Month: July 2021

These common heterocyclic compound, 21120-91-2, name is 7-Bromobicyclo[4.2.0]octa-1,3,5-triene, 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: C8H7Br

To a stirred solution of mercury(II) oxide (591.3 mg, 2.73 mmol) and 35 % aqueous tetrafluoroboric acid (TFBA) (999.4 mg, 5.46 mmol) in 1,4-dioxane (10.9 mL), 1- bromobenzocyclobutene (1.0 g, 5.46 mmol) was added. The reaction stirred at room temperature for 2 h and was then treated successively with NaHCO3 and 3N KOH until the solution remained basic. The precipitated mercury(II) oxide was filtered off and the filtrate extracted with CH2Cl2 (3 x 300 mL), dried with anhydrous Na2SO4, filtered, and concentrated to yield white crystals that were purified via column chromatography using a 3:2 Hexanes:EtOAc solvent system.

The synthetic route of 7-Bromobicyclo[4.2.0]octa-1,3,5-triene has been constantly updated, and we look forward to future research findings.

Reference:
Patent; VANDERBILT UNIVERSITY; WO2008/24435; (2008); 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. 75024-22-5, name is 1,4-Dibromo-2,3-dimethylbenzene, A new synthetic method of this compound is introduced below., Computed Properties of C8H8Br2

General procedure (a): A solution of 1,2-dimethylaryle 2b-e,h (10 mmol) and finely pulverised N-bromosuccinimide (NBS 3.68 g, 21 mmol, 2.1 equiv) in CCl4 (40-80 mL) was irradiated with HPK125 mercury lamp for 1-2 h with good stirring (tlc or 1H NMR monitoring). The reaction mixture was diluted with CH2Cl2, washed with H2O or 2 N aqueous NH4Cl solution and dried over MgSO4. The solvent was evaporated to give quantitatively 5b-e,h which was used without further purification.

The synthetic route of 75024-22-5 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Maiereanu, Carmen; Schmitt, Celine; Schifano-Faux, Nadge; Le Nouen, Didier; Defoin, Albert; Tarnus, Celine; Bioorganic and Medicinal Chemistry; vol. 19; 18; (2011); p. 5716 – 5733;,
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. 7766-50-9, name is 11-Bromo-1-undecene, A new synthetic method of this compound is introduced below., Computed Properties of C11H21Br

[0129] 86 mmol of 1 1 -bromo1 -undecene and 91 mmol of triethoxy silane were added to a single neck RBF attached with an attached reflux condenser. Then 1.0 mL Karstedt’s catalyst (2 Wt. % solution in toluene, 0.1 mmol)) was added via syringe and flask was in the oil bath between 70 C for 2h. 1H NMR of the crude mixture showed a complete consumption of chain end olefin groups, however, a close examination of the spectrum showed presence of -15-20% olefin rearrangement products. Separation of (1 1 – bromoundecyl) triethoxysilane from rearrangement olefin and excess triethoxy silane was achieved by fractional distillation under high vacuum (Yield 67%).

The synthetic route of 7766-50-9 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; MERCK PATENT GMBH; BOBADE, Sachin; POLISHCHUK, Orest; PADMANABAN, Munirathna; BASKARAN, Durairaj; (65 pag.)WO2019/81450; (2019); A1;,
Bromide – Wikipedia,
bromide – Wiktionary

Related Products of 67567-26-4, 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. 67567-26-4 name is 4-Bromo-2,6-difluoroaniline, 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.

CuCl2 (0.77 g, 5.77 mmol) was dissolved in 200 mL of water. SOCl2 (29 mL, 0.40 mol) was added thereto at0C, and the mixture was stirred at room temperature for 18 hours. 4-bromo-2,6-difluoroaniline (20 g, 0.096 mol) wasdissolved in 240 mL of HCl and 900 mL of water, and the solution in which NaNO2 (7 g, 0.10 mol) was dissolved in 200mL of water was added thereto at 0C. The above thionyl chloride solution was added thereto, and the reaction wascarried out at room temperature for 1 hour to obtain the title compound (24 g, 85 %) in a solid form.

At the same time, in my other blogs, there are other synthetic methods of this type of compound, 4-Bromo-2,6-difluoroaniline, and friends who are interested can also refer to it.

Reference:
Patent; LG Chem, Ltd.; KIM, Young Kwan; PARK, Sang Yun; JOO, Hyun Woo; CHOI, Eun Sil; PAEK, Seung Yup; KANG, Seung Wan; KIM, Byung Gyu; LEE, Chang Seok; KIM, Sung Wook; LEE, Sang Dae; (369 pag.)EP3239143; (2017); A2;,
Bromide – Wikipedia,
bromide – Wiktionary

Electric Literature of 1435-52-5, 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 1435-52-5 as follows.

In an oven-dried 100 mL round bottom flask boronic acid 3(1.00 g, 1.0 eq.) was added, followed by dibromobenzene 2 (3.60 g, 2.0 eq) and palladium reagent (150 mg) were dissolved in dioxane to give a yellow solution. Sodium bicarbonate aqueous solution (2 M, 14 mL) was added causing a beige suspension to form. The suspension was heated at 80 0C for 20 h. The reaction was evaporated to dryness and the residue partitioned between EtOAc (75 mL) and water (25 mL). The layers were separated and the organic layer washed with brine, dried over magnesium sulfate, filtered and evaporated to a yellow oil. The oil was chromatographed with hexanes to yield 1.07 g (57percent yield) of 4 as a white solid and 528 mg (30percent yield) of 5 as a white solid.

According to the analysis of related databases, 1435-52-5, the application of this compound in the production field has become more and more popular.

Reference:
Patent; INFINITY DISCOVERY, INC.; WO2008/63300; (2008); A2;,
Bromide – Wikipedia,
bromide – Wiktionary

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 82842-52-2 as follows. Quality Control of 3-Bromo-2,4,6-trimethylaniline

EXAMPLE 207 ‘N-(2,2′,4,6,6′-Pentamethyl-1,1’-biphenyl-3-yl)-3-[(phenylsulfonyl)amino]thiophene-2-carboxamide Step One: To a solution of 3-bromo-2,4,6-trimethylaniline (1.07 g, 5.0 mmol) and 2,6-dimethylphenyl boronic acid (1.5 g, 10 mmol) in toluene (10 mL) was added potassium phosphate, tribasic (3.2 g, 15 mmol) and the resulting mixture was deoxygenated by passing a stream of nitrogen for approximately 10 minutes. 2-Dicyclohexylphosphino-2,6-dimethoxy-1,1’biphenyl (0.164 g, 0.4 mmol) and tris(dibenzylidineacetone)dipalladium(0) (92 mg, 0.1 mmol) were added together in one portion, and nitrogen bubbling continued for approximately 2 minutes. The mixture was then heated in an oil bath at 110 C. under nitrogen overnight. The mixture was cooled, concentrated and passed through a pad of course silica gel. The resulting residue was purified on silica using 14:1 to hexanes to ethyl acetate. The residue from this operation was then vacuum distilled (Kugelrohr, 100 C., approximately 1 mtorr) to give the desired biphenyl (155 mg).

According to the analysis of related databases, 82842-52-2, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Wu, Chengde; Anderson, C. Eric; Bui, Huong; Gao, Daxin; Kassir, Jamal; Li, Wen; Wang, Junmei; Biediger, Ronald; Chen, Jie; Market, Robert V.; US2005/49286; (2005); A1;,
Bromide – Wikipedia,
bromide – Wiktionary

3814-30-0, name is (Bromomethyl)cyclopentane, 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. Application In Synthesis of (Bromomethyl)cyclopentane

General procedure: Potassium carbonate (791 mg, 5.7 mmol) was added to a solution of 3-iodoindazole (700 mg, 2.9 mmol) and 2-chloroethyl methyl ether (406 mg, 4.3 mmol) in ACN (20 mL) at rt. The reaction was heated to reflux overnight, and then was filtered and concentrated. The residue was purified by silica gel chromatography (15%-50% EtOAc/hexanes) to give 530 mg (63%) of the title compound as a light yellow oil. The title compounds were prepared from 5-fluoro-3-iodo-indazole and (bromomethyl)cyclopentane according to the procedure for Preparation 10A. [0365] 1-(cyclopentylmethyl)-5-fluoro-3-iodo-1H-indazole (72%) was isolated as the major isomer eluting first. 1H NMR (400 MHz, CDCl3): delta 1.25-1.32 (2H, m), 1.50-1.65 (6H, m), 2.48-2.56 (1H, m), 4.27 (2H, d, J=7.5 Hz), 7.09 (1H, dd, J=8.3, 2.3 Hz), 7.18 (1H, td, J=8.9, 2.4 Hz), 7.32 (1H, dd, J=9.1, 4.0 Hz). [M+H] calc’d for C13H14FIN2, 345. found 345. [0366] 2-(cyclopentylmethyl)-5-fluoro-3-iodo-2H-indazole (18%) was isolated as the minor isomer eluting second. 1H NMR (400 MHz, CDCl3): delta 1.33-1.42 (2H, m), 1.56-1.73 (6H, m), 2.62-2.70 (1H, m), 4.41 (2H, d, J=7.6 Hz), 7.00 (1H, dd, J=8.8, 2.4 Hz), 7.09 (1H, td, J=9.2, 2.4 Hz), 7.65 (1H, dd, J=9.3, 4.5 Hz). [M+H] calc’d for C13H14FIN2, 345. found 345.

The synthetic route of 3814-30-0 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Quanticel Pharmaceuticals, Inc.; Kanouni, Toufike; Stafford, Jeffrey Alan; Veal, James Marvin; Wallace, Michael Brennen; US2014/171432; (2014); A1;,
Bromide – Wikipedia,
bromide – Wiktionary

Related Products of 138526-69-9, A common heterocyclic compound, 138526-69-9, name is 1-Bromo-3,4,5-trifluorobenzene, molecular formula is C6H2BrF3, 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 100 g of this 2-iodo-7-propyl-9,10-dihydrophenanthrene in 300 mL of THF was added 3.3 g of tetrakis(triphenylphosphine)palladium (0) and the mixture was stirred at room temperature. This mixture was then reacted with a Grignard reagent prepared from 79 g of 3,4,5-trifluorobromobenzene and 9.1 g of magnesium. Following stirring for 2 hours at room temperature, the mixture was allowed to cool to room temperature, water was added, the product was extracted into toluene, and the organic layer was washed sequentially with water and a saturated aqueous solution of sodium chloride before being dried over anhydrous sodium sulfate. The crude product obtained by removal of the solvent by evaporation was purified by silica gel columnchromatography (hexane) and then recrystallized 3 times from ethanol to yield 45 g of white crystals of 2-propyl-7-(3,4,5-trifluorophenyl)-9,10-dihydrophenanthrene. Measurement of the phase transition temperature revealed a transition from the crystalline phase to an isotropic liquid phase at 68C under rising temperature conditions. NMR: delta = 0.99 (t, J=7Hz, 3H), delta = 1.65 (m, 2H), delta = 2.52 (t, J=7Hz, 2H), delta = 2.88 (s, 4H), delta = 6.9 to 7.6 (m, 8H), MS: m/e = 352 (M+)

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; DAINIPPON INK AND CHEMICALS, INC.; EP1201632; (2002); A1;,
Bromide – Wikipedia,
bromide – Wiktionary

64248-56-2, name is 2-Bromo-1,3-difluorobenzene, 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. name: 2-Bromo-1,3-difluorobenzene

Preparation of 2-bromo-1,3-difluoro-4-nitrobenzene [(35), G= NO2; L’ = Br; R3,R6 = F; R4,R5 = H]; To a stirred, ice-cooled, solution of 1,3-difluoro-2-bromobenzene (1.74 g, 9.0 mmol) in 96% sulphuric acid (2 mL), a mixture of 96% sulphuric acid (0.6 mL) and fuming nitric acid (0.6 mL) was slowly added, keeping the temperature below 55 0C. After addition, the reaction mixture was stirred at room temperature for 2 h, then poured onto ice. The precipitate was filtered, washed with water and dried. The title compound was obtained as a yellowish solid (1.7 g, 80%).HPLC (254 nm): Rt: 6.26 min. 1H-NMR (401 MHz, DMSO-d6) delta = 8.1 (m, 1 H) 7.1 (m, 1 H).

The synthetic route of 64248-56-2 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; NERVIANO MEDICAL SCIENCES S.R.L.; PULICI, Maurizio; ZUCCOTTO, Fabio; BADARI, Alessandra; NUVOLONI, Stefano; CERVI, Giovanni; TRAQUANDI, Gabriella; BIONDARO, Sonia; TRIFIRO’, Paolo; MARCHIONNI, Chiara; MODUGNO, Michele; WO2010/10154; (2010); A1;,
Bromide – Wikipedia,
bromide – Wiktionary

Adding a certain compound to certain chemical reactions, such as: 328-70-1, name is 1-Bromo-3,5-bis(trifluoromethyl)benzene, belongs to bromides-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 328-70-1, Application In Synthesis of 1-Bromo-3,5-bis(trifluoromethyl)benzene

A 250 ml round-bottom flask was charged with magnesium (turnings; 2.18 g; 89.5 mmol), and argonated. Then, Et2O (60 ml), I2 (one crystal) were added, and a solution of 1-bromo-3,5-bis(trifluoromethyl)benzene (26.67 g; 91.0 mmol) in Et2O (60 ml) was added portionwise over 45 min with stirring. After 2 h the mixture was cooled with ice-water bath and AsCl3 (2.2ml; 26.1 mmol) was added dropwise, that caused formation of crystalline precipitate. Stirring was continued at RT for 16 h, and aqueous NH4Cl (100 ml; 10%) was added. The resulted mixture was extracted with ethyl acetate (3 100 ml), and combined organic phases were washed with brine (100 ml), and dried over MgSO4. The mixture was filtered, evaporated, and residue grey-brownish solid was crystallized from n-hexane (dissolved in boiling solvent and slowly cooled to ca. 0 C; 30 ml) to obtain 8d (17.99 g; 25.18 mmol; 97%) as white solid.

If you are interested in these compounds, you can also browse my other articles.Thank you for taking the time to read this article. I hope you enjoyed it.

Reference:
Article; Grudzie?, Krzysztof; Basak, Tymoteusz; Barbasiewicz, Micha?; Wojciechowski, Tomasz M.; Fedory?ski, Micha?; Journal of Fluorine Chemistry; vol. 197; (2017); p. 106 – 110;,
Bromide – Wikipedia,
bromide – Wiktionary