Author: Jessica.F

Related Products of 21865-50-9,Some common heterocyclic compound, 21865-50-9, name is 6-Bromo-2,3,4,9-tetrahydro-1H-carbazole, molecular formula is C12H12BrN, 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.

Step 3. 6-Bromo-9-ethyl-2,3,4,9-tetrahydro-1H-carbazole; A 500-mL round-bottomed flask was charged with 3-bromo-6,7,8,9-tetrahydro-5H-carbazole (5 g, 20.08 mmol, 1.00 equiv) in N,N-dimethylformamide (270 mL). To this solution was added sodium hydride (1.2 g, 30.00 mmol, 1.50 equiv, 60%) in several batches at -10 C., followed by addition of iodoethane (6.26 g, 40.13 mmol, 2.00 equiv) as a solution in N,N-dimethylformamide (30 mL) drop wise -10 C. The resulting mixture was stirred at room temperature for 30 minutes. The reaction progress was monitored by TLC (EtOAc:PE=1:1). Upon completion, the reaction was then quenched by the addition of water/ice (120 mL). Then, the mixture was extracted with ethyl acetate (4×80 mL). The combined organic layers were dried over anhydrous sodium sulfate, filtered off and concentrated on a rotary evaporator. The residue was purified by a silica gel column chromatography eluted with ethyl acetate/petroleum ether (1/20) affording 3-bromo-9-ethyl-6,7,8,9-tetrahydro-5H-carbazole as brown oil (5 g, 90%).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 6-Bromo-2,3,4,9-tetrahydro-1H-carbazole, its application will become more common.

Reference:
Patent; Kalypsys, Inc; US8080566; (2011); B1;,
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. 392-83-6, name is 2-Bromobenzotrifluoride, A new synthetic method of this compound is introduced below., Recommanded Product: 392-83-6

General procedure: A test tube equipped with a magnetic stir bar was charged with an aryl halide(aryl halide, 1 mmol),CuSO4.5H2O(12.5 mg, 0.05 mmol),KOH (280 mg, 5 mmol) orCs2CO3 (1.62 g, 5 mmol), DMSO (2 mL), and water (0.2 mL; water was not used in case of using Cs2CO3 as base).After flushing with argon, 1,2-ethanedithiol (0.18 mL, 2 mmol) was added.The mixture was heated in a preheated oil bath for 20 hours90 C or 110 C bath which is pre-heated with agitation.After cooling to ambient temperature, the reaction mixture was distributed in aqueous HCl (5%) and ethyl acetate. The organic layer was washed with water and brine, dried over anhydrous MgSO4 and concentrated in vacuo. The crude product was purified by column chromatography (EtOAc / n-Hexane) to give the aryl thiol (see Table 2 below).

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; SUNGSHIN WOMEN`S UNIVERSITY INDUSTRY-ACADEMIC COOPERATION FOUNDATION; CHAE, Junghyun; Liu, Ya jun; KIM, Ji hye; (18 pag.)KR2017/76524; (2017); 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. 41825-73-4, name is 2-Bromo-4,6-dimethylaniline, A new synthetic method of this compound is introduced below., SDS of cas: 41825-73-4

N-(2-Bromo-4,6-dimethylphenyl)(4,5-dimethyl-6H-cyclopenta[b]thien-6-yl)dimethylsilanamine Under an argon atmosphere, to a solution of 14.8 g (74.2 mmol) of 2-bromo-4,6-dimethylaniline in 200 ml of THF, 29.7 ml of 2.5 M (74.2 mmol) nBuLi in hexanes was added at -80 C. This mixture was warmed for ca. 1 hour to ambient temperature. Then, the resulting solution was added dropwise over ca. 1 hour, while vigorously stirring, to a solution of 18.0 g (74.2 mmol) of chloro(4,5-dimethyl-6H-cyclopenta[b]thien-6-yl)dimethylsilane in 100 ml of THF. The resulting mixture was stirred overnight at ambient temperature, and then, evaporated to dryness. To the residue, 150 ml of toluene was added. This mixture was filtered through a glass frit (G4). The filtrate was evaporated to dryness. Fractional distillation gave a yellow liquid, bp 168-172 C./0.2 mm Hg. The product crystallizes slowly at ambient temperature. Yield 16.5 g (55%). Anal. calc. for C19H24BrNSSi: C, 56.14; H, 5.95. Found: C, 56.28; H, 6.09. 1H NMR (CDCl3): delta 7.20 (d, J=4.9 Hz, 1H, 3-H in cyclopenta[b]thiophene), 7.18 (m, 1H, 3-H in phenyl), 6.97 (d, J=4.9 Hz, 1H, 2-H in cyclopenta[b]thiophene), 6.85 (m, 1H, 5-H in phenyl), 3.59 (br.s, 1H, 6-H in cyclopenta[b]thiophene, 2.92 (br.s, 1H, NH), 2.21 (s, 3H, 4-Me in phenyl), 2.19 (s, 3H, 6-Me in phenyl), 2.13 (s, 3H, 4-Me in cyclopenta[b]thiophene), 2.10 (s, 3H, 5-Me in cyclopenta[b]thiophene), 0.14 (s, 3H, SiMeMe’), 0.06 (s, 3H, SiMeMe’). 13C NMR (CDCl3): delta 152.2, 140.7, 140.0, 139.2, 132.6, 132.4, 131.2, 131.1, 130.0, 126.2, 119.9, 118.0, 49.2, 20.8, 20.6, 15.4, 12.1, -1.8, -2.1.N-(2-Bromo-4,6-dimethylphenyl)(4,5-dimethyl-6H-cyclopenta[b]thien-6-yl)dimethylsilanamine Under and argon atmosphere, to a solution of 14.8 g (74.2 mmol) of 2-bromo-4,6-dimethylaniline in 200 ml of THF, 29.7 ml of 2.5 M (74.2 mmol) nBuLi in hexanes was added at -80 C. This mixture was warmed for ca. 1 hour to ambient temperature. Then, the resulting solution was added dropwise for ca. 1 hour while vigorously stirring to a solution of 18.0 g (74.2 mmol) of chloro(4,5-dimethyl-6H-cyclopenta[b]thien-6-yl)dimethylsilane in 100 ml of THF. The resulting mixture was stirred overnight at ambient temperature, then, evaporated to dryness. To the residue, 150 ml of toluene was added. This mixture was filtered through a glass frit (G4). The filtrate was evaporated to dryness. Fractional distillation gave a yellow liquid, bp 168-172 C./0.2 mm Hg. The product crystallizes slowly at ambient temperature. Yield 16.5 g (55%). Anal. calc. for C19H24BrNSSi: C, 56.14; H, 5.95. Found: C, 56.28; H, 6.09. 1H NMR (CDCl3): delta 7.20 (d, J=4.9 Hz, 1H, 3-H in cyclopenta[b]thiophene), 7.18 (m, 1H, 3-H in phenyl), 6.97 (d, J=4.9 Hz, 1H, 2-H in cyclopenta[b]thiophene), 6.85 (m, 1H, 5-H in phenyl), 3.59 (br.s, 1H, 6-H in cyclopenta[b]thiophene, 2.92 (br.s, 1H, NH), 2.21 (s, 3H, 4-Me in phenyl), 2.19 (s, 3H, 6-Me in phenyl), 2.13 (s, 3H, 4-Me in cyclopenta[b]thiophene), 2.10 (s, 3H, 5-Me in cyclopenta[b]thiophene), 0.14 (s, 3H, SiMeMe’), 0.06 (s, 3H, SiMeMe’). 13C NMR (CDCl3): delta 152.2, 140.7, 140.0, 139.2, 132.6, 132.4, 131.2, 131.1, 130.0, 126.2, 119.9, 118.0, 49.2, 20.8, 20.6, 15.4, 12.1, -1.8, -2.1.

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; Voskoboynikov, Alexander Z.; Ryabov, Alexey N.; Nikulin, Mikhail V.; Lygin, Alexander V.; Uborsky, Dmitry V.; Coker, Catalina L.; Canich, Jo Ann M.; US2007/135623; (2007); A1;,
Bromide – Wikipedia,
bromide – Wiktionary

320-29-6, name is 4-Bromo-1,2-bis(trifluoromethyl)benzene, 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. category: bromides-buliding-blocks

Sodium Hydride (60% oil suspension, 5 mmol, 200 mg) is triturated with hexane and suspended in N,N-dimethylformamide (4 mL). 1,2,3,9-Tetrahydro-carbazol-4-one (2.5 mmol, 462 mg) is added to the water-cooled suspension. After 5 minutes, 5-bromo-2-trifluorobenzotrifluoride (5 mmol, 0.71 g) is added. The reaction is stirred at 85 degrees Celsius for 3.5 h. The reaction mixture is allowed to cool and is extracted into ethyl acetate (200 mL) and is washed with water (50 mL). The organic phase is dried over magnesium sulfate. Filtration, followed by concentration, and silica gel chromatography affords the desired 9-(4-Bromo-2-trifluoromethyl-phenyl)-1,2,3,9-tetrahydro-carbazol-4-one as a brown foam (0.74 g, 73%).

The synthetic route of 320-29-6 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Serenex, Inc.; US2007/185184; (2007); 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. 69902-83-6, name is 1-Bromo-2-methyl-3-(trifluoromethyl)benzene, A new synthetic method of this compound is introduced below., Formula: C8H6BrF3

Step 1 : A mixture of 1-bromo-2-methyl-3-(trifluoromethyl)benzene (100 mu, 0.64 mmol), 4,4,5,5-tetramethyl-2-(tetramethyl-1 ,3,2-dioxaborolan-2-yl)-1 ,3,2- dioxaborolane (327 mg, 1.29 mmol), PdCI2dppf DCM (26 mg, 0.030 mmol) and potassium acetate (158 mg, 1.61 mmol) in 1 ,4-dioxane (5 mL) was heated in a sealed tube at 80C overnight. The mixture was run through a plug of silica (EtOAc), concentrated and purified by preparative HPLC to give 4,4,5,5- tetramethyl-2-[2-methyl-3-(trifluoromethyl)phenyl]-1 ,3,2-dioxaborolane.

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; THOMAS HELLEDAYS STIFTELSE FOeR MEDICINSK FORSKNING; SCOBIE, Martin; WALLNER, Olov; KOOLMEISTER, Tobias; VALLIN, Karl Sven Axel; HENRIKSSON, Carl Martin; HOMAN, Evert; HELLEDAY, Thomas; JACQUES, Sylvain; DESROSES, Matthieu; JACQUES-CORDONNIER, Marie-Caroline; FISKESUND, Roland Julius Yu; (359 pag.)WO2015/187089; (2015); A1;,
Bromide – Wikipedia,
bromide – Wiktionary

Synthetic Route of 5153-40-2, 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. 5153-40-2 name is 1-Bromo-2,3,4,5,6-pentamethylbenzene, 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.

The synthesis of salicylaldimine 13 was accomplished in five steps (FIG. 21). Negishi cross-coupling of 1 and pentamethylbromobenzene[Ref 54] afforded biphenyl species 9. Subsequent steps are similar to the synthesis of ligands 7-s and 7-a. Bromination, followed by lithium-halogen exchange and DMF treatment installed the formyl moiety to give 11. Deprotection of the ether group and condensation with 2,6-diisopropyl aniline provided 13 in 14% overall yield.

At the same time, in my other blogs, there are other synthetic methods of this type of compound, 1-Bromo-2,3,4,5,6-pentamethylbenzene, and friends who are interested can also refer to it.

Reference:
Patent; RADLAUER, Madalyn; WIENSCH, Joshua D.; BUCKLEY, Aya K.; AGAPIE, Theodor; US2013/66029; (2013); A1;,
Bromide – Wikipedia,
bromide – Wiktionary

Synthetic Route of 30432-16-7, These common heterocyclic compound, 30432-16-7, name is 1,4-Dibromo-2,3-bis(bromomethyl)but-2-ene, 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: Alkyl 4-hydroxy benzoate 2a,b (10 mmol) and potassium hydroxide (0.56 g, 10 mmol) were dissolved in absolute ethanol. 1,1,2,2-tetrayl-tetramethylene-tetrabromide (1) (1.00 g, 2.5 mmol) was then added into this solution. The reaction mixture was refluxed for 6 h. The mixture was cooled and filtrated. The white precipitate was filtered off and washed with H2O and crystallized from the appropriate solvent.

The synthetic route of 30432-16-7 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Er, Mustafa; De?irmencio?lu, Ismail; Tahtaci, Hakan; Spectrochimica Acta Part A: Molecular and Biomolecular Spectroscopy; vol. 139; 1; (2015); p. 68 – 74;,
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. 21865-50-9, name is 6-Bromo-2,3,4,9-tetrahydro-1H-carbazole, A new synthetic method of this compound is introduced below., Recommanded Product: 21865-50-9

To a suspension of 39 (0.75 g, 3.0 mmol) in acetic acid (3 ml) is added acetyl chloride (0.21 ml, 3.0 mmol). The mixture is heated to reflux, resulting in a clear solution. After 2 hours, the reaction solution is cooled to room temperature (rt). A solid is precipitated out. The solid 48 is filtered and washed with hexanes (2 x), 0.24 g, 27%

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; PTC THERAPEUTICS, INC.; WO2006/58088; (2006); 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. 6698-13-1, name is 4-Bromo-1,3-benzodioxole, A new synthetic method of this compound is introduced below., Quality Control of 4-Bromo-1,3-benzodioxole

The compound 4-bromobenzo[d][1,3]dioxole (5g, 24.873mmol)And sublimation sulfur (0.848g, 26.2mmol) was added to the two-necked flask, under the protection of nitrogen, was added tetrahydrofuran (100mL), cooled to -70 and stirred for 30 minutes,Slowly add hexane solution of tert-butyllithium (38mL, 49mmol, 1.3mol/L),After the dropwise addition, the reaction was continued at this temperature for 2 hours,Saturated ammonium chloride solution (100 mL) was added dropwise to quench the reaction, ethyl acetate (200 mL) was added for extraction, liquid separation, the organic phase was washed with 2N sodium hydroxide solution (20 mL), and the aqueous phases were combined,After adjusting the pH of the aqueous phase to about 4-5 with 4N hydrochloric acid, extract the aqueous phase with ethyl acetate (100 mL×2),The organic phases were combined, and the organic phase was washed with saturated sodium chloride solution (100 mL), dried over anhydrous sodium sulfate, and filtered.The filtrate was concentrated under reduced pressure to give the title compound as a yellow oil (3.12g, 81.4%).

The synthetic route of 6698-13-1 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Guangdong Dongyangguang Pharmaceutical Co., Ltd.; Luo Huichao; Ren Qingyun; Yin Junjun; Wu Chunlin; Fan Yuxin; Mo Yufeng; Zhang Yingjun; (102 pag.)CN111057074; (2020); A;,
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. 1037138-94-5, name is 2-Bromo-4-fluoro-N-methylaniline, This compound has unique chemical properties. The synthetic route is as follows., Quality Control of 2-Bromo-4-fluoro-N-methylaniline

A mixture of 2-bromo-4-fluoro-N-methylaniline (2 g, 9.8 mmol), 4,4,4′,4′,5,5,5′,5′-octamethyl-2,2′-bi-1,3,2-dioxaborolane (2.99 g, 11.76 mmol), 1,1′-bis(diphenylphosphino)ferrocenedichloro palladium(II) dichloromethane complex (359 mg, 0.490 mmol) and potassium acetate (2.89 g, 29.4 mmol) in 1,2-dimethoxyethane (60 mL) was purged with nitrogen and heated at 80 C. overnight. After cooling, heptane (100 mL) was added and the mixture was filtered through diatomaceous earth and washed with 3:1 heptane/ethyl acetate. The filtrate was concentrated and the residue was purified by flash chromatography on silica gel (Teledyne CombiFlash Rf, 5-30% ethyl acetate in heptane) to provide the title compound, which was contaminated by corresponding boronic acid. MS (DCI/NH3) m/z 252 (M+H)+.

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 1037138-94-5.

Reference:
Patent; ABBVIE INC.; Frey, Robin; Gong, Jianchun; JI, Zhiqin; Lai, Chunqiu; Penning, Thomas; Song, Xiaohong; Souers, Andrew; Tong, Yunsong; Zhu, Gui-Dong; US2015/218165; (2015); A1;,
Bromide – Wikipedia,
bromide – Wiktionary