Tag: M.W=100-200

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. 2924-09-6, name is 5-Bromo-2-fluoroaniline, A new synthetic method of this compound is introduced below., Formula: C6H5BrFN

Reference Example 39 2-Fluoro-5 -mercaptoaniline To a mixture of 5-bromo-2-fluoroaniline (4.15 g), methyl 3-mercaptopropionate (2.62 g), 4,5-bis(diphenylphosphino)-9,9-dimethylxanthene (0.63 g) and N,N-diisopropylethylamine (5.64 g) in 1,4-dioxane (80 mL) was added tris(dibenzylideneacetone)-dipalladium(0) (0.3 g), and the mixture was heated at reflux under an argon atmosphere overnight. The insoluble material was removed by filtration, and the filtrate was concentrated under reduced pressure. The residue was purified by column chromatography on silica gel (eluent: n-hexane/ethyl acetate = 20/1 – 5/1 – 2/1) to give 2-fluoro-5-(2-methoxy-carbonylethylthio)aniline (4.62 g). This material was dissolved in tetrahydrofuran (120 mL). To the solution was added potassium tert-butoxide (1 mol/L tetrahydrofuran solution, 80.6 mL) at -78C, and the mixture was stirred at the same temperature for 15 minutes. To the reaction mixture was added 1 mol/L hydrochloric acid (81 mL), and the reaction mixture was allowed to warm to room temperature, and stirred for 5 minutes. The mixture was poured into ethyl acetate, and the organic layer was separated. The organic layer was washed with brine, and dried over anhydrous magnesium sulfate. The solvent was removed under reduced pressure, and the residue was purified by column chromatography on silica gel (eluent: n-hexane/ethyl acetate = 4/1) to give the title compound (1.85 g).

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; Kissei Pharmaceutical Co., Ltd.; EP2143724; (2010); A1;,
Bromide – Wikipedia,
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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. 766-81-4, name is 3-Bromophenylacetylene, This compound has unique chemical properties. The synthetic route is as follows., Product Details of 766-81-4

General procedure: Step1: A mixture of Zn (3 mmol, 196.1 mg, activated by washing with dilute HCl) MeI(6 mmol, 851.6 mg) or EtI (6 mmol, 935.8 mg), phenylacetylene (2 mmol, 204.3mg) and NMP(0.5 mL) was stirred at room temperature until Zn disappeared (~ 2 h). Step 2 CH2Cl2(5 mL) and alpha-ketoneester (0.5 mmol) (oran aldehyde ) wereadded to the mixture of step 1 and the reaction was allowed to proceed at room temperature. After stirredfor ~12 h, the reaction was shown to be complete by TLC. A saturated ammonia chloride solution (10 mL)was added and the organic phase was separated.The water phase was extracted with CH2Cl2. The combined organic phase was washed withsaturated sodium chloride solution and dried with anhydrous sodiumsulfate. After concentration and column chromatograph on silica gel eluted with petroleumether/ethyl acetate (10:1), the product was obtained.

According to the analysis of related databases, 766-81-4, the application of this compound in the production field has become more and more popular.

Reference:
Article; Zhang, Wen; Cao, Yuan; Chen, Wei; Zhao, Gang; Pu, Lin; Tetrahedron Letters; vol. 56; 46; (2015); p. 6430 – 6432;,
Bromide – Wikipedia,
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Synthetic Route of 766-46-1, These common heterocyclic compound, 766-46-1, name is 2′-Bromophenylacetylene, 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.

In an appropriate amount of organic solvent DMSO,Adding 100 mmol of the compound of the above formula (I),170 mmol of the compound of the above formula (II),5 mmol two-component composite catalyst (a mixture of 1.5 mmol PdCl 2 (cod) and 3.5 mmol ferrocene), 18 mmol of the above ligand L1130 mmol of oxidant m-chloroperoxybenzoic acid and 25 mmol of acid promoter trifluoroacetic acid,After joining,The temperature was raised to 45 C and the reaction was stirred at this temperature for 6 hours.After the reaction is over,Cool naturally to room temperature,filter,The filtrate was washed thoroughly with deionized water and then with acetic acidEster extraction 2-3 times,Combine the organic phase,And dried over anhydrous magnesium sulfate,Concentrated under reduced pressure,The residue was separated by silica gel column chromatography.An equal volume ratio of a mixture of n-pentane and acetone is used as an elution solvent.Thereby obtaining a compound of the above formula (III),The yield was 96.7%.

The synthetic route of 766-46-1 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Yancheng Geruiyin Chemical Co., Ltd.; Ding Gang; (10 pag.)CN105130769; (2018); B;,
Bromide – Wikipedia,
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Synthetic Route of 556-96-7, The chemical industry reduces the impact on the environment during synthesis 556-96-7, name is 1-Bromo-3,5-dimethylbenzene, I believe this compound will play a more active role in future production and life.

Copper [(I)] iodide (19 mg, 0.1 mmol), sodium iodide (300 mg, 2.0 mmol) and aryl bromide (1.2 mmol, if solid) were added to a screw-capped test tube with a Teflon-lined septum. The tube was evacuated and backfilled with argon (3 cycles). Dry toluene (1 mL), aryl bromide (1.2 mmol, if liquid) and N, N’-dimethylethylenediamine (0.2 mmol) were added by syringes at room temperature. The reaction was stirred to [110 C] for 24 hours. The reaction mixture was allowed to room temperature and the solvent was removed in [VACUO.] 2-Propanol (1.0 mL, bench top grade without degassing and pre-drying), ethylene glycol (111 [P1L,] bench top grade), aryl thiol (1.0 mmol) and potassium carbonate (276 mg, 2.0 mmol) were added at room temperature. The reaction was heated to 80 [C] and stirred for 18-20 hours. The reaction was allowed to reach room temperature. Ethyl acetate (approx. 5 mL) and dodecane (227 [PL,] GC standard) were added. The organic phase was analyzed by GC and GC-MS. The reaction was then filtered and concentrated. The crude product was purified by column chromatography on silica gel to afford the desired diaryl sulfide product. See Figure 6.

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-3,5-dimethylbenzene, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; MASSACHUSETTS INSTITUTE OF TECHNOLOGY; WO2004/13094; (2004); A2;,
Bromide – Wikipedia,
bromide – Wiktionary

Synthetic Route of 7745-91-7,Some common heterocyclic compound, 7745-91-7, name is 3-Bromo-4-methylaniline, molecular formula is C7H8BrN, 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: Aniline derivative was added to a vessel containing HCl 37% (0.5ml) and the mixture was stirred in ice bath at 0-5C. Then, NFSPI 10 was added to the mixture and grinded at room temperature for the times shown in Table2 to produce the related diazonium salt. The phenolate compound was added slowly to the mixture to produce the desired azo dye at 0-5C. After completion of the reaction, ethyl acetate was added to the reaction mixture and stirred thoroughly. Then, poly ionic compound 9 was filtered off and the crude azo dye was isolated by evaporation of ethyl acetate. For more purification, crude product was recrystallized from ethanol/H2O. The products were characterized by their FT-IR, 1H-NMR and 13C-NMR spectra.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 3-Bromo-4-methylaniline, its application will become more common.

Reference:
Article; Valizadeh, Hassan; Shomali, Ashkan; Ghorbani, Jalal; Noorshargh, Saeideh; Dyes and Pigments; vol. 117; (2015); p. 64 – 71;,
Bromide – Wikipedia,
bromide – Wiktionary

Synthetic Route of 53078-85-6,Some common heterocyclic compound, 53078-85-6, name is 2-Bromo-5-methylaniline, molecular formula is C7H8BrN, 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 suspension of 2-bromo-5-methylaniline (9.76 g, 52.5 mmol) in 8 mL of water was added 8.8 mL of concentrated HCl. The reaction mixture was cooled in an ice/NaCl bath (approximately -5 to -10 C). Approximately 8 g of ice was added to the reaction mixture. A solution of NaNO2 (3.60 g, 52.3 mmol) in 16.2 mL of water was added slowly over 40 minutes. The solution was then stirred for an additional 30 minutes with cooling. Separately, a solution of potassium ethyl xanthogenate (10.1 g, 63.0 mmol) in 54 mL of water was prepared and heated to 60 C. The cold solution of diazonium salt was then added slowly over 20 minutes to the solution of potassium ethyl xanthogenate. The reaction mixture was stirred for an additional 30 minutes at 60 C, and then cooled to ambient temperature. It was then poured into a saturated aqueous NaHCO3 solution and extracted three times with dichloromethane. The combined organic extracts were washed with saturated brine, dried over anhydrous MgSO4, filtered, and concentrated in vacuo. To this residue was added a solution of 1.8 M KOH/EtOH, and the reaction mixture was heated to reflux for 18 hours. The reaction mixture was then cooled to ambient temperature and concentrated in vacuo. The residue was dissolved in water and extracted with diethyl ether. The aqueous phase was then acidified with concentrated HCl and extracted three times with dichloromethane. The combined organic extracts were dried over anhydrous MgSO4, filtered, concentrated, and purified by silica gel chromatography using 0-5% ethyl acetate/hexanes as eluent to provide 8.26 g (78%) of the title Compound as a pale yellow oil. 1H NMR (500 MHz, CDCl3( ^ ggd: 2.25-2.28 (m, 3H) 3.96 (s, 1H) 6.81 (d, J=8.03 Hz, 1H) 7.18 (d, J=1.89 Hz, 1H) 7.40 (d, J=8.20 Hz, 1H).

The synthetic route of 53078-85-6 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; FMC CORPORATION; XU, Ming; DEANGELIS, Andrew Jon; LAHM, George Philip; (190 pag.)WO2020/18610; (2020); A1;,
Bromide – Wikipedia,
bromide – Wiktionary

Adding a certain compound to certain chemical reactions, such as: 1647-26-3, name is 1-Bromo-2-cyclohexylethane, 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 1647-26-3, Safety of 1-Bromo-2-cyclohexylethane

The commercially available compound 25-b (0.95 g, 5.0 mmol), triphenylphosphine (2.62 g, 10.0 mmol) and toluene(25 mL) was heated at reflux for 16 hours and then cooled to room temperature. The reaction mixture was filtered and the resulting solid was extracted with acetic acidEthyl ester, and vacuum dried to give compound 25-a (1.50 g, 66%) as a white solid.

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

Reference:
Patent; Shanghai Yingli Pharmaceutical Co., Ltd.; Xu Zusheng; Lou Yangtong; Wu Tianzhi; (87 pag.)CN106478634; (2017); 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. 202865-83-6, name is 1-Bromo-3-fluoro-5-methylbenzene, This compound has unique chemical properties. The synthetic route is as follows., Recommanded Product: 1-Bromo-3-fluoro-5-methylbenzene

Example 148A 2-Bromo-6-fluoro-4-methylbenzaldehyde 1-Bromo-3-fluoro-5-methylbenzene (5.00 g, 26.5 mmol) was dissolved in tetrahydrofuran (100 mL) and cooled to -78 C. Lithium diisopropyl amide (1.8 M in tetrahydrofuran, 16.2 mL, 29.1 mmol) was added. After stirring at -78 C. for 30 min, N,N-dimethylformamide (2.32 g, 31.7 mmol) was added. After stirring at -78 C. for an additional 15 min, acetic acid (6 mL) and water (100 mL) was added and the mixture was warmed to RT. After extraction with ethyl acetate, the organic phase was washed with 1 M hydrochloride acid solution and brine, and dried over magnesium sulfate. Concentration in vacuo afforded the title compound (5.45 g, 95% of theory). GC-MS (Method 1G): Rt=4.39 min, MS (ESIPos): m/z=217 [M+H]+

According to the analysis of related databases, 202865-83-6, the application of this compound in the production field has become more and more popular.

Reference:
Patent; BAYER PHARMA AKTIENGESELLSCHAFT; Hassfeld, Jorma; KINZEL, Tom; Koebberling, Johannes; CANCHO GRANDE, Yolanda; BEYER, Kristin; Roehrig, Susanne; Koellnberger, Maria; SPERZEL, Michael; BURKHARDT, Nils; SCHLEMMER, Karl-Heinz; STEGMANN, Christian; SCHUHMACHER, Joachim; WERNER, Matthias; ELLERMANN, Manuel; US2015/126449; (2015); A1;,
Bromide – Wikipedia,
bromide – Wiktionary

Electric Literature of 2695-48-9,Some common heterocyclic compound, 2695-48-9, name is 8-Bromo-1-octene, molecular formula is C8H15Br, 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: In a glass vial with a screw cap containing methoxybenzoin (12 mg, 0.05 mmol) in acetonitrile (2 mL) and methanol (1.5 mL), alkene (0.50 mmol), BrCH2CN (120 mg, 1.00 mmol) and sodium ascorbate (198 mg, 1.00 mmol) were added consecutively. The vial was sealed with a screw cap and left stirring under household bulb irradiation (2 x 80 W household lamps, see photos below) for 16 hours. The desired product was isolated after purification by column chromatography.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 8-Bromo-1-octene, its application will become more common.

Reference:
Article; Voutyritsa, Errika; Nikitas, Nikolaos F.; Apostolopoulou, Mary K.; Gerogiannopoulou, Anna Dimitra D.; Kokotos, Christoforos G.; Synthesis; vol. 50; 17; (2018); p. 3395 – 3401;,
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. 348-57-2, name is 1-Bromo-2,4-difluorobenzene, This compound has unique chemical properties. The synthetic route is as follows., SDS of cas: 348-57-2

A screw-cap vial equipped with a magnetic stir bar was charged with aryl halide (1 mmol), hexa-n-butylditin (0.5 mmol),palladium acetate (0.01 mmol) and tricyclohexylphosphine (0.02 mmol),followed by anhydrous cesium fluoride (1.5 mmol). The resulting mixture was manually homogenized with a magnet. A vial was transferred to a preheated oil bath (110 °C). After 24 h, the mixture was cooled, dissolved in CH2Cl2?H2O mixture (1:1), the organic phase was separated, the solvent was evaporated in vacuo and the product was isolated by flash chromatography on a silica gel by elution with hexane?CH2Cl2 mixture.

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 348-57-2.

Reference:
Article; Gribanov, Pavel S.; Golenko, Yulia D.; Topchiy, Maxim A.; Philippova, Anna N.; Kirilenko, Nikita Yu.; Krivoshchapov, Nikolai V.; Sterligov, Grigorii K.; Asachenko, Andrey F.; Bermeshev, Maxim V.; Nechaev, Mikhail S.; Mendeleev Communications; vol. 28; 3; (2018); p. 323 – 325;,
Bromide – Wikipedia,
bromide – Wiktionary