Tag: M.W=200-300

Application of 2051-99-2, 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. 2051-99-2 name is 1-Bromo-4-isobutylbenzene, 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.

General procedure: To a 50-mL two-neck round-bottom flask equipped with a cannula were added magnesium turnings (608 mg, 25 mmol), and the flask was heated at 80 C in vacuo for 1 h. A solution of the 4-isobutylphenyl bromide (426 mg, 2.0 mmol) in THF (5 mL) was added dropwise over 3 min under argon. The mixture was heated at 50 C until the reaction was initiated. Additional 4-isobutylphenyl bromide (1.71 g, 8.0 mmol) in THF (11.6 mL) was then added slowly via cannula over 15 min. The reaction mixture was heated at reflux for 3 h, after which a solution of 4-isobutylphenyl magnesium bromide 5 was obtained. To a separate 50-mL Schlenk tube was added anhydrous CoBr2 (21.9mg, 0.10mmol), and the tube was heated at 50C in vacuo for 2h. After cooling to room temperature, the cyclopropane-based bisoxazoline ligand 2 (0.12mmol) in THF (3mL) was added under argon. The resulting mixture was stirred for 1h at the same temperature, with 2-bromopropanoate 6 (1mmol) being added via syringe. The mixture solution was cooled to -80C, and the prepared Grignard reagent 5 (2.8mL, 0.5M in THF, 1.4mmol) was then added over 1h via syringe. The reaction mixture was stirred for another 6h at -80C and then quenched with saturated NH4Cl solution (5mL). The aqueous phase was extracted with diethyl ether (4×10mL). The combined organic phases were dried over anhydrous Na2SO4, and concentrated under reduced pressure. The residue was purified by silica gel chromatography (n-hexane/ethyl acetate 100:1). 4.4.8 (S)-Cyclohexylmethyl 2-(4-isobutylphenyl)propanoate 7h Colorless oil, 89% yield, 86:14 er. The enantiomeric ratio was determined by HPLC with a Daicel Chiralcel OJ-H column (0.5% 2-propanol in n-hexane, 0.5 mL/min, 220 nm, minor tr = 8.45 min (R), major tr = 9.84 min (S)). [alpha]D20 = +18.3 (c 1.1, CHCl3). 1H NMR (300 MHz, CDCl3) delta: 7.20 (d, J = 8.1 Hz, 2H), 7.08 (d, J = 8.1 Hz, 2H), 3.92-3.81 (m, 2H), 3.69 (q, J = 7.2 Hz, 1H), 2.44 (d, J = 7.2 Hz, 2H), 1.88-1.79 (m, 1H), 1.68-1.57 (m, 6H), 1.49 (d, J = 7.2 Hz, 3H), 1.25-1.06 (m, 3H), 0.89 (d, J = 6.6 Hz, 6H), 0.84-0.79 (m, 2H). 13C NMR (75 MHz, CDCl3) delta: 174.7, 140.4, 138.0, 129.2, 127.1, 69.7, 45.2, 45.0, 37.1, 30.2, 29.5, 29.46, 26.3, 25.6, 22.3, 18.3. HRMS (APCI-TOF): calcd for C20H31O2 [M+H]+ 303.2324, found 303.2329.

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

Reference:
Article; Liu, Feipeng; Bian, Qinghua; Mao, Jianyou; Gao, Zidong; Liu, Dan; Liu, Shikuo; Wang, Xueyang; Wang, Yu; Wang, Min; Zhong, Jiangchun; Tetrahedron Asymmetry; vol. 27; 14-15; (2016); p. 663 – 669;,
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. 402-43-7, name is 1-Bromo-4-(trifluoromethyl)benzene, This compound has unique chemical properties. The synthetic route is as follows., Formula: C7H4BrF3

General procedure: In a Schlenk tube, substrate (0.5 mmol), silane (0.6 mmol), base (1.5 mmol) and decane (71 mg, 0.5 mmol) as internal standard were added to 1 mL of preformed palladium nanoparticles (total amount of palladium 0.01 mmol) under argon. The reaction mixture was heated at 80 C and stirred for the indicated time (3-24 h), and then cooled down to room temperature. The organic products were extracted from glycerol with dichloromethane (5 * 3 mL). The obtained products were previously described in the literature and their identification was carried out by comparison of their GC-MS data, 1H and 13C NMR spectra with the reported data (see Table S1 in the Supporting Information).

According to the analysis of related databases, 402-43-7, the application of this compound in the production field has become more and more popular.

Reference:
Article; Reina, Antonio; Serrano-Maldonado, Alejandro; Teuma, Emmanuelle; Martin, Erika; Gomez, Montserrat; Catalysis Communications; vol. 104; (2018); p. 22 – 27;,
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. 454-79-5, name is 2-Bromo-5-(trifluoromethyl)aniline, A new synthetic method of this compound is introduced below., SDS of cas: 454-79-5

Step 7: Preparation of 2-Pyridin-2-yl-5-trifluoromethyl-phenylamine (24). A screw cap tube was charged with 2-tributyltinpyridine (1.4 eq), prepared from 2-bromopyridine and tributyltin hydride according to the procedure described in example 19-1, o-bromoaniline (200 mg, 1 eq), Pd(dba)2 (10-14 mg, 2 mol%), CuI (20-mg, 10 mol%), and PPh3 (40 mg, 15 mol%). The mixture was degassed and back-filled with argon. Dry diethyl ether (5 ml) was added, and the reaction mixture was heated at 1200C for 4h in a microwave oven. The reaction mixture was cooled to room temperature, stirred with saturated aqueous KF (3 ml) for 3h, and filtered. The solid was discarded after washing with ethyl acetate (three times). The liquid was poured into H2O and extracted with ethyl acetate. The combined organic layer was washed with H2O and brine, dried over MgSO4, and filtered and the solvent was removed in vacuo. The residue was purified by column chromatography on silica (ethyl acetate/petroleum ether as eluent) to afford the title compound as a white solid (60 mg, 38%). M+ 239.

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; TIBOTEC PHARMACEUTICALS LTD.; MEDIVIR AB; WO2008/96002; (2008); A1;,
Bromide – Wikipedia,
bromide – Wiktionary

Application of 1435-52-5, These common heterocyclic compound, 1435-52-5, name is 1,4-Dibromo-2-fluorobenzene, 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.

150ml three-necked flask, Add 0.01 mol of 2,5-dibromofluorobenzene, 0.012 mol of M2 0.02mol sodium carbonate and 10ml ethylene glycol dimethyl ether, protected by nitrogen Heat to 190 ° C and stir the reaction for 48 hours. Then cooled to room temperature and poured into a beaker. Add 50 ml of toluene and 50 ml of water and stir for 20 minutes. Filtered, the filtrate is steamed, Pass the silica gel column, Obtaining white intermediate 3a with a purity of 98.10percent, The yield was 77.5percent.

The synthetic route of 1435-52-5 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Jiangsu March Optoelectric Technology Co., Ltd.; Ye Zhonghua; Zhang Zhaochao; Li Chong; Zhang Xiaoqing; (57 pag.)CN109575057; (2019); A;,
Bromide – Wikipedia,
bromide – Wiktionary

Application of 937046-98-5, 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. 937046-98-5, name is 7-Bromopyrrolo[2,1-f][1,2,4]triazin-4-amine, This compound has unique chemical properties. The synthetic route is as follows.

To a suspension of N-methyltetrahydro-2H-pyran-4-amine (541 mg, 4.69 mmol) and (3-(bromomethyl)phenyl)boronic acid (756 mg, 3.52 mmol) in acetonitrile (8 mL) was added K2C03 (973 mg, 7.04 mmol) under anhydrous conditions. After stirring at room temperature for 10 h, the reaction mixture was concentrated, phosphoric acid,potassium salt (1.50 g, 2.35 mmol), 7-bromopyrrolo[2,1-f][1,2,4]triazin-4-amine (500 mg, 2.347 mmol), dioxane (8 mL) and water (4 mL) were added. The reaction vessel was evacuated, backfilled with N2 and then degassed by bubbling N2 with sonication. Tetrakis triphenylphosphine (271 mg, 0.235 mol) was added and the degassing process was repeated. The resulting reaction mixture was heated at 140 C in a microwave for 45mm. The reaction complex was cooled, filtered, and washed with water. The filtrate was extracted with ethyl acetate (10 mL x 3). The organic layers were combined, dried and concentrated. The crude mixture was dissolved in DMF, and purified by preparative LC Method C to obtain 7-(3 -((methyl(tetrahydro-2H-pyran-4-yl)amino)methyl)phenyl) pyrrolo[2,1-f][1,2,4]triazin-4-amine, TFA (636 mg, 60% yield). LC/MS (M+H) =338.30.

The chemical industry reduces the impact on the environment during synthesis 7-Bromopyrrolo[2,1-f][1,2,4]triazin-4-amine. I believe this compound will play a more active role in future production and life.

Reference:
Patent; BRISTOL-MYERS SQUIBB COMPANY; BHIDE, Rajeev S.; BATT, Douglas G.; CHERNEY, Robert J.; CORNELIUS, Lyndon A.M.; LIU, Qingjie; MARCOUX, David; NEELS, James; POSS, Michael A.; QIN, Lan-ying; RUAN, Zheming; SHI, Qing; SRIVASTAVA, Anurag S.; TINO, Joseph A.; WATTERSON, Scott Hunter; (532 pag.)WO2016/64957; (2016); A1;,
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. 33070-32-5, name is 5-Bromo-2,2-difluorobenzodioxole, This compound has unique chemical properties. The synthetic route is as follows., Computed Properties of C7H3BrF2O2

A solution of 5-bromo-2,2-difluoro-1 ,3-benzodioxole (2.65 mmol), 4-(4,4,5,5- tetramethyl-1 ,3,2-dioxaborolan-2-yl)aniline (3.97 mmol), tetrakis(triphenylphosphine)palladium(0) (0.08 mmol), and cesium carbonate (7.94 mmol) in Lambda/,Lambda/-dimethylformamide (8.0 ml.) and water (2.0 ml_) was heated at 100 0C for 18 h. The reaction mixture was cooled, poured into brine (60 ml_), and extracted with ethyl acetate (3 x 50 ml_). The combined organic layers were dried over magnesium sulfate and decolorizing charcoal, filtered through Celite, and concentrated in vacuo. Purification of the residue by Gilson reverse phase HPLC and neutralization of the collected fractions afforded the title product as a white solid (50%). ESMS [M+H]+: 250.2.

According to the analysis of related databases, 33070-32-5, the application of this compound in the production field has become more and more popular.

Reference:
Patent; SMITHKLINE BEECHAM CORPORATION; CYTOKINETICS; WO2006/20358; (2006); A2;,
Bromide – Wikipedia,
bromide – Wiktionary

These common heterocyclic compound, 21524-34-5, name is 2-Bromo-1,3,5-triisopropylbenzene, 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. Product Details of 21524-34-5

To a stirred tetrahydrofuran solution of bromide S12 (3.0 mmol) at -78 C was slowly added dropwise a solution of n-butyllithium (2.4M, 1.5 mL).After stirring for 30 minutes, phosphorus trichloride was added, and then the reaction mixture was warmed to room temperature and stirred for 12 hours.After the complete conversion (monitored by TLC), the prepared CuCl·LiCl complex and zinc zinc lithium benzoate complex were added to the reaction solution.The reaction was continued for 12 hours and quenched by adding water.The organic layer was separated, dried, filtered and concentrated in vacuo.The residue thus obtained was purified by silica gel column chromatography (petroleum ether: ethyl acetate ratio: 20: 1) to obtain S13 (72% yield).

The synthetic route of 2-Bromo-1,3,5-triisopropylbenzene has been constantly updated, and we look forward to future research findings.

Reference:
Patent; South University of Science and Technology of China; Liu Xinyuan; Ma Canliang; Dong Xiaoyang; (27 pag.)CN110590841; (2019); A;,
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. category: bromides-buliding-blocks

(A) To a solution of 3-bromo-5-fluorobenzaldehyde (15 g, 73.89 mmol, 1 eq) in DCM (150 ml) was addedDAST (39 ml, 295.5 mmol 4 eq) dropwise at -78C and the mixture was stirred at RT for 16 h. Aftercompletion of the reaction, the mixture was poured into ice-cold water and basified with sat. NaHCO3solution. The mixture was then extracted with DCM (3 x 200 ml), washed with water (200 ml) and brine (200 ml), dried (Na2SQ4), and concentrated in vacuum to give the crude product, which was purified by flash chromatography to afford 1 -bromo-3-(difluoromethyl)-5-fluorobenzene (10 g, 60%).

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

Reference:
Patent; GRUeNENTHAL GMBH; SCHUNK, Stefan; REICH, Melanie; JAKOB, Florian; DAMANN, Nils; HAURAND, Michael; KLESS, Achim; ROGERS, Marc; SUTTON, Kathy; WO2015/158427; (2015); A1;,
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 22385-77-9 as follows. Recommanded Product: 1-Bromo-3,5-di-tert-butylbenzene

General procedure: An oven-dried Schlenk tube with the presence of magnetic stir bar which is Teflon-coated was charged with Pd(dba)2 (11.5 mg, 0.02 mmol, 2 molpercent) and ligand L4 (8.4 mg, 0.02 mmol, 2 molpercent). The flask was evacuated and backfilled with nitrogen (3 cycles). Pre-complexation of palladium and ligand was initiated by injecting freshly distilled dry dichloromethane (2.0 mL) and Et3N (0.1 mL) into the tube. The solution was stirred and warmed with hair drier till the solvent condensed on the tube wall. The solvent was removed under vacuum. Aryl bromide (1.0 mmol), KOt-Bu (0.25 mmol), and potassium hexacyanoferrate(II) trihydrate (0.23 mmol) were charged successively to the tube followed by another 3 evacuation-nitrogen refill cycles. Water (1.0 mL) and acetonitrile (1.0 mL) were used as a solvent mixture. The tube was immersed into a preheated 50 °C oil bath for 24 hours. The reaction was quenched by cooling to ambient temperature and added with EtOAc and water. The organic supernatant was analyzed by GC. The organic layer was separated and the remained aqua medium was further extracted with EtOAc (10 mL .x. 3). The combined organic phases were concentrated under reduced pressure. The crude product was purified by flash column chromatography on silica gel (230-400 mesh). The pure fractions were collected, dried under vacuum, and followed by proton (1H) and carbon (13C) NMR characterization

According to the analysis of related databases, 22385-77-9, the application of this compound in the production field has become more and more popular.

Reference:
Article; Yeung, Pui Yee; Tsang, Chun Pui; Kwong, Fuk Yee; Tetrahedron Letters; vol. 52; 52; (2011); p. 7038 – 7041;,
Bromide – Wikipedia,
bromide – Wiktionary

Related Products of 58971-11-2,Some common heterocyclic compound, 58971-11-2, name is 3-Bromophenethylamine, molecular formula is C8H10BrN, 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 2-(3-Bromophenyl) ethylamine (7.3 g, 36 mmol) and triethylamine(15 mL, 107 mmol) in dry dichloromethane (70 mL) is added trifluoroacetic anhydride drop- wise and the reaction mixture is stirred at room temperature for 2 h. The reaction mixture is diluted with dichloromethane, washed with water and brine, dried over sodium sulfate and concentrated. The crude product is purified by column chromatography (silica gel, 60-120 mesh) using 10% ethyl acetate in petroleum ether as eluent to obtain the product as light yellow solid (7.8 g, 72%).

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

Reference:
Patent; NOVARTIS AG; WO2008/76954; (2008); A2;,
Bromide – Wikipedia,
bromide – Wiktionary