Month: June 2021

Adding a certain compound to certain chemical reactions, such as: 937046-98-5, name is 7-Bromopyrrolo[2,1-f][1,2,4]triazin-4-amine, 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 937046-98-5, Quality Control of 7-Bromopyrrolo[2,1-f][1,2,4]triazin-4-amine

To a dry, argon purged round bottom flask (100 mL) were added 7-bromo- pyrrolo[2, 1 -f] [ 1 ,2,4]triazin-4-ylamine (234 mg, 1.10 mmol) (prepared according to WO2007056170) and anhydrous THF (1.5 mL). TMSCI (276 mu, 2.2 mmol) was then added and the reaction mixture stirred for 2 h. The flask was placed into a dry ice/acetone bath (~ -78 C) and BuLi (2.5 mL, 4.0 mmol, 1.6M in hexanes) was added dropwise. After lh, a solution of If (432.5 mg, 1.0 mmol) in THF was cooled to 0 C and then added to the reaction flask dropwise. After 1 h of stirring at -78 C, the flask was warmed to 0 C and sat. NH4C1 (5 mL) was added to quench the reaction. The organics were extracted using EtOAc (3 10 mL) and the combined organic layers were dried using MgS04. The solvent was removed under reduced pressure and the crude material was purified using flash chromatography (hexanes / EtOAc). 560 mg (90 %) of 2a was isolated as a mixture of two anomers. LC/MS = 567.2 (M + H+). ]H NMR (300 MHz, CDC13): delta 7.85 (m, IH), 7.27 (m, 15H), 7.01 (m, 1H), 6.51 (m, 1H), 4.66 (m, 8H), 4.40 (m, 2H), 3.79 (m, 3H), 1.62 (s, 2′-CH3 from the one anomer), 1.18 (s, 2′-CH3 from the other anomer).

At the same time, in my other blogs, there are other synthetic methods of this type of compound, 7-Bromopyrrolo[2,1-f][1,2,4]triazin-4-amine, and friends who are interested can also refer to it.

Reference:
Patent; CHO, Aesop; CLARKE, Michael, O’neil Hanrahan; WOLCKENHAUER, Scott, Alan; GILEAD SCIENCES, INC.; WO2012/12465; (2012); A1;,
Bromide – Wikipedia,
bromide – Wiktionary

Synthetic Route of 626-39-1, 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. 626-39-1 name is 1,3,5-Tribromobenzene, 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.

1,3,5-Tribromobenzene (20 g, 62 mmol), Pd(PPh3)4 (3.57 g, 3.1mmol) were added to 300 mL of dry THF solution, thenphenylbronic acid (32 g, 155 mmol) and 2 M K2CO3 solution (50 mL), which was dissolved in H2O, was added to the reaction mixture. The reaction mixture was heated to 65C for 5 h under nitrogen. After the reaction was finished,extracted with diethyl ether and water. The organic layer was dried with anhydrous MgSO4 and filterd. The solvent was evaporated. The product was isolated by silica gel column chromatography using CHCl3:hexane (1:15) eluent to afforda white solid (Yield 61%). 1H NMR (300 MHz, CDCl3) delta 7.7(s, 3H), 7.6 (d, 4H), 7.45 (t, 4H), 7.4 (t, 2H).

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

Reference:
Article; Shin, Hwangyu; Kang, Hyeonmi; Kim, Beomjin; Park, Youngil; Yu, Young-Jun; Park, Jongwook; Bulletin of the Korean Chemical Society; vol. 35; 10; (2014); p. 3041 – 3046;,
Bromide – Wikipedia,
bromide – Wiktionary

Reference of 1074-24-4, 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 1074-24-4 as follows.

Iodine (78 mg, 0.33 mmol) was added to p-xylene (6.13 mL, 50.0 mmol), the mixture was cooled to 0 °C, and bromine (5.20 mL, 101 mmol) was added dropwise over 10 min. The ice bath was removed and the reaction stirred at rt for 16 h in the absence of light. The reaction was quenched with 20percent aq. KOH and stirred for 15 min while the solution became colorless. The solid precipitate was filtered and rinsed 2 x with 100 mL of H2O. The solids were recrystallized in ethanol to afford a white solid (9.19 g, 70percent). 1H NMR (CDCl3): delta 7.40 (s, 2H), 2.34 (s, 6H). 1,4?dibromo-2,5-dimethylbenzene (5.93 g, 22.5 mmol) and KMnO4 (15.72 g, 99.5 mmol) were added to 80 mL of t-BuOH:H2O (1:1). Celite (14 g) was added to the flask and the reaction was refluxed for 18 h. The reaction mixture was cooled to rt, filtered over celite and the filter was washed with hot H2O (100mL) and EtOAc (50mL). The filtrate was then acidified to pH=1 with conc. HCl. The white suspension was then extracted 3x with 100 mL of EtOAc. The combined organic extracts were dried over MgSO4 and excess solvent was removed under vacuum to obtain a white solid (3.06 g, 42percent) which was not purified further. 1H NMR (DMSO-d6): delta 8.01 (s, 2H). 2,5?dibromoterephthalic acid (2.04 g, 6.30 mmol) dissolved in 35 mL of MeOH and refluxed for 30 min. Thionyl chloride (9.00 mL, 124 mmol) was then carefully added and the reaction was refluxed 12 hours. The reaction flask was cooled to room temperature, 50 mL of water was carefully added, and the reaction was extracted 3x with 75 mL of Et2O. The combined organics were washed with 3 x with 50 mL of sat. NaHCO3 and dried with MgSO4. The solvent was removed under vacuum and the solids recrystallized in MeOH to yield a white crystalline solid (1.65g, 74percent), mp = 134-136 C (lit.3 mp 134-137 C). 1H NMR (CDCl3): delta 8.06 (s, 2H), 3.96 (s, 6H). The 1H NMR matches the known spectrum.3

According to the analysis of related databases, 1074-24-4, the application of this compound in the production field has become more and more popular.

Reference:
Article; Dressler, Justin J.; Miller, Sarah A.; Meeuwsen, Brian T.; Riel, Asia Marie S.; Dahl, Bart J.; Tetrahedron; vol. 71; 2; (2015); p. 283 – 292;,
Bromide – Wikipedia,
bromide – Wiktionary

Related Products of 1003-98-1, These common heterocyclic compound, 1003-98-1, name is 2-Bromo-4-fluoroaniline, 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.

Reference Example 10: methyl [(lR)-6-fluoro-8-(methylsulfonyl)-2, 3,4, 9-tetrahydro-lH-carbazol-l- yl] acetate Step 1: 2-(2-bromo-4-fluorophenyl) hydraziniumchloride To a suspension of 2-bromo-4-fluoroaniline in concentrated HCI (1. 5M) at-10 C was slowly added a 10. 0M aqueous solution of NaNO2 (1.1 eq). The mixture was stirred at 0 C for 2.5 hrs. A cold (-30 C) solution of SnCl2 (3. 8M) in concentrated HCI was then slowly added while maintaining the internal temperature below 10 C. The resulting mixture was stirred mechanically for 20 min at 0, then at room temperature for 1 hr. The thick slurry was filtered and the solid was air dried overnight. The solid was resuspended in cold HCI and filtered again. The dried material was suspended in Et2O, stirred for 10 min, filtered and air dried overnight to give the title compound as a beige solid.

Statistics shows that 2-Bromo-4-fluoroaniline is playing an increasingly important role. we look forward to future research findings about 1003-98-1.

Reference:
Patent; MERCK FROSST CANADA & CO.; WO2005/56527; (2005); A1;,
Bromide – Wikipedia,
bromide – Wiktionary

Synthetic Route of 615-54-3, 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. 615-54-3, name is 1,2,4-Tribromobenzene, This compound has unique chemical properties. The synthetic route is as follows.

6.296 (0.02 mol) 1,2,4-tribromobenzene and 8.671 g (0.05 mol)3-aminobenzeneboronic acidHydrochlorideAdd to a 500 mL three-necked flask, add 400 mL of tetrahydrofuran (THF), and add 45 mL of 2 mol/L potassium carbonate solution.And add an appropriate amount of aliquat336, magnetically stirred and argon gas, after heating to 75 C in the oil bath,0.020 g of tetrakistriphenylphosphine palladium was added, and the reaction was refluxed for 24 hours, and the reaction liquid was poured into water to precipitate a large amount. The mixture was filtered with a funnel, and the solvent was evaporated under reduced pressure.The product was purified by column chromatography using dichloromethane: n-hexane = 2:1 (volume ratio) as mobile phase as the stationary phase. The product was collected and dried.Drying in a vacuum at 90 C for 24 h,The target product was obtained 5.834 g,The yield was 83%.

The chemical industry reduces the impact on the environment during synthesis 1,2,4-Tribromobenzene. I believe this compound will play a more active role in future production and life.

Reference:
Patent; Hunan University of Technology; Ke Shenghai; Liu Yiwu; Tan Jinghua; Zhu Heping; (19 pag.)CN108976138; (2018); A;,
Bromide – Wikipedia,
bromide – Wiktionary

Adding a certain compound to certain chemical reactions, such as: 24358-62-1, name is 1-(4-Bromophenyl)ethylamine, 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 24358-62-1, Application In Synthesis of 1-(4-Bromophenyl)ethylamine

To a solution of 2-bromoacetamide 6 (827mg, 5.88 mmol), and 4-bromobenzylethylamine 15 (1.00 g, 4.90 mmol) in MeOH (5ml) and CH2Cl2 (5ml) at room temperature was added Hunig’s base (5ml). The mixture was stirred at 50-60 C for 16h. Water (30mL) was added and the mixture was extracted with CH2Cl2 (4 x 30ml) and dried over Na2SO4 to provide 1.27 g amide 16 as white crystals in 100% yield. This product was used without further purification in the next step. 1HNMR (300 MHz, CDCl3, ppm): delta 7.38 (d, J=8Hz, 2H), 7.09 (d, J=8Hz, 1H), 6.77 (s br, 1H), 5.69 (s br, 1H), 3.67 (q, J=7Hz, 1H), 3.07 (s, 2H), 1.29 (d, J=7Hz, 3H).

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

Reference:
Patent; RIB-X PHARMACEUTICALS, INC.; WO2005/12270; (2005); A2;,
Bromide – Wikipedia,
bromide – Wiktionary

Reference of 73918-56-6,Some common heterocyclic compound, 73918-56-6, name is 2-(4-Bromophenyl)ethanamine, 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.

1. BOC2O (818 mg, 3.75 mmol, 1.5 eq.) was added to a stirred solution of 2-(4- bromophenyl)ethanamine (500 mg, 2.5 mmol, 1.0 eq.) and TEA (1.5 ml, 7.5 mmol, 3.0 eq.) in DCM (25 ml) at 0 0C and resulting reaction mixture is stirred at 25 0C for 6 h. The reaction mixture was diluted with DCM (75 ml), washed with water (2 x 50 ml) and brine (50 ml) and dried over Na2SO4. The solvent was evaporated under reduced pressure and the residue triturated with hexanes to yield the desired product as an off white solid.Yield: 100 % (750 mg, 2.5 mmol)

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 2-(4-Bromophenyl)ethanamine, its application will become more common.

Reference:
Patent; GRUeNENTHAL GMBH; MERLA, Beatrix; OBERBOeRSCH, Stefan; REICH, Melanie; SCHUNK, Stefan; JOSTOCK, Ruth; HEES, Sabine; ENGELS, Michael; GERMANN, Tieno; BIJSTERVELD, Edward; WO2010/99938; (2010); A1;,
Bromide – Wikipedia,
bromide – Wiktionary

Synthetic Route of 2270-59-9, 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. 2270-59-9, name is 5-Bromo-2-methylpent-2-ene, This compound has unique chemical properties. The synthetic route is as follows.

1.55 kg of magnesium and 10 kg of THF are charged into a stainless steel reactor provided with liquid nitrogen cooling . This is heated under reflux (60-700C) and, still at that temperature, 0.5 I of the solution containing 10 kg of 5-bromo-2-methyl- pentene (II) at 100% is poured. This is kept under reflux for at least 10 minutes until the reaction starts. The reaction mixture is then cooled to 50-600C and, keeping it at that temperature with a brine bath, the remaining solution of 5-bromo- 2-methyl-pentene (II) in THF is poured. The reaction mixture is kept at 50-600C for at least 1.5 hours and 40 kg of THF are added. The reaction mixture is then cooled with liquid nitrogen to -65/-700C and at that temperature 7.2 kg of diethyloxalate are added. The reaction mixture is kept at -65/-700C for at least 1 hour, under EPO stirring. The mixture thus obtained is then poured into another enamelled reactor containing 10kg of 32% hydrochloric acid dissolved in 30 kg of demineralised water and previously cooled to 0-100C.The reaction mixture is then brought to 20-300C and left until the phases separate. The aqueous phase is removed, while the organic phase is washed at 20-300C with 0.25 kg of sodium bicarbonate dissolved in 5 kg of demineralised water. The reaction mixture is stirred at the same temperature and left until the phases separate. The lower aqueous phase is removed, while the solvent is removed from the organic phase by vacuum distillation until an oily residue is obtained. Then 15 kg of THF are added and the mixture obtained is stirred until a solution is obtained which is sent to the next stage. Yield not determined.

The chemical industry reduces the impact on the environment during synthesis 5-Bromo-2-methylpent-2-ene. I believe this compound will play a more active role in future production and life.

Reference:
Patent; ERREGIERRE S.p.A.; STRAGEN PHARMA SA; WO2007/9953; (2007); A1;,
Bromide – Wikipedia,
bromide – Wiktionary

Synthetic Route of 626-40-4,Some common heterocyclic compound, 626-40-4, name is 3,5-Dibromoaniline, molecular formula is C6H5Br2N, 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.

The 5.018 (0.02 muM) 3, 5 – dibromoaniline and 9.350 g (0.05 muM) (6 – aminonaphthalen – 2 – yl) boronic acid is added to a 500 ml three-neck bottle in, adding 400 ml tetrahydrofuran (THF), then adding 2 mol/L potassium carbonate solution of 75 ml, and add 0.5 ml of aliquat 336, magnetic stirring and open the argon gas, oil bath is heated to 75 C after, adding 0.020 g […] palladium, reflux reaction 24 h, the reaction liquid is poured into the water in the, a large amount of precipitate out. For funnel, evaporating the solvent under reduced pressure. The product in order to dichloromethane: hexane=3:1 ([…]) as the mobile phase silica gel as stationary phase makes the column chromatographic purification, collecting products and turns on lathe does, in 90 C drying in vacuum 24 h, to obtain the target product 5.632 g, yield is 75%.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 3,5-Dibromoaniline, its application will become more common.

Reference:
Patent; Hunan University of Technology; Ding Qian; Tan Jinghua; Liu Yiwu; Fu Hao; (20 pag.)CN109053466; (2018); A;,
Bromide – Wikipedia,
bromide – Wiktionary

These common heterocyclic compound, 2924-09-6, name is 5-Bromo-2-fluoroaniline, 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. category: bromides-buliding-blocks

5-Bromo-2-fluoroaniline (2.85 g, 15.00 mmol) and 4-methylmorpholine (1.65 mL, 15.00 mmol) were dissolved in anhydrous dichloromethane (20 mL) and the solution was cooled to -20 C. Add compound 5 (3.55 g, obtained in the synthesis of steps 1-3,13.66 mol), the mixture was slowly warmed to 20 C and kept stirring at 20 C for 12 hours. The resulting red suspension was poured into water (80 mL). The phases were separated and the organic layer was dried with Na2SO4, filtered and evaporated.A red oil was obtained and the residual red oil was dissolved in methanol (20 mL).The solution was heated to reflux for 1 hour to form a precipitate. The mixture was cooled to 4 C.The precipitate was collected by filtration, washed with methanol and dried to give a pale pink solid.N-(5-Bromo-2-fluorophenyl)-6-(furan-2-yloxy)pyridine-3-sulfonamide (Compound 6), 3.50 g, yield 62%.

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

Reference:
Patent; Dou Yuling; (11 pag.)CN108484585; (2018); A;,
Bromide – Wikipedia,
bromide – Wiktionary