Tag: M.W=200-300

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., Application In Synthesis of 1,4-Dibromo-2,3-dimethylbenzene

100 g (380 mmol) of 1,4-dibromo-2,3-dimethylbenzene are dissolved in 1500 ml of dry diethyl ether, 420 ml (840 mmol) of a 2 M solution of n-butyllithium in cyclohexane are added dropwise at -70 C., after 1 h 130 ml of trimethyl borate (1140 mmol) are added dropwise, the mixture is allowed to come to RT over the course of 1 h, the solvent is removed, 90 g (76 mmol) of pinacol and 1000 ml of toluene are added, the mixture is heated at the boil for 2 h, the solvent is removed again, and the residue, which is homogeneous according to 1H-NMR, is employed in the subsequent reaction without further purification.

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; Merck Patent GmbH; US2011/92701; (2011); A1;,
Bromide – Wikipedia,
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Synthetic Route of 203302-95-8, These common heterocyclic compound, 203302-95-8, name is 4-Bromo-3,5-difluoroaniline, 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.

mixture of 4-bromo-3,5-difluroaniline (400 mg, 1.923 mmol) and NCS (257 mg, 1.923 mmol) in DMF (3.8 mL) was stirred at 60C for 90 min. It was diluted with diethyl ether (40 mL), washed with water (20 mL), and brine (20 mL). The organic layer was dried over magnesium sulfate, filtered and the solvent was evaporated under reduced pressure. The residue was purified by flash column chromatography (eluting with EtOAc/hexane = 50%) to give the title compound. MS (ES+) m/z: 242, 244 (M+H).

Statistics shows that 4-Bromo-3,5-difluoroaniline is playing an increasingly important role. we look forward to future research findings about 203302-95-8.

Reference:
Patent; MERCK SHARP & DOHME CORP.; XU, Jiayi; ALI, Amjad; ZHOU, Wei; GAO, Ying-Duo; EDMONDSON, Scott, D.; MERTZ, Eric; NEELAMKAVIL, Santhosh, F.; LIU, Weiguo; SUN, Wanying; SHEN, Dong-Ming; HARPER, Bart; ZHU, Cheng; BARA, Thomas; LIM, Yeon-Hee; YANG, Meng; (227 pag.)WO2017/74832; (2017); A1;,
Bromide – Wikipedia,
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Adding a certain compound to certain chemical reactions, such as: 16518-62-0, name is 3-Bromo-N,N-dimethylaniline, 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 16518-62-0, Safety of 3-Bromo-N,N-dimethylaniline

To a solution of compoundN,N dimethyl-3-bromo aniline (10.0 g, 50.0 mmol) in AcOH (250 mL) was added 12.16 mL of 37% formaldehyde aqueous solution (4.5 g, 150.0 mmol), and the mixture was stirred at 60 C for 115 mm. After cooling to room temperature, a portion of acetic acid was removed by vacuum. Then, the reaction mixture was neutralized with saturated NaHCO3 aq. and NaOH aq., and extracted with CH2C12. The organic layer waswashed with brine, dried over Na2SO4 and evaporated to dryness. The residue was purified by flash chromatography (silica gel) to give pure 4,4?-methylenebis(3-bromo-N,N- dimethylaniline) (5.24 g, 12.7 mmol, 51% yield).

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, 3-Bromo-N,N-dimethylaniline, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; VISEN MEDICAL, INC.; GROVES, Kevin; BUFF, Ryan; WO2014/144793; (2014); A1;,
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Electric Literature of 40161-54-4, A common heterocyclic compound, 40161-54-4, name is 1-Bromo-2-fluoro-4-(trifluoromethyl)benzene, molecular formula is C7H3BrF4, 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.

EXAMPLE 3 Ex 3a N-[2′-fluoro-4′-(trifluoromethyl)-4-biphenylyl]methanesulfonamide A solution of 1-bromo-2-fluoro-4-(trifluoromethyl)benzene (0.17 mmol), N-[4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl]methanesulfonamide (0.34 mmol), and tetrakis(triphenylphosphine)palladium(0) (0.01 mmol) in 2M aqueous potassium carbonate solution (1.0 mL) and N,N-dimethylformamide (1.0 mL) was heated at 100 C. for 17 h. The reaction mixture was cooled, poured into water (3.0 mL), and extracted with (3*4.0 mL) ethyl acetate. The combined organic layers were dried over sodium sulfate and were concentrated in vacuo. Purification of the residue by Gilson reverse phase HPLC provided the title product as a white powder (65%). ESMS [M+H]+: 334.2.

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; SMITHKLINE BEECHAM CORPORATION; CYTOKINETICS; US2007/259951; (2007); A1;,
Bromide – Wikipedia,
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103977-79-3, name is 3-Bromo-2,4-difluoroaniline, 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. Formula: C6H4BrF2N

To a mixture of 4,4,5,5,4′,4′,5′,5′-octamethyl-[2,2′]bi[[1,3,2]dioxaborolanyl] (1.831 g, 7.21 mmol), potassium acetate (1.415 g, 14.42 mmol) and [1,1′-bis(diphenylphosphino)ferrocene]dichloropalladium(II) complexed with dichloromethane (1:1) (0.785 g, 0.962 mmol) under nitrogen was added a solution of 3-bromo-2,4-difluoroaniline (1.0 g, 4.81 mmol) in 1,4-dioxane (20 mL). The mixture was stirred at 100 C. overnight. After cooling to room temperature, the mixture was diluted with DCM and filtered through Celite. The filtrated was concentrated in vacuo. The residue was purified by Biotage Isolera (740 mg, 60%). LCMS calculated for C12H17BF2NO2 (M+H)+ m/z=256.1; found 256.1.

The synthetic route of 103977-79-3 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Incyte Corporation; Vechorkin, Oleg; Pan, Jun; Liu, Kai; Sokolsky, Alexander; Wang, Anlai; Ye, Hai Fen; Ye, Qinda; Yao, Wenqing; (167 pag.)US2018/72720; (2018); A1;,
Bromide – Wikipedia,
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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. 203302-95-8, name is 4-Bromo-3,5-difluoroaniline, A new synthetic method of this compound is introduced below., Quality Control of 4-Bromo-3,5-difluoroaniline

4-bromo-3.5-difluoro-aniline 1 g (4.81 mmol) and m-methoxyphenylboronic acid 730 mg (4.81 mmol. 1 eq)Potassium carbonate (4.82 g 24.88 mmol 6 eq) [1,1′-bis(diphenylphosphino)ferrocene]palladium dichloride (425.35 mg481 mmol 6 eq) was placed in a 100 ml two-necked flask, and 30 ml (dioxane: water = 3:1) was injected with nitrogen to protect the solution, and 80 was allowed to react for 3.5 h. After the TLC monitoring reaction is completed, the post-treatment distillation is carried out under reduced pressure to about 10 ml, and the solution is poured into a separating funnel, extracted with dichloromethane for 2-3 times, dried over anhydrous Na 2 SO 4 , filtered, and evaporated to dryness to give a black oily drop. Separated and purified by petroleum ether: ethyl acetate = 6:1 silica gel column chromatography to obtain a pale yellow oily liquid about 690 mg, yield 61%.

The synthetic route of 203302-95-8 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Sichuan University; Zhao Yinglan; Luo Youfu; Wei Yuquan; (63 pag.)CN108467370; (2018); A;,
Bromide – Wikipedia,
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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. 314084-61-2, name is 2-Bromo-1,3-diethyl-5-methylbenzene, A new synthetic method of this compound is introduced below., Safety of 2-Bromo-1,3-diethyl-5-methylbenzene

Under a nitrogen atmosphere, 14.2 g of malonic acid dinitrile are added at normal pressure and room temperature to a mixture of 67.3 g of 50% potassium hydroxide solution and 300 mi of 1-methyl-2-pyrrolidone. The reaction mixture is heated to from 60 to 100C, and 106 g of diluent are distilled off at reduced pressure (from 20 to 30 mbar). Under a nitrogen atmosphere and at normal pressure, 45.5 g of 2-bromo-1, 3-diethyl-5-methylbenzene are added. The reaction mixture is then heated to 120C with stirring, At that temperature, a mixture of 0.26 g of TRIPHENYLPHOSPHINE, 0.2 g of a commercially available palladium (LI) chloride solution in concentrated hydrochloric acid (20% Pd content corresponding to 0.071 g of palladium (II) chloride and 0.142 g of concentrated hydrochloric acid) and 19.5 g of 1-METHYL-2-PYRROLIDONE is added. Stirring is carried out at from 120 to 125C FOR 1 hour, and then a mixture of 0.26 g of triphenylphosphine, 0.2 g of a commercially available PALLADIUM (II) chloride solution in concentrated hydrochloric acid (20% Pd content corres- ponding to 0.071 g of palladium (li) chloride and 0.142 g of concentrated hydrochloric acid) and 19.5 g of 1-METHYL-2-PYRROLIDONE is again added. The reaction mixture is stirred for 3 hours at from 120 to 125C, and then a further 237 g of diluent are distilled off at reduced pressure (from 20 to 30 mbar) and at from 80 to 120C. After cooling the reaction mixture to 45C, 100 mi of toluene and 220 g of water are added and intensive stirring is carried out for 15 minutes. The two-phase mixture is transferred to a separating funnel in order to be separated. The organic phase is discarded. The aqueous phase is isolated and and 43.4 g of material are distilled off at reduced pressure (from 250 to 300 mbar) and at from 70 to 110C. 48.5 g of 32% hydrochloric acid are added in the course of from 60 to 80 minutes to the distillation sump, during the course of which the product crystallises out and the pH value falls to from 4.0 to 4.5. Suction filtration is carried out followed by washing with 130 ml of water (divided into 2 portions). The product is dried in a vacuum drying cabinet for 16 hours at from 100 to 250 mbar. 37.2 g (content 97.7% ; yield 85.7%) of 2- (2, 6-diethyl-4- methylphenyl) malonic acid dinitrile are obtained.

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; SYNGENTA PARTICIPATIONS AG; WO2004/50607; (2004); A1;,
Bromide – Wikipedia,
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Reference of 444-14-4, 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 444-14-4 as follows.

The procedure was adapted from Lemair, M. et.al . Tetrahedron, 2011 67, 1971 1976. To the solution of 2-(trifluoromethyl)aniline (1.5 g, 9.31 mmol) inacetic acid (15 mL) was added KBr (1.307 g, 10.99 mmol) and sodium perborate monohydrate (0.929 g, 9.31 mmol) and the mixture was stirred for 5 mm. To this mixture was added ammonium molybdate tetrahydrate (11.51 g, 9.31 mmol) and the reaction mixture was stirred at room temperature for 3 h. After completion of the reaction as determined by TLC, water was added and the pH was adjusted to 8 usingaq. saturated sodium bicarbonate solution. The reaction mixture was extracted with ethyl acetate (3 x 5 mL). The combined organic extracts were washed with brine solution, dried over sodium sulfate and concentrated under reduced pressure to afford 4-bromo-2-(trifluoromethyl)aniline (800 mg, 36% yield) as a yellow solid. The analytical data was consistent with the literature reference cited above.

According to the analysis of related databases, 444-14-4, the application of this compound in the production field has become more and more popular.

Reference:
Patent; BRISTOL-MYERS SQUIBB COMPANY; HARTZ, Richard A.; AHUJA, Vijay T.; BRONSON, Joanne J.; DZIERBA, Carolyn Diane; MACOR, John E.; NARA, Susheel Jethanand; RAJAMANI, Ramkumar; WO2015/6100; (2015); A1;,
Bromide – Wikipedia,
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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. 1198171-18-4, name is 1-Bromo-2-(difluoromethyl)-4-fluorobenzene belongs to bromides-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below. Quality Control of 1-Bromo-2-(difluoromethyl)-4-fluorobenzene

2-[2-(Difluoromethyl)-4-fluorophenyl]-4,4,5,5-tetramethyl-1,3,2-dioxaborolane To a solution of 1-bromo-2-(difluoromethyl)-4-fluorobenzene (31 g, 137.773 mmol, 1 equiv.) and BPD (52.48 g, 206.664 mmol, 1.50 equiv.) in 1,4-dioxane (300 mL, 3541.225 mmol, 25.70 equiv.) were added AcOK (27.04 g, 275.546 mmol, 2 equiv.) and Pd(dppf)Cl2.CH2Cl2 (5.63 g, 6.889 mmol, 0.05 equiv.) at 25 C. under nitrogen atmosphere. The mixture was stirred at 90 C. for 2 hours. The resulting mixture was concentrated under reduced pressure. The residue was purified by silica gel column chromatography, eluted with PE/EA (10/1) to afford 2-[2-(difluoromethyl)-4-fluorophenyl]-4,4,5,5-tetramethyl-1,3,2-dioxaborolane (30 g, 80.03%) as a light yellow oil. The reaction was monitored by TLC. The crude was used the next step directly.

The synthetic route of 1198171-18-4 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Goldfinch Bio, Inc.; Ledeboer, Mark W.; Daniels, Matthew H.; Yu, Maolin; Harmange, Jean-Christophe P.; US2020/102301; (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. 21524-34-5, name is 2-Bromo-1,3,5-triisopropylbenzene, A new synthetic method of this compound is introduced below., Formula: C15H23Br

1L three bottles,To a solution of 32.5 g of 2,4,6-triisopropylbromobenzene,5.6 g of magnesium turnings and 300 mL of anhydrous THF,20 g of o-chlorobromobenzene was dropwise added,2,4,6-triisopropyl-2-bromobiphenyl Grignard reagent,Refluxed for 2 hours,Down to room temperature,2.4 g of tetrakis (triphenylphosphine) palladium was added,Stirred for 30 minutes,18.8 g of di-tert-butylphosphonium chloride was added dropwise at room temperature,The reaction was refluxed for 5 hours.And the mixture was added dropwise to the reaction solution under ice-water bath200 mL of saturated aqueous ammonium chloride was quenched,Liquid separation,The organic phase is dissolved,Add methanol crystallization,And filtered to obtain 41.7 g of white 2-di-tert-butylphosphine-2,4,6-triisopropylbiphenyl,Yield 94%.

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; Panjin Gelin Kaimo Technology Co., Ltd.; Rao, Zhihua; Gong, Ningrui; (12 pag.)CN105859774; (2016); A;,
Bromide – Wikipedia,
bromide – Wiktionary