stirred for 30 min at -78 C and then quenched with an excess of freshly crushed dry ice. After 15 min, the mixture was brought to rt and diluted with H20. The aqueous layer was separated, and the organic layer was extracted with 10% aq. Na2C03. The combined aqueous layers were acidified with 1M HC1 and extracted with EtOAc. The combined organic layers were dried with Na2S04 and concentrated to give the title compound. LCMS (ESI) calc’d for C7H3BrF202 [M+H]+: 237, found: 237

The synthetic route of 327-51-5 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; MERCK SHARP & DOHME CORP.; N.V. ORGANON; KARSTENS, Willem Frederik Johan; STELT, Mario van der; CALS, Jos; AZEVEDO, Rita Corte Real Goncalves; BARR, Kenneth Jay; ZHANG, Hongjun; BERESIS, Richard Thomas; ZHANG, Dongshan; DUAN, Xiaobang; WO2012/106995; (2012); A1;,
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. 4263-52-9, name is Sodium 2-bromoethanesulphonate, A new synthetic method of this compound is introduced below., HPLC of Formula: C2H4BrNaO3S

44.6 g of isophorone diisocyanate (IPDI) was added in a mechanically agitated round-bottom flask. 0.2 mL of catalyst dibutyltin dilaurate was added in the IPDI, and 17.8 g of dimethyl ethanolamine (HO CH2CH2N(CH3)2) was added dropwise in the IPDI while stirring at 30 C. using a dropping funnel to form a reaction mixture. The reaction mixture reacted for 1 hr, and then was stirred to react for 12 hrs at 30 C. 42.2 g of 2-bromoethyl sodium sulfonate which was dissolved in 400 mL of anhydrous tetrahydrofuran was added dropwise in the reaction mixture and reacted for 1 hr to yield a white precipitate. The white precipitate was centrifugalized several times to yield the isocyanate-terminated betaine compound.

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; Shenzhen University; CHEN, Shiguo; YUAN, Lingjun; ZHU, Xingli; CHEN, Shaojun; GE, Zaochuan; (11 pag.)US2017/339960; (2017); A1;,
Bromide – Wikipedia,
bromide – Wiktionary

Application of 960203-41-2, A common heterocyclic compound, 960203-41-2, name is (2-Bromophenyl)(2,4-dimethylphenyl)sulfane, molecular formula is C14H13BrS, 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.

2.1 g of the compound C synthesized in Example 1 was charged into a 100 mL three-necked flask, and 0.9 g of piperazine, 0.3 g of cuprous iodide, 0.5 g of 2-acetylcyclohexanone and 3.0 g of potassium carbonate of 100 to 200 mesh were weighed into a flask, The amount of 50mL DMF into the flask,The reaction mixture was heated to reflux. TLC was used to detect the reaction. The reaction was complete with 100 mL of ethyl acetate and 150 mL of water. The filtrate was separated by suction filtration and the organic phase was washed twice with 100 mL of water. The organic phase was washed with anhydrous sulfuric acid After drying for 2 h, the oil was concentrated at 45 ° C to obtain an oil. After 30 mL of n-hexane was added to the oil, the mixture was stirred and crystallized for 3 h. After filtration, the filter cake was washed twice with a little solvent and the cake was vacuum dried at 40 ° C for 12 h. Brown solid product 2.2 g, yield 81.5percent.

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; Beijing Wanquan German public medicine Biotechnology Co., Ltd; Xu, Yong; Zhao, Guolei; (6 pag.)CN105367516; (2016); A;,
Bromide – Wikipedia,
bromide – Wiktionary

Synthetic Route of 2695-47-8, 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. 2695-47-8, name is 6-Bromo-1-hexene belongs to bromides-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below.

To a two-neck oven-dried 250-mL round-bottom flask, 3,6-di(thiophen-2-yl)-2,5-dihydropyrrolo[3,4-c]pyrrole-1,4-dione(3.7 g, 12.2 mmol) and anhydrous K2CO3 (4.2 g, 30.5 mmol) were added. The reaction system was then evacuated and refilled with N2 before anhydrous DMF (50 mL) was injected by asyringe. After stirring and heating at 120C for 1 h, the temperatureof reaction mixture was decreased to 100C, after which6-bromohex-1-ene (5.0 g, 30.5 mmol) was added dropwise, and the reaction mixture was maintained at 100C with stirring for 2 days. After the reaction mixture was cooled to room temperature, it was poured into cold water and stirred for 30 min. The organic phase was extracted with dichloromethane, dried over anhydrous MgSO4, and then the crude product was subjected to column chromatography with hexane and chloroform as eluent. Additionally, a simple recrystallization from CHCl3/ethanol offered pure purple crystals (3.7 g, 65 %). deltaH (CDCl3, 400 MHz)8.90 (2H, d, J 3.6), 7.70 (2H, d, J 4.8), 7.31 (2H, t, J 4.8), 5.78-5.89 (2H, m), 4.49-5.04 (4H, m), 4.09 (4H, t, J 7.6), 2.09-2.15(4H, m), 1.72-1.79 (4H, m), 1.48-1.56 (6H, m).

The synthetic route of 6-Bromo-1-hexene has been constantly updated, and we look forward to future research findings.

Reference:
Article; Shi, Zugui; Neo, Wei Teng; Zhou, Hui; Xu, Jianwei; Australian Journal of Chemistry; vol. 69; 4; (2016); p. 403 – 410;,
Bromide – Wikipedia,
bromide – Wiktionary

Electric Literature of 2789-89-1, A common heterocyclic compound, 2789-89-1, name is 1,2-Bis(4-bromophenyl)ethyne, molecular formula is C14H8Br2, 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.

To a solution of di(4-bromophenyl)acetylene (719 mg, 2.14 mmol, 1 equiv) in dry THF (60 mL) was added the fresh solution (Ca. 0.4 mol/L) of (4-dodecylphenyl)magnesium bromide (20 mL, 8.57 mmol, 4 equiv) in a flame-dried apparatus. PdCI2(dppf) (138 mg,0.17 mmol, 8 mol%) was then added and the reaction mixture was stirred at reflux under argon overnight. The solution was then cooled down to room temperature. The obtained white precipitate was filtered and washed with methanol and petroleum ether. 044 was obtained as an off-white solid (1.1672 mg, 82%).

The synthetic route of 2789-89-1 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; THE UNIVERSITY OF BIRMINGHAM; BARANOFF, Etienne David; HERBAUT, Antoine Joel Maurice; (37 pag.)WO2016/193748; (2016); A1;,
Bromide – Wikipedia,
bromide – Wiktionary

These common heterocyclic compound, 69321-60-4, name is 2,6-Dibromotoluene, 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. HPLC of Formula: C7H6Br2

To a solution of 1 , 3-dibromo-2-methylbenzene (3 g, 12.00 mmol) in Tetrahydrofuran (THF) (100 mL) stirred under nitrogen at -78 C was added BuLi (9.00 mL, 14.40 mmol) dropwise. The reaction mixture was stirred at -78 C for 20 min. DMF (1.1 15 mL, 14.40 mmol) was added dropwise. The reaction mixture was continuously stirred for 2 hours. The reaction was quenched with sat. aq. ammonia chloride solution. The aqueous layers were seperated and extracted by EA for 3 times. The combined organic layers were washed by brine, dried over anhydrous sodium sulfate. The dried solution was concentrated in vacuo to afford 3-bromo-2-methylbenzaldehyde (D93) (2.4g), which was used for the next step without further purification. MS (ES):C8H7BrO requires 197.9; found 199 (M+H+)

The synthetic route of 2,6-Dibromotoluene has been constantly updated, and we look forward to future research findings.

Reference:
Patent; GLAXO GROUP LIMITED; DENG, Guanghui; LIN, Xichen; REN, Feng; ZHAO, Baowei; WO2011/134280; (2011); A1;,
Bromide – Wikipedia,
bromide – Wiktionary

Electric Literature of 103-64-0, The chemical industry reduces the impact on the environment during synthesis 103-64-0, name is (2-Bromovinyl)benzene, I believe this compound will play a more active role in future production and life.

General procedure: A round-bottom flask was charged with phenylacetylene(1.5 mmol, 0.16 mL), NaOH (1.5 mmol, 100 mg), PEG200(2 mL), and aryl halide (1.0 mmol). To this mixture,3.0 mol% of PdCl2 and 8.0 mol% of DPPPEG200 wereadded. The reaction mixture was placed in an 80 C oilbath and stirred to complete. The completion of the reactionwas monitored by TLC. After completion of reaction,the mixture was cooled to room temperature, and the catalystwas removed by addition of Et2O and then centrifugated.The isolated catalyst was dried and reused. Thefiltered solution was evaporated reduced pressure, and theexpected product was purified by column chromatographyover silica gel [60 Merck (230-240 mesh)] using petroleumether/ethyl acetate (5:1) as eluent to afford the product withhigh purity in 58-95 % yield.

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, (2-Bromovinyl)benzene, other downstream synthetic routes, hurry up and to see.

Reference:
Article; Iranpoor, Nasser; Firouzabadi, Habib; Riazi, Asma; Journal of the Iranian Chemical Society; vol. 12; 1; (2015); p. 155 – 165;,
Bromide – Wikipedia,
bromide – Wiktionary

Synthetic Route of 937046-98-5, A common heterocyclic compound, 937046-98-5, name is 7-Bromopyrrolo[2,1-f][1,2,4]triazin-4-amine, molecular formula is C6H5BrN4, 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.

Intermediate B (230 mg, 1.08 mmol) and the product from step 2 (396 mg, 1.30 mmol) were dissolved in 5 mL of 3:2 dioxane:toluene and degassed via a vacuum/N2 purge (3 cycles). 1 ,1′-Bis(diphenylphosphino)ferrocenepalladium(ll) chloride-dichloromethnane complex (39 mg, 0.05 mmol) was added followed by 2.2 mL of 2M aqueous Na2CO3 and the mixture was heated with stirring to 85 0C overnight. The dark green reaction mixture was cooled to room temp, filtered through a Celite pad and the pad washed well with EtOAc. The organic phase was washed with water, 2M aqueous Na2CO3, water and brine, dried over Na2SO4, filtered and concentrated. The residue was purified by lsoc Red-Sep 40, 80% – 100% EtOAc/hexanes to give 173 mg (41%) of the title compound. 1H-NMR (DMSO-cfe) .8 7.90 (s, 1 H), 7.75 (bs, 2H), 7.61, (S, 1H), 7.53 (d, 1 H), 7.28 (t, 1 H), 7.02 (d, 1 H), 6.97 (d, 1 H), 6.83 (dd, 1H) 3.45 (m, 4H), 3.16 (m, 4H), 1.43 (s, 9H); LC-MS [M+H]+ = 395.10, RT = 2.71 min.

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; BAYER PHARMACEUTICALS CORPORATION; WO2007/56170; (2007); A2;,
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. 1647-26-3, name is 1-Bromo-2-cyclohexylethane, A new synthetic method of this compound is introduced below., SDS of cas: 1647-26-3

General procedure: To a solution of the appropriatehalide (7a-c, 9a-f or 11b-h) in 2ml of DMSO NaN3is added and the solution was stirred overnight. Then, 6,CuSO4*5H2O (0.2 eq), sodium ascorbate (0.10 eq), and 2mlof distilled water are added to the solution and the solutionwas stirred overnight. The solution is diluted in water andthe mixture is extracted 3 times with EtOAc. The combinedorganic phase is washed twice with a solution of NH4Cl5Mand then twice with brine. The combined organic phaseis dried with MgSO4, to afford the crude product. Thepurification was performed as stated for each compound.

The synthetic route of 1647-26-3 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Roy, Pierre-Philipe; Faye, Diene; Blanchard, Sebastien; Cormier, Marc; Doiron, Jeremie A.; Surette, Marc E.; Touaibia, Mohamed; Journal of Chemistry; vol. 2017; (2017);,
Bromide – Wikipedia,
bromide – Wiktionary