Month: July 2021

Application of 7745-91-7, A common heterocyclic compound, 7745-91-7, name is 3-Bromo-4-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.

Example 2; (3’R,4’S,5’S,6’R,7S)-1-[(4-ethylphenyl)methyl]-6′-hydroxymethyl-3′,4′,5′,6′-tetrahydro-spiro[furo[3,4,f]indole-7(5H),2′-[2H]pyran]-3′,4′,5′-triol; 1) Synthesis of (3-bromo-4-methylphenyl)-(2,2-diethoxyethyl)-amine; [Show Image] Under a nitrogen stream, a mixture of 3-bromo-4-methyl-phenylamine (4.94 g, 26.55 mmol), bromoacetaldehyde diethyl acetal (6.80 g, 34.50 mmol), triethylamine (5.37 mL, 38.53 mmol) and ethanol (10.3 mL) was stirred for 2 hours at 150C using a microwave apparatus. The resultant solution was cooled to room temperature, and then water was added thereto. The resultant mixture was extracted with dichloromethane. The organic layer was dried over anhydrous magnesium sulfate, and then concentrated under reduced pressure. The resulting residue was purified by silica gel flash column chromatography (developing solution = ethyl acetate:n-hexane (1:10)), to thereby obtain the titled compound (6.43 g, 80%). 1H-NMR (CDCl3) delta: 1.17-1.28 (6H, m), 2.27 (3H, s), 3.18-3.77 (6H, m), 3.80 (1H, bs), 4.61-4.68 (1H m), 6.49 (1H, dd, J = 2.47, 8.23 Hz), 6.83 (1H, d, J = 2.47 Hz), 6.99 (1H d, J = 8.23 Hz).

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; CHUGAI SEIYAKU KABUSHIKI KAISHA; EP2048152; (2009); A1;,
Bromide – Wikipedia,
bromide – Wiktionary

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. 327-52-6, name is 1-Bromo-2,4,5-trifluorobenzene belongs to bromides-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below. name: 1-Bromo-2,4,5-trifluorobenzene

Into a 100 mL three-necked flask were added 4.62 g 1-bromo-2,4,5-trifluorobenzene (0.022 mol) and anhydrous tetrahydrofuran (50 mL). The resulting mixture was cooled to -20 C. The solution of isopropylmagnesium bromide (22 mmol) in tetrahydrofuran (22 ml, 1M THF) was slowly added dropwise under nitrogen. After the addition was complete, the reactants were maintained at -20 C. for later use. Cuprous bromide-dimethyl sulfide (0.41 g, 0.002 mol) was suspended in 5 ml anhydrous tetrahydrofuran. The resulting mixture was cooled to -5 C. The Grignard reagent as described above was slowly added dropwise under nitrogen. After 15 min, a solution of the aziridine compound as shown in the above reaction formula (4.16 g, 0.015 mol) in 30 mL tetrahydrofuran was slowly added dropwise. After additional 5 min, 50 mL saturated solution of ammonia chloride was added to quench the reaction. Into this obtained solution was added 50 mL ethyl acetate. The separated water layer was extracted with another 50 mL ethyl acetate. The obtained organic layers were collected together and further was washed with saturated solution of sodium chloride and then dried over anhydrous sodium sulfate, followed by filtration and concentration to obtain a crude product, which was further treated by column chromatography to obtain a compound (4.98 g, 0.0128 mol, yield 85%). 1H NMR (400 MHz, CDCl3) delta 7.877.61 (m, 5H), 7.156.94 (m, 1H), 6.88 (d, J=6.8 Hz, 1H), 5.02 (d, J=8.9 Hz, 1H), 4.00-3.80 (m, 1H), 2.922.76 (m, 1H), 2.762.64 (m, 1H), 2.642.44 (m, 2H), 2.06 (d, J=14.6 Hz, 3H), 1.84 (s, 1H), 1.62 (s, 1H). Ms (M++1): 390.

The synthetic route of 327-52-6 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; ZHEJIANG HISOAR PHARMACEUTICAL CO., LTD.; Pan, Xianhua; Li, Weijin; Zhang, Qunhui; Ruan, Libo; Yu, Wansheng; Deng, Fei; Ma, Tianhua; Huang, Mingwang; He, Minhuan; US2013/281695; (2013); 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. 1073-06-9, name is 1-Bromo-3-fluorobenzene, A new synthetic method of this compound is introduced below., Application In Synthesis of 1-Bromo-3-fluorobenzene

General procedure: An argon filled 50 mL two-necked flask equipped with stir barand a gas condenser was charged with magnesium turnings(165 mg, 6.800 mmol). After three successive vacuum/argon cycles,THF (15 mL) and one grain of iodine were added, and brownishsuspension was stirred for 15 min at room temperature. Subsequentlyfluorinated bromobenzene (6.700 mmol) was added. Anexothermic reaction was followed by changes of the color of thereaction mixture from original brown, through colorless to finalgrayish. This suspension was stirred 2 h at room temperature andthen cooled to 50 C. A white solid precipitated. Subsequently,methyl 2-formylbenzoate (20) (500 mg, 3.046 mmol) was addedinto vigorously stirred suspension. Cooling was stopped and thereaction mixture was slowly allowed to reach room temperatureand then stirred for additional 16 h. The suspension dissolved atca 5 C leaving dark red solution, which then slowly changed colorto orange and the dense yellowish solid slowly precipitated duringsubsequent stirring. Then Ac2O (4 mL) was added dropwise (thesuspension dissolved leaving a clear yellow/orange solution) andthe reaction mixturewas refluxed at the temperature of the oil bath 70 C for additional 30 min. A dense yellowish precipitate wasformed again. Yellow suspension was cooled to room temperature,diluted with ether (100 mL), and washed with a saturated aqueoussolution of NaHCO3 (3 15 mL). Deep yellow organic phase wasdried over MgSO4. Solvents were removed under reduced pressureand column chromatography on silica gel (hexane/ethyl-acetate -4:1) afforded products as yellow crystalline solids.

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:
Article; Kaleta, Ji?i; ?imkova, Ludmila; Li?ka, Alan; Bim, Daniel; Madridejos, Jenica M.L.; Pohl; Ruli?ek, Lubomir; Michl; Ludvik, Ji?i; Electrochimica Acta; vol. 321; (2019);,
Bromide – Wikipedia,
bromide – Wiktionary

2695-48-9, name is 8-Bromo-1-octene, 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. COA of Formula: C8H15Br

Schlenk flask was charged with 10·2BH3 (1.05 g, 3.62 mmol) and THF (15 mL), and cooled to -78 C. Then n-BuLi (2.5 M in hexanes, 6.4 mL, 16.0 mmol) was added with stirring. After 30min, Br(CH2)6CH=CH2 (2.80 g, 14.65 mmol) [S10] was added to the pale yellow solution over10 min. After 1 h, the cooling bath was removed. After 16 h, a 31P{1H} NMR spectrum showedthe consumption of 10·2BH3, and water (10 mL) was added. The aqueous phase was extractedwith Et2O (4 × 10 mL), and the combined organic layers dried (MgSO4) and filtered. The solventswere removed by rotary evaporation and the residue chromatographed (SiO2 column, 4 cm× 30 cm, hexanes). The solvent was removed from the product containing fractions by rotaryevaporation to give 11·2BH3 (0.476 g, 0.652 mmol, 18%) as a colorless oil.

The synthetic route of 2695-48-9 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Fiedler, Tobias; Barbasiewicz, Micha?; Stollenz, Michael; Gladysz, John A.; Beilstein Journal of Organic Chemistry; vol. 14; (2018); p. 2354 – 2365;,
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 13633-25-5 as follows. Recommanded Product: 1-Bromo-4-phenylbutane

General procedure: To a solution of 4a-4e (0.1 mmol) in dry DCM (5 mL) was addedDIPEA (0.17 mmol) in a Schlenk tube. The tube was screwed down,stirred and heated at 75 C for 10 min, and the reaction mixturewas cooled to room temperature and benzyl bromide (1.7 mmol)was added to the solution. The reaction mixture was stirred andheated at 75 C for 48 h. After cooling the mixture, silica gel wasadded to the crude mixture, the solvent was evaporated underreduced pressure and the residue was purified by flash chromatography with a mixture of hexanes/EtOAc/TEA (95:5:1).

According to the analysis of related databases, 13633-25-5, the application of this compound in the production field has become more and more popular.

Reference:
Article; Djigoue, Guy Bertrand; Kenmogne, Lucie Carolle; Roy, Jenny; Maltais, Rene; Poirier, Donald; Bioorganic and Medicinal Chemistry; vol. 23; 17; (2015); p. 5433 – 5451;,
Bromide – Wikipedia,
bromide – Wiktionary

Synthetic Route of 14922-91-9, The chemical industry reduces the impact on the environment during synthesis 14922-91-9, name is 5-Bromo-2-ethylaniline, I believe this compound will play a more active role in future production and life.

To a stirred mixture of 5-bromo-2-ethylaniline (3.39 g, 200 mmol) in distilled water (1 10 ml) is added concentrated sulfuric acid (5.60 ml), followed by brief heating at reflux until dissolution. The mixture is allowed to cool to room temperature, producing a fine precipitate, then further cooled to approximately 0 0C in an ice/salt bath. To this slurry is added an aqueous solution of sodium nitrite (1.17 g, 16.94 mmol) in distilled water (10 ml) dropwise over 15 minutes, maintaining a temperature below 5 0C, followed by additional stirring for 30 minutes. The reaction mixture is next filtered then added to a second solution of aqueous potassium iodide (8.44 g, 50.83 mmol) in distilled water (45 ml) dropwise at room temperature. After the addition is complete the solution is briefly heated to 80 0C then allowed to cool to room temperature again. The reaction mixture is extracted with ethyl acetate (3 x 50 ml), and the organic phase is washed with 1 M aqueous hydrochloric acid (30 ml) and aqueous sodium thiosulfate (2 x 30 ml). After drying over anhydrous magnesium sulfate and concentration in vacuo 4-bromo-1-ethyl-2-iodobenzene (4.90 g) is furnished as an orange liquid.

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, 5-Bromo-2-ethylaniline, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; SYNGENTA PARTICIPATIONS AG; SYNGENTA LIMITED; WO2009/150093; (2009); A1;,
Bromide – Wikipedia,
bromide – Wiktionary

Adding a certain compound to certain chemical reactions, such as: 174508-31-7, name is 5,7-Dibromo-2,3-dihydrothieno[3,4-b][1,4]dioxine, 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 174508-31-7, Computed Properties of C6H4Br2O2S

2,5-Bis(thieno[3,2-b]thiophen-2-yl)-2-3,4-ethylenedioxythiophene(TT-EDOT-TT).

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, 5,7-Dibromo-2,3-dihydrothieno[3,4-b][1,4]dioxine, other downstream synthetic routes, hurry up and to see.

Reference:
Article; Xue, Yu; Xue, Zexu; Zhang, Wenwen; Zhang, Wenna; Chen, Shuai; Lin, Kaiwen; Xu, Jingkun; Polymer; vol. 159; (2018); p. 150 – 156;,
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 4117-09-3 as follows. Computed Properties of C7H13Br

A clean, dry, 1 L 3-neck flask equipped with a stir bar and nitrogen inlet was charged with magnesium turnings (10.31 g, 0.4241 mol, 1.5 equiv.) and ?0.1 mg of iodine, and the flask was purged with nitrogen for 5 minutes. 750 mL of anhydrous THF [15 mL/g of 7-bromohept-1-ene (3)] was charged and stirring was initiated. 7-Bromohept-1-ene (3, 50.02 g, 0.2824 mol, 1.0 equiv.) was slowly added drop wise over 10-15 minutes under nitrogen. During this period, the pink color of iodine disappeared during initial stages, the reaction was found to be slightly exothermic, and the temperature of the contents was raised from an initial ambient (20-23 C.) to about 31 C. After the addition was complete, the resulting pale gray color solution was cooled to room temp (23 C.) and stirring was continued for an additional 2.5 h under nitrogen to form the Grignard reagent (7-hept-1-ene magnesium bromide). Into a separate 2 L dry three neck RB flask equipped with a mechanical stirrer, thermocouple and an addition funnel with nitrogen inlet, diethyl oxalate (4, 82.61 g 0.5642 mol, 2.0 equiv.) and 750 mL of anhydrous THF [15 mL/g of 7-bromo-1-pentene (3)] were charged under nitrogen. The mixture was cooled to below -20 C. temperature (Jacket temperature: -23 C.) with stirring. The Grignard reagent (7-hept-1-ene magnesium bromide), which was prepared as described above, was transferred using a cannula into a side-arm addition funnel set on top of the 2 L RB flask. The reagent was added drop wise slowly into diethyl oxalate-THF solution over 1 h 50 min, while maintaining the jacket temperature below -23 C. During the addition of the Grignard reagent, the reaction was found to be exothermic and the internal temperature was raised to maximum of -18 C. After the addition was complete, the mixture was warmed to -15 C., and the progress of the reaction was monitored by HPLC. After 3 h at -15 C., the reaction mixture was warmed to -10 C., quenched with 3N hydrochloric acid solution and the final pH was adjusted to 1.4-1.6 by drop wise addition. During the quench, the internal temperature rose to -6.7 C. due to an exotherm while, the jacket temperature was maintained at -12 C. The mixture was stirred for an additional 10 min and the pH was re-checked and confirmed to be approximately, 1.7-1.8. The mixture was warmed to 22 C., and the pH was again re-checked (pH=2.8) and re-adjusted to pH=1.2 with 3N hydrochloric acid solution. A total of 81 mL of 3N hydrochloric acid solution was used for quench and pH adjustment. Agitation was stopped and the layers allowed to settle. The organic phase was separated, and the bottom aqueous layer was back-extracted with dichloromethane (1*100 mL). The combined organic phases were concentrated on a rotary evaporator (Bath temperature: 45 C./Vacuum) to give the crude product as a yellow oil. The crude product was dissolved in 200 mL of dichloromethane (some solids/salts were present) and 200 mL water. The bottom aqueous phase was separated and back-extracted with dichloromethane (2*200 mL). The combined organic phases were dried over anhydrous magnesium sulfate (25 g), filtered and concentrated on a rotary evaporator (bath temperature: 45 C., under vacuum), to afford a pale yellow viscous as oil. The crude product was purified by flash chromatography in four equal portions, with each portion dissolved in about 25 mL of dichloromethane for loading onto a silica gel column and eluted using 5-10% ethyl acetate in hexanes. The selected fractions were combined and concentrated on a rotary evaporator (bath temperature: 45 C., under vacuum), and further dried under vacuum (<5 mm/Hg) at ambient temperature for 4 h to afford 36.49 g of ethyl 2-oxonon-8-enoate (5) in 65.2% yield as colorless oil. According to the analysis of related databases, 4117-09-3, the application of this compound in the production field has become more and more popular. Reference:
Patent; AbbVie Inc.; Abrahamson, Michael J.; Pruyne, Julie J.; Kielbus, Angelica B.; Lallaman, John E.; Reddy, Rajarathnam E.; Chemburkar, Sanjay R.; (29 pag.)US10059969; (2018); B1;,
Bromide – Wikipedia,
bromide – Wiktionary

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. 608-30-0, name is 2,6-Dibromoaniline belongs to bromides-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below. Computed Properties of C6H5Br2N

General procedure: A flask equipped with a septum and a stirring bar was charged with aniline derivative (2.00 g, 1.00 equiv). The flask was closed andTHF (5 mL) was added by using a syringe under an argon atmosphere.The solution was cooled to -20 C and BF3*OEt2(1.50 equiv) was added. Isoamyl nitrite (1.50 equiv) was then slowly added under vigorous stirring and the solution was stirred for 2 hat this temperature. The precipitate was filtered off and washed withice-cold Et2O. Without further isolation, the precipitate was then poured (with MeCN wash) into a freshly a prepared solution containing i-Pr2NH (3.00 equiv) in a mixture of THF-pyridine (9:1, 10 mL) at -20 C. The solution was stirred and allowed to warm slowly to r.t. for an additional 16 h. The reaction was then quenched with sat. NH4Cl solution, the aqueous phase was extracted twice with EtOAc and the organic layer was dried over MgSO4. The solvent was removed in vacuum and the crude product was purified by flash column chromatography (silica gel).

The synthetic route of 608-30-0 has been constantly updated, and we look forward to future research findings.

Reference:
Review; Hafner, Andreas; Hussal, Christoph; Braese, Stefan; Synthesis; vol. 46; 11; (2014); p. 1448 – 1454;,
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. 39478-78-9, name is 5-Bromo-2-methylaniline, A new synthetic method of this compound is introduced below., Product Details of 39478-78-9

5-bromo-2-methyl-4-nitroantine Two duplicate reactions were carried out in parallel: To a 3-necked 3 L flask was added H2SO4 (1.25 L). The flask was cooled to 0C. Then, 5-bromo-2-methylaniline (250 g, 1.34 mol) was added followed by the portion- wise addition of KNO3 (135.8 g, 1.34 mol). The solution was stirred at 20C for 3 hours. The crude reaction was then added to 10 L of ice water and a solid precipitated. The solid was filtered off to afford intermediate B.l, (5-bromo-2-methyl-4-nitroaniline after combining material from the duplicate reactions. The crude material was used directly for subsequent steps without additional 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 SHARP & DOHME CORP.; SIMOV, Vladimir; KAPLAN, William, P.; ACTON, John, J., III; ARDOLINO, Michael, J.; CHEN, Joanna, L.; FULLER, Peter, H.; GUNAYDIN, Hakan; LI, Derun; LIU, Ping; LOGAN, Kaitlyn Marie; METHOT, Joey; MORRIELLO, Gregori, J.; NEELAMKAVIL, Santhosh, F.; TORRES, Luis; YAN, Xin; ZHOU, Hua; (0 pag.)WO2020/92136; (2020); A1;,
Bromide – Wikipedia,
bromide – Wiktionary