Author: Jessica.F

Application of 111721-75-6, A common heterocyclic compound, 111721-75-6, name is 2-Bromo-3-fluoroaniline, molecular formula is C6H5BrFN, 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 a 50 mL microwave tube, to a solution of 20 mL of 1 ,4-dioxane and 3 mL of water degassed with argon for 15 minutes, were successively added, 900 mg (4.73 mmol) of 2-bromo-3-fluoroaniline, 2.64 g (11.84 mmol) of 3-fluoro-4-(4,4,5,5-tetramethyl-1 ,3,2-dioxaborolan-2-yl)pyridine, 1798 mg (11.84 mmol) of cesium fluoride, 216 mg (0.237 mmol) of tris(dibenzylideneacetone)pailadium(0) and 194 mg (0.474 mmol) of S-Phos. The reaction mixture was heated under microwave at 150 C for 1 hour. The cooled reaction mixture was diluted with ethyl acetate and filtered over a pad of Celite. The organic phase was washed by brine and dried over magnesium sulfate. The organic phase was concentrated under vacuo and purified by column chromatography on silica gel (40 g cartridge – gradient n-heptane/ethyl acetate) to yield 775 mg (72%) of 2-(3-fluoropyridin-4-yl)aniline. LogP = 2.38. Mass (M+H) = 207.

The synthetic route of 111721-75-6 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; BAYER AKTIENGESELLSCHAFT; CRISTAU, Pierre; DESBORDES, Philippe; DUFOUR, Jeremy; GOURGUES, Mathieu; LAMPRECHT, Sybille; LOQUE, Dominique; MEISSNER, Ruth; NAUD, Sebastien; THOMAS, Vincent; (90 pag.)WO2020/79173; (2020); 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. 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

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

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. 53078-85-6, name is 2-Bromo-5-methylaniline, This compound has unique chemical properties. The synthetic route is as follows., SDS of cas: 53078-85-6

3-phenyl-2,2-dihydroxy-3-oxopropionic acid ethyl ester (0.05 mmol) was added to the reaction flask.2-bromo-5-methylaniline (0.05 mmol),4-phenyl-1,3-cyclohexanedione (0.05 mmol),(R)-3,3,3′,3′-tetramethylspirophosphoric acid (0.005 mmol) represented by the formula (V),Anhydrous Na2SO4 (200 mg) was poured into 1 mL of dichloromethane, and the mixture was reacted at 65 C for 16 hours. After completion of the reaction, the column was directly subjected to silica gel column chromatography, and the eluent was ethyl acetate / petroleum ether = 1:30.Corresponding optically active 1-arylindole derivative (I-7), yield 73%;

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 53078-85-6.

Reference:
Patent; Zhejiang University; Lin Xufeng; Wang Lei; Zhong Jialing; (14 pag.)CN110183373; (2019); A;,
Bromide – Wikipedia,
bromide – Wiktionary

Reference of 103273-01-4,Some common heterocyclic compound, 103273-01-4, name is 2-Bromo-4-(tert-butyl)aniline, molecular formula is C10H14BrN, 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.

2 – Bromo -4 -tert-butylaniline (2 – Bromo – 4 – tertbutylaniline) 40.0g (175.34 mmol), 4 – bromobenzoyl chloride (4 – Bromobenzoyl chloride) 38.4g (175.34 mmol) and THF 360 ml 3 hoursAfter completion of the reaction, the solvent was distilled under reduced pressure. A yellowish solid compound (intermediate (7)) 55.8g (=unitz ) was obtained by solid formation using diisopropyl ether (IPE) to give a solid compound having a yellowish 77.4% color.

The synthetic route of 103273-01-4 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Co., Ltd. Leputuo; Wu Weizhen; Han Jiazhong; Jin Huizhen; Jin Xiane; Jin Kuili; Ren Zhezhu; Xi Wenji; Gao Bingzhu; (46 pag.)CN109988119; (2019); A;,
Bromide – Wikipedia,
bromide – Wiktionary

Related Products of 583-75-5, 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. 583-75-5 name is 4-Bromo-2-methylaniline, 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.

In a 100 niL RBF, 4-bromo-2-methylaniline (3.7 g, 20 mmol) and DIPEA (6.95 mL, 40 mmol) were combined with DMF (40 mL). The reaction was cooled to 0 C in an ice bath and cyclopropanecarbonyl chloride (2.1 g, 20 mmol) was added. The mixture was stirred at 0 C for 1 h. Water and EtO Ac were added to separate the phases and the aqueous phase was extracted with EtO Ac. The organic layers were combined, dried over Na2S04, filtered, and concentrated under reduced pressure to give the title compound as a white solid (4.76 g, 94%). NMR (400 MHz, CDCl3) delta ppm 7.85-7.72 (m, 1H), 7.38-7.28 (m, 2H), 7.15-7.02 (m, 1H), 2.27 (s, 3H), 1.57-1.48 (m, 1H), 1.10 (quint, J = 3.9 Hz, 2 H), 0.92-0.79 (m, 2H); MS ESI [M + H]+ 253.9, calcd for [CnHi2BrNO + H]+ 254.0.

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

Reference:
Patent; UNIVERSITY HEALTH NETWORK; LAUFER, Radoslaw; NG, Grace; LI, Sze-Wan; PAULS, Heinz W.; LIU, Yong; PATEL, Narendra Kumar B.; WO2015/70349; (2015); A1;,
Bromide – Wikipedia,
bromide – Wiktionary

Related Products of 3972-64-3, 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. 3972-64-3, name is 1-Bromo-3-(tert-butyl)benzene belongs to bromides-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below.

A 1.6M solution of”butyllithium (0.85 mL, 1. 36 mmol) was added to a solution of dicyclohexylamine (0. 27 mL, 1.36 mmol) in toluene (5 mL). After stirring for 5 min, a mixture of cisltrans isomers of 2-methyl-cyclohexanecarboxylic acid 2-trimethylsilanyl-ethyl ester (269 mg, 1.11 mmol) was added. After stirring for 30 min, 1-bromo-3-ferf-butyl-benzene (248 mg, 1.16 mmo 1) was added followed by the simultaneous addition of tri-tert-butylphosphonium tetrafluoroborate (31 mg, 107 umol) and tris (dibenzylideneacetone) dipalladium (0)-chloroform adduct (51 mg, 49.3 umol). The solution was placed into a preheated oil bath at 60 C. After stirring for 20 h, the solution was diluted with 10percent aqueous hydrochloric acid, and extracted with diethyl ether. The combined organic extracts were dried over magnesium sulfate, filtered, and concentrated. The residue was flash chromatographed with 49: 1,24 : 1, and 23: 2 hexanes: ethyl acetate as the eluant to yield 375 mg (90percent yield) of a mixture of cisltrans isomers of 1-(3-feff-butyl-phenyl)-2-methyl-cyclohexanecarboxylic acid 2-trimethylsilanyl-ethyl ester as a yellow oil. Method [2] Retention time 3.67 min by HPLC and 3.75 min by MS (M+Na=397). Method [2] Retention time 3.77 min by HPLC and 3.85 min by MS (M+Na=397).

The synthetic route of 1-Bromo-3-(tert-butyl)benzene has been constantly updated, and we look forward to future research findings.

Reference:
Patent; ELAN PHARMACEUTICALS, INC.; WO2005/87752; (2005); 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. 399-94-0, name is 1-Bromo-2,5-difluorobenzene, A new synthetic method of this compound is introduced below., Safety of 1-Bromo-2,5-difluorobenzene

THF (25 mL) was added to Magnesium metal (2.55g, 105 mmol), and then 2-bromo-1,4-difluorobenzene (19.70g, 100mmol) was addedslowly to prepare a Grignard reagent. To separately prepared THF (10mL)solution of diethyl oxalate (15.34g, 105mmol), Grignard reagent preparedearlier was added dropwise at -40 below. After completion of the addition, it was stirred for 1 hour at thereaction temperature of 0 . saturated aqueous solution of ammonium chlorideand water (200 mL) were added to the reaction solution, and extracted with ethyl acetate (200mL ×2). The organic layer was dried over magnesium sulfate, filtered, and thesolvent was evaporatedunder reduced pressure, and by distillation under reducedpressure, colorless liquid of 2- (2,5-difluorophenyl) -2- oxo-ethyl acetate(14.82g, yield: 62%)

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; SAGAMI CHEMICAL RESEARCH INSTITUTE; KAKEN PHARMACEUTICAL COMPANY LIMITED; KOBAYASHI, OSAMU; TAKATSUNA, REIKO; NIIKURA, NAOKO; MATSUKAWA, TOMOKO; NAKAMURA, SHINJI; HIRAI, KENJI; KOCHI, SHINICHIRO; KAWANISHI, NAOKI; YAMADA, OSAMU; (75 pag.)JP2016/56157; (2016); 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. 50548-45-3, name is 1-Bromodibenzo[b,d]furan, A new synthetic method of this compound is introduced below., Application In Synthesis of 1-Bromodibenzo[b,d]furan

15.5 g (72 mmol) of the intermediate (13) obtained in [Reaction Formula 16] and 16.2 g (65.5 mmol)1-bromodibenzofuranyl group, added to a 1 L three-necked flask,Add 300 ml of toluene and 75 ml of ethanol to dissolve, and pass nitrogen for 15 minutes.An additional 98.3 ml of an aqueous solution of K2CO3 (196.5 mmol, 2 M) was added.Finally, 1.5 g of Pd(PPh3)4 (2 molpercent) was added. Warming up to 110 ° C,The reaction was completed in 12 hours. Adsorption with activated carbon, suction filtration, solvent removal, drying, recrystallization from toluene and ethanol afforded 19 g of intermediate (14), yield 86percent.

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; Nanjing Gao Guang Semiconductor Materials Co., Ltd.; Bu Gonggaofamingren; (47 pag.)CN108148037; (2018); A;,
Bromide – Wikipedia,
bromide – Wiktionary