Month: March 2021

Electric Literature of 553-94-6, These common heterocyclic compound, 553-94-6, name is 2,5-Dimethylbromobenzene, 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.

General procedure: To a flask containing Mg turnings (0.29 g, 12 mmol) was added1-bromo-4-methylbenzene (1.37 g, 8.0 mmol) in THF (8 mL) at room temperature. After being stirred for 2 h, DMF (1.3 mL,12 mmol) was added to the reaction mixture. The obtained mixturewas stirred for 2 h at 0 C. Then, aq NH3 (7 mL, 28-30%) and I2 (4.06 g, 16 mmol) were added to the reaction mixture. After beingstirred for 2 h at room temperature, the reaction mixture waspoured into satd aq Na2SO3 solution and was extracted with CHCl3 (3*30 mL). The organic layer was dried over Na2SO4 and filtered.After removal of the solvent, the residue was purified by shortcolumn chromatography on silica gel (eluent: hexane/ethylacetate=9:1, v/v) to provide pure 4-methyl-1-benzonitrile (0.77 g) in 82% yield.

The synthetic route of 553-94-6 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Ishii, Genki; Harigae, Ryo; Moriyama, Katsuhiko; Togo, Hideo; Tetrahedron; vol. 69; 5; (2013); p. 1462 – 1469;,
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. 5469-19-2, name is 1-Bromo-2,4,5-trimethylbenzene, This compound has unique chemical properties. The synthetic route is as follows., category: bromides-buliding-blocks

Example 2 This example illustrates the preparation of a triarylaminehaving Formula II I, 4′,4″-(diphenylmethylene)bis(N,N-bis(2,4,5- trimethylphenyl)biphenyl-3-amine), Compound 1 . Compound 1 In a dry box, 4′,4″-(diphenylmethylene)dibiphenyl-3-amine (0.95 g,1 .80 mmol), 1 -bromo-2,4,5-trimethylbenzene (1 .52 g, 7.58 mmol), tris(tert- butyl)phosphine (0.029 g, 0.144 mmol) and Pd2(DBA)3 (0.066 g, 0.072 mmol) were combined in round bottom flask and dissolved in 35 ml of dry toluene. The solution was stirred for a minute and followed by sodium tert- butoxide (0.76 g, 7.94 mmol) and 5 ml of dry toluene. A heating mantle was added and the reaction heated to 60C for 18 hour. The reaction mixture was then cooled to room temperature and filtered, washing with chloroform. The solvent was removed by rotary evaporation and the residue was purified further by silica gel column chromatography using a gradient of chloroform in hexanes (0-36%). The product containing fractions were collected and combined. The solvent was removed by rotary evaporation. The residue was crystallized from dichloromethane and ethanol to give 1 .20 g (68%) product as a white powder. 1 H NMR (CDCI3) is consistent with the structure for Compound 1 .

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 5469-19-2.

Reference:
Patent; E. I. DU PONT DE NEMOURS AND COMPANY; WANG, Ying; WU, Weishi; DOBBS, Kerwin, D.; WO2011/49904; (2011); A2;,
Bromide – Wikipedia,
bromide – Wiktionary

Electric Literature of 138526-69-9, The chemical industry reduces the impact on the environment during synthesis 138526-69-9, name is 1-Bromo-3,4,5-trifluorobenzene, I believe this compound will play a more active role in future production and life.

Intermediate T(l)(lS,2R)-2-(3,4,5-Trifluorophenyl)cyclopentanolTo a suspension of magnesium (2.88 g, 118 mmol) in THF (1 10 mL) was slowly added 5-bromo-l,2,3-trifluorobenzene (25 g, 118 mmol). After the addition, the reaction mixture was heated at reflux for 2 h. To this reaction mixture, copper (I) iodide (1.506 g, 7.91 mmol) and 6-oxabicyclo[3.1.0]hexane (9.93 g, 118 mmol) dissolved in THF (20 mL) were added dropwise. The reaction mixture warmed upon the addition of the epoxide. The reaction was stirred at rt for 2 h at rt. The reaction mixture was quenched by the addition of a solution of ammonium chloride. Ether was added and the organic layer was collected, dried ( a2S04) and concentrated. The crude product was purified by column chromatography on silica gel to give (l S,2R)-2-(3,4,5-trifluorophenyl)cyclopentanol (20.2 g, 93 mmol, 79 % yield).? NMR (500 MHz, CDC13) delta ppm 6.79 – 7.02 (2H, m), 4.10 – 4.21 (1H, m), 2.75 – 2.91 (1H, m), 2.08 – 2.24 (2H, m), 1.75 – 1.93 (2H, m), 1.50 – 1.75 (2H, m).

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-3,4,5-trifluorobenzene, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; BRISTOL-MYERS SQUIBB COMPANY; BOY, Kenneth M.; GUERNON, Jason M.; MACOR, John E.; OLSON, Richard E.; SHI, Jianliang; THOMPSON, Lorin A., III.; WU, Yong-Jin; XU, Li; ZHANG, Yunhui; ZUEV, Dmitry S.; WO2012/103297; (2012); A1;,
Bromide – Wikipedia,
bromide – Wiktionary

Application of 337915-79-4, A common heterocyclic compound, 337915-79-4, name is 5-Bromo-N1-methylbenzene-1,2-diamine, molecular formula is C7H9BrN2, 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.

[000849j To a stirred solution of compound 3 (1 g, 1 eq) in POC13 (2 mL), cyclopropane carboxylic acid (0.5 mL) were added. The resulting reaction mixture was heated at 120 C for 3h. The progress of the reaction was monitored by TLC. After completion of the reaction, the reaction mixture was quenched with saturated sodium bicarbonate solution and extracted with ethyl acetate (3 X 20 mL). Combined organic extracts were washed with brine, dried over anhydrous sodium sulfate and evaporated under reduced pressure. The crude product was purified by column chromatography on silica gel 100-200 mesh using 20% EtOAc-hexane to afford the title compound 4. LCMS (mlz): 250.95 (M + 1).

The synthetic route of 337915-79-4 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; BIOMARIN PHARMACEUTICAL INC.; BHAGWAT, Shripad; WANG, Bing; LUEDTKE, Gregory R.; SPYVEE, Mark; (490 pag.)WO2016/57834; (2016); A1;,
Bromide – Wikipedia,
bromide – Wiktionary

Synthetic Route of 399-94-0, A common heterocyclic compound, 399-94-0, name is 1-Bromo-2,5-difluorobenzene, molecular formula is C6H3BrF2, 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.

Method A:To a nitrogen degassed, light brown solution of 2-bromo-1,4-difluorobenzene (48.3 mL, 0.429 mol) in CH2Cl2 (500 mL) was added i-PrMgCl (2.0 M in THF, 205 mL, 0.41 mol) slowly while the internal temperature was maintained below -15 C. The resulting reaction mixture was aged for additional 30 min. In a separate 500-mL round bottom flask, the Weinreb amide 4 (50 g, 0.195 mol) was dissolved in CH2Cl2 (300 mL) and cooled to -15 C. The Weinreb amide solution was transferred to the above aryl Grignard solution via cannula over 1 h such that temperature was less than -15 C. The reaction mixture was allowed to warm to room temperature upon completion of addition and aged overnight. The reaction mixture was quenched into a 3-L round bottom flask containing 1.2 L of half-saturated aqueous NH4Cl via cannula. The pH of the solution was then adjusted to 7 with concentrated HCl. Upon separation of the layers, the organic layer was dried over MgSO4 in preparation for isolation.

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; Xu, Feng; Kim, Mary M.; Kohmura, Yoshinori; Sladicka, Tricia; Rosen, Jonathan D.; Zacuto, Michael J.; US2009/187028; (2009); A1;,
Bromide – Wikipedia,
bromide – Wiktionary

These common heterocyclic compound, 556-96-7, name is 1-Bromo-3,5-dimethylbenzene, 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. name: 1-Bromo-3,5-dimethylbenzene

Under an argon atmosphere, a solution of magnesium (25 g, 0.95 equivalent) and a small amount of iodine in THF (250 mL) was stirred at room temperature for 1 hr. 5-Bromo-m-xylene (200 g, 1.08 moL) was added at 48C, and the mixture was stirred at 5C for 1 hr. Diethyl phosphite (78.3 g, 0.52 equivalent) was added at 5C, and the mixture was stirred at 5C for 2 hrs. Water (200 mL) was added at 3C, and toluene (200 mL) and 6M-HCl (160 mL) were added. The mixture was stirred at room temperature for 30 min. The reaction mixture was partitioned, and the organic layer was washed successively with water (100 mL), 5% aqueous NaHCO3 solution (100 mL) and 5% aqueous NaCl solution (100 mL). The organic layer was dried over anhydrous magnesium sulfate and filtered by gravity. The filtrate was concentrated under reduced pressure and the residue was recrystallized from diisopropyl ether-heptane to give the title compound (43.3 g, white crystals). yield 33.3%.

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

Reference:
Patent; Takeda Chemical Industries, Ltd.; EP1452537; (2004); 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. 1074-24-4, name is 1,4-Dibromo-2,5-dimethylbenzene, A new synthetic method of this compound is introduced below., Formula: C8H8Br2

Under a nitrogen stream 2,5-dibromo-p-xylene (25.0 g, 94.71 mmol) is added to diethylether (350 mL), the temperature is lowered to -78 ¡ã C, and then 2.5 M n-BuLi (31.5 g, 113.6 mmol) is added slowly. After the temperature was raised to room temperature, the mixture was stirred for 1 hour, and then DMF (8.3 g, 113.65 mmol) was added slowly at -78 ¡ã C, followed by stirring at room temperature for 12 hours. To terminate the reaction, the reaction mixture is poured into water and extracted with diethylether. The organic layer is washed with MgSO4 to remove water and the solvent is removed. A white solid was obtained using a silica column (Hexane). (15.6 g, 71percent). 1H NMR (300 MHz, CDCl3, delta): 10.12(s, 1H), 7.38(s, 1H), 7.30(s, 1H), 2.35(s, 6H).

The synthetic route of 1074-24-4 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Korea Institute of Industrial Technology; Lee, Young Chul; Kim, Myung Jun; Kim, Baek Jin; Hwang, Suk Ho; Jung, Sung Wook; Kim, Chang Joo; (13 pag.)KR101610235; (2016); B1;,
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 6274-57-3 as follows. Product Details of 6274-57-3

. Example 10. Synthesis of tributyl[{(4-dimethylamino)methyl}phenyl]stannane (S8)”BuLi To (4-bromobenzyl)dimethylamine (2.14 g, 10.0 mmol, 1.00 equiv) in Et2O (25 niL) at 23 0C was added “BuLi (2.4 M in hexane, 4.17 niL, 10 mmol, 1.0 equiv). The reaction mixture was warmed to 23 0C and stirred for 2.0 hr before the addition of “Bu3SnCl (3.25 g, 10.0 mmol, 1.00 equiv) at -78 0C. After stirring for 1.0 hr at 23 0C, the reaction mixture was concentrated in vacuo. The residue was purified by chromatography on silica gel eluting with hexanes/EtOAc 1:1 (v/v) to afford 3.35 g of the title compound as a colorless oil (79% yield). R/= 0.20 (hexanes/EtOAc 1:1 (v/v)). NMR Spectroscopy: 1H NMR (500 MHz, CDCl3, 23 0C, delta): 7.42 (d, / = 6.5 Hz, 2H), 7.27 (d, / = 6.5 Hz, 2H), 3.41 (s, 2H), 2.26 (s,6H), 1.64-1.48 (m, 6H), 1.40-1.30 (m, 6H), 1.15-0.99 (m, 6H), 0.90 (t, / = 6.0 Hz, 9H). 13C NMR (100 MHz, CDCl3, 23 0C, delta): 140.30, 138.40, 136.36, 128.72, 64.40, 45.36, 29.07, 27.35, 13.64, 9.52. Mass Spectrometry: HRMS-FIA (m/z): Calcd for [M + H]+, 426.21772. Found, 426.21651.

According to the analysis of related databases, 6274-57-3, the application of this compound in the production field has become more and more popular.

Reference:
Patent; PRESIDENT AND FELLOWS OF HARVARD COLLEGE; RITTER, Tobias; FURUYA, Takeru; TANG, Pingping; WO2010/59943; (2010); A2;,
Bromide – Wikipedia,
bromide – Wiktionary

Related Products of 55289-36-6, A common heterocyclic compound, 55289-36-6, name is 3-Bromo-2-methylaniline, molecular formula is C7H8BrN, 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.

Intermediate 20-1Preparation of N-(3-bromo-2-methylphenyl)-1H-indazol-3-amine Step 1 A mixture of 3-bromo-2-methylaniline (1.66 mL, 13.4 mmol), 2-fluorobenzoic acid (1.883 g, 13.4 mmol), and HOAT (2.74 g, 20.2 mmol) in EtOAc (60 mL) was treated with DIEA (4.7 mL, 26.9 mmol) and EDC (5.15 g, 26.9 mmol) and the mixture was stirred at rt. After 19 h, the mixture was diluted with EtOAc and washed with water, 1 M hydrochloric acid (twice), NaHCO3 (aq) (twice) and brine, dried and concentrated to provide N-(3-bromo-2-methylphenyl)-2-fluorobenzamide as tan fluffy needles (4.11 g, 99%). 1H NMR (400 MHz, chloroform-d) delta 8.34-8.50 (1 H, m), 8.20 (1H, td, J=7.9, 1.8 Hz), 7.96 (1H, d, J=8.1 Hz), 7.50-7.59 (1H, m), 7.44 (1H, dd, J=8.0, 0.8 Hz), 7.30-7.37 (1H, m), 7.21 (1H, dd, J=12.8, 7.9 Hz), 7.12 (1H, t, J=8.0 Hz), 2.45 (3H, s). Mass spectrum m/z 308, 310 (M+H)+.

The synthetic route of 55289-36-6 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Bristol-Myers Squibb Company; US2010/160303; (2010); A1;,
Bromide – Wikipedia,
bromide – Wiktionary

Adding a certain compound to certain chemical reactions, such as: 10485-09-3, name is 2-Bromoindene, 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 10485-09-3, Formula: C9H7Br

A 1.45 g (59.8 mmol) piece of magnesium was charged into a sufficiently dried and argon-substituted 200 mL reactor, and stirred vigorously for 30 minutes while heating under reduced pressure. After cooling to room temperature, a reflux condenser was attached, and a piece of iodine and 15 mL of tetrahydrofuran were charged and stirred. A solution of 2.93 g (15.0 mmol) of 2-bromoindene in 15 mL of a diluted solution of tetrahydrofuran is added dropwise (1.0 mL added, followed by heating under reflux with a dryer until the color of iodine disappears, remaining drop after reaction starts) It stirred at room temperature after completion | finish for 2 hours.The reaction solution is diluted with 9.00 mL (75.3 mmol) of dimethylsilyl dichloride in 10 mL of n-hexane diluted solution.The reaction was slowly added at -78 C with cooling, and stirring was continued for 19 hours while returning to room temperature.After distilling off the solvent of the reaction solution and unreacted dimethylsilyl dichloride, 10 mL of tetrahydrofuran and 1.50 mL (16.0 mmol) of 1,3-dimethyl-2-imidazolidinone were added to the residue. In a fully dried, argon purged 100 mL reactor, obtained in Synthesis Example 5-15.62 g (15.0 mmol) of the selected compound (A-5a) and 15 mL of tetrahydrofuran are added, 9.70 mL (hexane solution, 1.55 M, 15.0 mmol) of n-butyllithium solution is added, and the mixture is stirred at room temperature for 2 hours did. The above reaction was cooled to -78 C.The residue was added dropwise to the diluted solution, and stirring was continued for 45 hours while slowly returning to room temperature. Saturated aqueous ammonium chloride solution was added, the extract was extracted with ethyl acetate, and the obtained fraction was washed with saturated brine and dried over anhydrous magnesium sulfate. After filtering the magnesium sulfate, the filtrate is distilled offThe residue thus obtained was purified by silica gel column chromatography to obtain 7.67 g (yield: 94%) of the target product (hereinafter referred to as compound (A-5L)) represented by the following formula (A-5L) It was obtained as a body mixture.

If you are interested in these compounds, you can also browse my other articles.Thank you for taking the time to read this article. I hope you enjoyed it.

Reference:
Patent; Mitsui Chemicals, Inc.; Prime Polymer Co., Ltd.; Tanaka, Yoichi; Harada, Yasuyuki; Tamura, Naoya; Hato, Ikki; Tsuchitani, Hiroko; (68 pag.)JP2019/59723; (2019); A;,
Bromide – Wikipedia,
bromide – Wiktionary