Author: Jessica.F

Electric Literature of 90562-10-0, A common heterocyclic compound, 90562-10-0, name is 1-Bromo-4-(3-bromopropyl)benzene, molecular formula is C9H10Br2, 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 101. Synthesis of l-[3-(4-Bromo-Phenyr)-Propyll-Pyrrolidine(Intermediate 51)51[0300] To a solution of intermediate 50 (Example 100) (3.5 g, 13 mmol) in dioxane (40 mL) was added pyrrolidine (2.1 mL, 25 mmol), followed by cesium carbonate (8.2 g, 25 mmol). The mixture was stirred at room temperature for 15 h and poured into water. The mixture was extracted with ethyl acetate and the organic layer separated, washed with brine, dried over Na2SO4 and filtered. The filtrate was concentrated and the residue purified by flash chromatography on silica gel (10% MeOH/DCM to 25% MeOH and 2% TEA/DCM) to afford the title compound (1.8 g, 53%) as a pale orange oil. [0301] 1H NMR (500 MHz, DMSOd6): delta 1.60-1.65 (m, 6H), 2.35 (t, J= 13 Hz, 2H), 2.35-2.43 (m, 4H), 2.57 (t, J= 7.7 Hz, 2H), 7.16 (d, J= 8.3 Hz, 2H)3 7.44 (d, J= 8.4 Hz, 2H)

The synthetic route of 90562-10-0 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; TARGEGEN, INC.; WO2008/8234; (2008); A1;,
Bromide – Wikipedia,
bromide – Wiktionary

Reference of 90562-10-0, 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. 90562-10-0 name is 1-Bromo-4-(3-bromopropyl)benzene, 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.

Compounds 2 (40 mg, 0.14 mmol) and 7 (27.6 mg, 0.15 mmol) were dissolved in 1.5 mL of acetonitrile and then potassium carbonate (20.7 mg, 0.15 mmol) was added to the solution. After reflux for 1 h, potassium carbonate was removed by filtration. The solvent was removed in vacuo. The residue was purified by chromatography on silica gel using chloroform-methanol (40:1) as the eluent to obtain compound 9 (52 mg, 94%) as a colorless powder. 1H NMR (400 MHz, CDCl3): delta 1.10-1.32 (m, 4H), 1.65-1.85 (m, 5H), 2.07-2.25 (m, 2H), 2.35-2.55 (m, 6H), 2.34 (t, J=7.6 Hz, 2H),2.58 (t, J=7.6 Hz, 2H), 2.70-2.80 (m, 2H), 3.30-3.40 (m, 1H), 3.90-4.05 (m, 1H), 7.05 (d, J=7.8 Hz, 2H), 7.39 (d, J=7.8 Hz, 2H). HRMS (DART) m/z calcd for C19H30BrN2O (M+H)+, 381.1542; found 381.1548.

At the same time, in my other blogs, there are other synthetic methods of this type of compound, 1-Bromo-4-(3-bromopropyl)benzene, and friends who are interested can also refer to it.

Reference:
Article; Ogawa, Kazuma; Masuda, Ryohei; Mishiro, Kenji; Wang, Mengfei; Kozaka, Takashi; Shiba, Kazuhiro; Kinuya, Seigo; Odani, Akira; Bioorganic and Medicinal Chemistry; vol. 27; 10; (2019); p. 1990 – 1996;,
Bromide – Wikipedia,
bromide – Wiktionary

Synthetic Route of 35354-37-1, 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. 35354-37-1, name is 1-Bromo-5-methylhexane belongs to bromides-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below.

Example 151 (+-)-trans-3,4-Dimethyl-N-(5-methylhexyl)-4-(3-(1-methyl-1H-imidazole-4-sulfonylamino)phenyl)piperidine To a solution of (+-)-trans-3,4-dimethyl-4-(3-(1-methyl-1H-imidazole-4-sulfonylamino)phenyl)piperidine (Preparation 41, 80 mg, 0.23 mmol) in N,N-dimethylformamide (3 ml) was added sodium hydrogen carbonate (21 mg, 0.25 mmol) and 1-bromo-5-methylhexane (43 mg, 0.24 mmol). The stirred reaction mixture was heated at 100° C. for 5 h, then concentrated in vacuo at 80° C. The residue was taken up in dichloromethane and purified by silica column chromatography, eluding with ethyl acetate:isopropanol (95:5) to give the title compound as a white solid (34 mg, 33 NMR (CDCl3, selected data for the free base): 0.6 (d, 3H), 0.85 (m, 6H), 1.25 (s, 3H), 3.6 (s, 3H), 7.0-7.25 (s, 5H), 7.45 (s, 1H). MS (thermospray): M/Z [MH+] 447.3; C24H38N4O2S+H requires 447.3.

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-Bromo-5-methylhexane, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; Armer, Richard Edward; Dutton, Christopher James; Gethin, David Morris; Gibson, Stephen Paul; Smith, Julian Duncan; Tommasini, Ivan; US2003/78282; (2003); A1;,
Bromide – Wikipedia,
bromide – Wiktionary

Electric Literature of 35354-37-1, In the chemical reaction process, reaction time, type of solvent, can easily affect the result of the reaction, thereby determining the yield and properties of the reaction product. An updated downstream synthesis route of 35354-37-1 as follows.

Example 44 (+-)-4-(3-Methanesulfonylaminophenyl)-trans-3,4-dimethyl-N-(5-methylhexyl)piperidine To a stirred solution of (+-)-4-(3-methanesulfonylaminophenyl)-trans-3,4-dimethylpiperidine (Preparation 10, 25 mg, 0.088 mmol) in N,N-dimethylformamide (2 ml) was added sodium hydrogen carbonate (11 mg, 0.13 mmol) and 1-bromo-5-methylhexane (20 mg, 0.11 mmol). The reaction was heated to 90° C. for 24 h and then cooled to room temperature. The reaction mixture was diluted with water (40 ml) and extracted with diethyl ether (2*20 ml). The combined extracts were dried (MgSO4), filtered and concentrated in vacuo to give the crude product. This was purified by silica (5 g) column chromatography eluding with ethyl acetate:hexane (4:1) to give the title compound as a light brown gum (11 mg, 32percent). NMR (CDCl3, selected data for the free base): 0.75 (d, 3H), 0.8 (m, 6H), 1.2 (m, 3H), 2.55 (m, 2H), 3.0 (s, 3H), 7.0-7.4 (m, 4H). MS (thermospray): M/Z [MH+] 381.3; C21H36N2O2S+H requires 381.3.

According to the analysis of related databases, 35354-37-1, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Armer, Richard Edward; Dutton, Christopher James; Gethin, David Morris; Gibson, Stephen Paul; Smith, Julian Duncan; Tommasini, Ivan; US2003/78282; (2003); A1;,
Bromide – Wikipedia,
bromide – Wiktionary

Related Products of 105309-59-9, 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. 105309-59-9, name is Tetrakis(4-bromophenyl)methane belongs to bromides-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below.

The H4MTBC bridging ligand was prepared in two steps as shown in FIG. 11. First, the intermediate tetramethyl 4?,4??,4???,4????-methanetetrayltetrakis([1,1?-biphenyl]-4-carboxylate) (Me4MTBC) (CAS: 1208241-39-7) was synthesized using a modified procedure from the literature. Tetrakis(4-bromophenyl)methane (723 mg, 1.14 mmol, 1 equiv.), Pd(PPh3)4 (132 mg, 0.114 mmol, 0.1 equiv.), 4-(methoxycarbonyl)phenylboronic acid (1.23 g, 6.82 mmol, 6 equiv.) and CsF (3.11 g, 20.46 mmol, 18 equiv.) were charged in a 120 mL high-pressure reaction tube and pumped into an N2 glove box. To the reaction tube was added 60 mL of degassed dimethoxyethane, and the tube was capped and stirred at 85 C. for 3 days. Progress of the reaction was monitored by thin layer chromatography (TLC) (1% EtOAc/CHCl3). After cooling to room temperature, the reaction mixture was transferred to a round-bottom flask and evaporated with a rotavap. The resulting solid was dissolved with CHCl3 and filtered through celite to remove CsF and Pd nanoparticles. The filtrate was evaporated with a rotavap, then purified by flash column chromatography on silica gel using 1% EtOAc/Hexane as eluent to give white solid as pure product (572 mg, 59% yield). 1H NMR (500 MHz, CDCl3): delta 8.10 (d, 3JH=8.3 Hz, 8H), 7.68 (d, 3JHH=8.3 Hz, 8H), 7.59 (d, 3JHH=8.4 Hz, 8H), 7.44 (d, 3JHH=8.5 Hz, 8H), 3.94 (s, 12H).

The synthetic route of Tetrakis(4-bromophenyl)methane has been constantly updated, and we look forward to future research findings.

Reference:
Patent; The University of Chicago; Lin, Wenbin; Manna, Kuntal; Ji, Pengfei; (83 pag.)US2018/361370; (2018); A1;,
Bromide – Wikipedia,
bromide – Wiktionary

Related Products of 89523-51-3, In the chemical reaction process, reaction time, type of solvent, can easily affect the result of the reaction, thereby determining the yield and properties of the reaction product. An updated downstream synthesis route of 89523-51-3 as follows.

Argon atmosphere, 3-bromo-fluoranthene 12.3g, 2-chloroaniline 5.60g, tris-dibenzylideneacetone dipalladium (0) 0.732g, Tri-t-butylphosphine tetrafluoroborate dihydro 0.926g borate, -t- sodium butoxide, 7.68g, was stirred in a 400mL flask, and dehydrated toluene, heated at 80 8 hours. After cooling to room temperature (25 ), the reaction solution was extracted with toluene, and was filtered through Celite. Filtrate was concentrated, and the residue was purified by column chromatography on silica gel, 5- (2-chloro-2,3,4) benzo [c] phenanthrene was obtained a 11.32g.

According to the analysis of related databases, 89523-51-3, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Idemitsu Kosan Corporation; Kawamura, Masahiro; Mizuki, Yumiko; Ito, Hirokazu; Hayama, Tomoharu; Haketa, Tasuku; (69 pag.)KR2015/126340; (2015); A;,
Bromide – Wikipedia,
bromide – Wiktionary

Related Products of 1435-54-7, 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. 1435-54-7 name is 1,3-Dibromo-2-fluorobenzene, 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.

To a solution of 1,3-dibromo-2-fluorobenzene (1 equiv) in DMF/EtrN (1 : 1) is added Pdi PPh ; ): (3 mol %) and 4-ethynyl-3-fluorobenzonitrile (2 equiv), and the mixture is stirred for 5 minutes. Sodium ascorbate (6 mol % in DMF) and CuS04 (1 mol % in DMF) are then added, and the reaction is stirred at 80 C for 4 hours. The reaction is diluted with EtOAc and washed with saturated NH4C1 solution and brine. The organic layer is dried over anhydrous Na?.SQ4, filtered, and concentrated under reduced pressure. The crude residue is purified by column chromatography on silica gel to provide 4,4′-((2-fluoro-1,3-phenylene)bis(ethyne-2,1-diyl))bis(3-fluorobenzonitrile) .

At the same time, in my other blogs, there are other synthetic methods of this type of compound, 1,3-Dibromo-2-fluorobenzene, and friends who are interested can also refer to it.

Reference:
Patent; GEORGIA STATE UNIVERSITY RESEARCH FOUNDATION, INC.; WANG, Binghe; BOYKIN, David, W.; CHOUDHARY, Manjusha, Roy; KUMAR, Arvind; YU, Bingchen; ZHU, Mengyuan; (498 pag.)WO2019/241566; (2019); A1;,
Bromide – Wikipedia,
bromide – Wiktionary

Synthetic Route of 51776-71-7, A common heterocyclic compound, 51776-71-7, name is 1-Bromo-4-(difluoromethyl)benzene, molecular formula is C7H5BrF2, 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 stirred mixture of l-bromo-4-(difluoromethyl)benzene (0.76 g, 3.7 mmol), bis(pinacolato)diboron (1.13 g, 4.4 mmol), l,l’-bis(diphenylphosphino)ferrocene- palladium dichloride (0.31 g, 0.37 mmol), and potassium acetate (1.09 g, 11.1 mmol) in dry 1,4-dioxane (10.0 mL) was purged three times with argon and placed under vacuum three times. The mixture was heated to 90 C and monitored with LC-MS and TLC. After 21 h, the reactions were cooled to rt then filtered through Celite. The organic solvent was removed under reduced pressure, and the residue was purified on silica gel (0-10% EtOAc in hexanes) to yield a yellow liquid as 2-(4-(difluoromethyl)phenyl)-4,4,5,5-tetramethyl-l,3,2- dioxaborolane. 1H NMR (400 MHz, DMSO-d6) delta ppm 7.80 (2 H, m, J=8.0 Hz), 7.57 (2 H, m, J=8.0 Hz), 7.05 (1 H, t), 1.36 (12 H, s).

The synthetic route of 51776-71-7 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; AMGEN INC.; DRANSFIELD, Paul, John; GONZALEZ LOPEZ DE TURISO, Felix; KOHN, Todd, J.; PATTAROPONG, Vatee; SIMARD, Jillian, L.; WO2012/3283; (2012); A1;,
Bromide – Wikipedia,
bromide – Wiktionary

627526-90-3, name is 1-Bromo-3-(difluoromethyl)-5-fluorobenzene, 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. Computed Properties of C7H4BrF3

A solution of 64c (41.6 g, 0.182 mol), Pd[P(Ph)3]4(0) (15 g, 13 mmol), and zinc cyanide (12.82 g, 0.109 mol) in dry DMF (400 mL) under nitrogen was heated to 80 C. for 5.5 h. The reaction mixture was cooled to RT, the yellow solid filtered and the filtrate added to water (500 mL). The filtrate was thrice extracted with Et2O and the combined extracts washed twice with water, dried (MgSO4), filtered and evaporated at 30 C. The crude was purified by SiO2 chromatography eluting with a hexane/EtOAc gradient (100:0 to 95:5 to 90:10) to provide 26.3 g of 66 as a colorless oil which partially crystallizes

The synthetic route of 627526-90-3 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Roche Palo Alto LLC; US2005/239881; (2005); 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. 1150102-47-8, name is 6-Bromo-N1-methylbenzene-1,2-diamine belongs to bromides-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below. SDS of cas: 1150102-47-8

To compound B108 (4.60 g, crude) was added HCOOH (20 mL), the resulting mixture was stirred at 90C for 12 hours. LCMS showed the reaction worked well. 50 mL water was added to quench the reaction, neutralized with saturated NaHC( to adjusted to pH = 8-9, the resulting mixture was extracted with EtOAc ( 200 mL x 3), the combined organic phase was washed with brine (150 mL), dried over anhydrous Na2S04, filtered and concentrated under reduced pressure to give compound B109 (3.70 g, 3-step yield: 83.6%) as a brown solid.

The synthetic route of 1150102-47-8 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; QURIENT CO., LTD.; LEAD DISCOVERY CENTER GMBH; NAM, Kiyean; KIM, Jaeseung; JEON, Yeejin; YU, Donghoon; SEO, Mooyoung; PARK, Dongsik; EICKHOFF, Jan; ZISCHINSKY, Gunther; (217 pag.)WO2019/197549; (2019); A1;,
Bromide – Wikipedia,
bromide – Wiktionary