Category: 689291-89-2

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. 689291-89-2, name is 5-Bromo-2-iodobenzaldehyde, A new synthetic method of this compound is introduced below., Quality Control of 5-Bromo-2-iodobenzaldehyde

General procedure: The 2-thioxo-4-thiazolidinone (1mmol), benzaldehydes (1 mmol) and NaOH (1.0 mmol) were added to ethanol withtotal volume of 15 mL. The reaction mixture was heated to reflux and stirredfor 2-24 h. After cooling to room temperature, the mixture was concentrated under reduced pressure, neutralized to pH 7.0 with dilute hydrochloric, and then extracted with ethyl acetate (3×100 mL). The combined organic extracts were washed with brine, dried over anhydrous Na2SO4, and concentrated. The resulting residue was recrystallization from ethanol.

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; Zhou, Li; Zhong, Ye; Xue, Meng-Zhu; Kuang, Dong; Cao, Xian-Wen; Zhao, Zhen-Jiang; Li, Hong-Lin; Xu, Yu-Fang; Wang, Rui; Chinese Chemical Letters; vol. 26; 1; (2015); p. 63 – 68;,
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com

Electric Literature of 689291-89-2, 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. 689291-89-2 name is 5-Bromo-2-iodobenzaldehyde, 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.

Example 15D N-[(1E)-(5-Bromo-2-iodophenyl)methylene]-N-(tert-butyl)amine The product from Example 15C (2.28 g, 7.3 mmol) in THF (10 mL) was treated with t-butylamine (1.61 g, 22.0 mmol) and stirred under nitrogen at room temperature for 40 hours. The mixture was concentrated under reduced pressure and the residue was dissolved in 30 mL of methylene chloride. The methylene chloride was washed with 10 mL water and concentrated to provide the title compound which was used in the next step without further purification. 1H NMR (CDCl3, 400 MHz) delta 8.29 (s, 1H), 8.05 (d, J=4 Hz, 1H), 7.66 (d, J=8 Hz, 1H), 7.19 (dd, J=4, 8 Hz, 1H), 1.34 (s, 9H). MS (DCl/NH3) 366 [M+H]+.

At the same time, in my other blogs, there are other synthetic methods of this type of compound, 5-Bromo-2-iodobenzaldehyde, and friends who are interested can also refer to it.

Reference:
Patent; Altenbach, Robert J.; Black, Lawrence A.; Chang, Sou-Jen; Cowart, Marlon D.; Faghih, Ramin; Gfesser, Gregory A.; Ku, Yi-Yin; Liu, Huaqing; Lukin, Kirill A.; Nersesian, Diana L.; Pu, Yu-ming; Curtis, Michael P.; US2005/272736; (2005); A1;,
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com

Adding a certain compound to certain chemical reactions, such as: 689291-89-2, name is 5-Bromo-2-iodobenzaldehyde, belongs to iodides-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 689291-89-2, COA of Formula: C7H4BrIO

(Z)-l,2-bis(5-bromo-2-iodophenyl)ethene (18a). A solution of phosphonium salt 16a (3.84 g, 6.02 mmol) in THF (60 mL) was cooled to 0 C in a 250 mL Schlenk flask under nitrogen with stirring. Potassium ‘butoxide (815 mg, 7.12 mmol) was added portionwise and the resulting mixture was held at 0 C for 30 min. A solution of benzaldehyde 17a (1.7 g, 5.5 mmol) in THF (60 mL) was added dropwise at 0 C and the reaction was allowed to warm up to room temperature and left stirring for 24 h. The reaction mix was partitioned between 1 : 1 water: diethyl ether. The aqueous layer was removed and extracted with diethyl ether (3x) and the organics were dried with MgS04, filtered and the solvent removed under reduced pressure to provide an off white solid that was further purified by a short plug (Si02: 10% ethyl acetate in hexane) to yield 2.95 g (4.99 mmol, 91%) 82:18 Z:E of 18a as an off-white solid that was used without further purification. -NMR (400 MHz, CDC13) delta: 7.70 (d, 2H, J= 8.4 Hz), 7.05 (dd, 2H, J= 8.4, 2.4 Hz), 7.02 (d, 2H, J= 2.4 Hz), 6.58 (s, 2H); HRMS (FAB) m/z calculated for Ci4H8Br2l2 Pv ]; 587.7082, found 587.7067.

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-iodobenzaldehyde, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; THE JOHNS HOPKINS UNIVERSITY; TOVAR, John Dayton; CARUSO, Jr., Anthony; WO2011/127383; (2011); A2;,
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com

Adding a certain compound to certain chemical reactions, such as: 689291-89-2, name is 5-Bromo-2-iodobenzaldehyde, belongs to iodides-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 689291-89-2, Quality Control of 5-Bromo-2-iodobenzaldehyde

Compound 12 (1.62 g, 5.20 mmol), triisopropylsilylacetylene (1.15 mL, 0.950 g, 5.20 mmol), PdCl2(PPh3)2 (46 mg, 0.065 mmol), and CuI (25 mg, 0.13 mmol) were added to Et3N (20 mL). The solution was bubbled with N2 at rt for 5 min and then stirred at rt and under N2 protection for 24 h. After the reaction was completed as checked by TLC analysis, the solvent was removed by rotary evaporation. The resulting residue was diluted with CHCl3. The mixture was filtered through a MgSO4 pad. The solution obtained was sequentially washed with HCl (aq 10%) and brine. The organic layer was dried over MgSO4 and concentrated under vacuum to give crude 23, which was further purified by silica flash column chromatography (hexanes/CH2Cl2, 4:1) to yield compound 23 (1.78 g, 4.87 mmol, 94%) as a colorless oil. IR (KBr) 2944, 2891, 2866, 2736, 2156, 1695, 1582, 1469, 1383 cm-1; 1H NMR (CDCl3, 500 MHz) delta 10.53 (s, 1H), 8.05 (d, J=2.0 Hz, 1H), 7.67 (dd, J=8.5, 1.5 Hz, 1H), 7.47 (d, J=8.0 Hz, 1H), 1.15 (s, 21H); 13C NMR (CDCl3, 125 MHz) delta 190.4, 137.5, 136.7, 135.4, 130.1, 125.9, 123.4, 101.1, 100.9, 18.8, 11.4; HRMS (CI) m/z calcd for C18H25BrOSi 364.0858, found 365.1071 [M+H]+.

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:
Article; Zhou, Ningzhang; Wang, Li; Thompson, David W.; Zhao, Yuming; Tetrahedron; vol. 67; 1; (2011); p. 125 – 143;,
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com

Some common heterocyclic compound, 689291-89-2, name is 5-Bromo-2-iodobenzaldehyde, molecular formula is C7H4BrIO, 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: 5-Bromo-2-iodobenzaldehyde

EXAMPLE 112b Preparation of intermediate 1-(2-iodo-5-bromo-phenyl)-3-trimethylsilyoxy-2-aza-1,3-butadiene To dry tetrahydrofuran (120 mL) was added a solution of LiHMDS (42 mmol, 42 ml) in THF under argon at room temperature, followed by the addition of 5-bromo-2-iodo-benzaldehyde (13 g, 42 mmol). After the mixture was stirred at room temperature for 0.5 h, trimethylsilyl chloride (5.32 mL, 42 mmol) was added dropwise. Then the temperature of the mixture was lowered to 0 C. on a cooling ice bath. To this mixture was added triethylamine (7.6 mL, 54.4 mmol) in one portion, followed by the dropwise addition of a solution of acetyl chloride (3.9 mL, 54.4 mmol) in diethyl ether (200 mL). The cooling bath was removed, and the mixture was stirred at room temperature for 1 h. The mixture was quickly filtered on celite under nitrogen, and filtrate was concentrated under reduced pressure to give the title compound as a yellow gum and used for the next step without further purification.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 689291-89-2, its application will become more common.

Reference:
Patent; Ding, Qingjie; Jiang, Nan; Yang, Song; Zhang, Jing; Zhang, Zhuming; US2009/156610; (2009); A1;,
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com

Electric Literature of 689291-89-2, A common heterocyclic compound, 689291-89-2, name is 5-Bromo-2-iodobenzaldehyde, molecular formula is C7H4BrIO, 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.

Compound 12 (32.0 mg, 0.103 mmol), 46 (55.6 mg, 0.103 mmol), PdCl2(PPh3)2 (3.6 mg, 0.0051 mmol), and CuI (1.96 mg, 0.0103 mmol) were added to Et3N (8 mL). The solution was bubbled with N2 at rt for 5 min and then stirred at rt under N2 protection for 8 h. After the reaction was completed as checked by TLC analysis, the solvent was removed by rotary evaporation. The resulting residue was diluted with CHCl3. The mixture was filtered through a MgSO4 pad. The solution obtained was sequentially washed with HCl (aq 10%) and brine. The organic layer was dried over MgSO4 and concentrated under vacuum to give crude 53, which was further purified by silica flash column chromatography (hexanes/CH2Cl2, 7:3) to yield compound 53 (21 mg, 0.029 mmol, 28%) as a white solid. Mp 75-76 C; IR (KBr) 2920, 2872, 2852, 2203, 1692, 1600, 1581, 1568, 1514, 1499, 1466, 1418 cm-1; 1H NMR (CDCl3, 500 MHz) delta 10.68 (s, 1H), 8.08 (d, J=1.5 Hz, 1H), 7.70 (dd, J=8.5, 1.5 Hz, 1H), 7.50 (d, J=8.5 Hz, 2H), 7.49 (d, J=8.5 Hz, 2H), 7.02 (s, 1H), 7.01 (s, 1H), 6.90 (d, J=8.5 Hz, 1H), 4.06-4.02 (m, 4H), 3.85 (s, 3H), 1.90-1.84 (m, 4H), 1.59-1.47 (m, 4H), 1.42-1.27 (m, 24H), 0.90-0.87 (m, 6H); 13C NMR (CDCl3, 125 MHz) delta 191.3, 160.2, 154.7, 153.8, 137.4, 137.0, 134.5, 133.5, 130.5, 126.4, 123.3, 117.1, 116.5, 116.3, 115.8, 114.4, 112.1, 96.2, 95.0, 89.7, 85.0, 70.2, 69.7, 55.7, 32.3, 30.1, 30.05, 30.01, 30.0, 29.9, 29.8, 29.76, 29.70, 26.5, 23.1, 14.5; HRMS (CI) m/z calcd for C44H55BrO4 726.3284, found 727.3430 [M+H]+.

The synthetic route of 689291-89-2 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Zhou, Ningzhang; Wang, Li; Thompson, David W.; Zhao, Yuming; Tetrahedron; vol. 67; 1; (2011); p. 125 – 143;,
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com

Application of 689291-89-2, 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 689291-89-2 as follows.

To a stirred solution of 5-bromo-2-iodobenzaldehyde (4.2 g, 13.5 mmol, 1 .0 equiv) in THF (20 ml_) was added t-butyl amine (4.26 ml_, 40.6 mmol, 3.0 equiv) at room temperature, under nitrogen atmosphere. The reaction mixture was stirred for 40 h at room temperature and evaporated under vacuum to obtain a residue. The residue was dissolved in DCM (100 ml_) washed with H20 (50 ml_), dried over sodium sulphate and evaporated to obtain (£)-/V-(5-bromo-2-iodobenzylidene)-2-methylpropan-2-amine (3.0 g, crude) as a yellow oily compound. 1H NMR (400 MHz, CDCI3) delta ppm 1 .32 (s, 9H), 7.20 (dd, J=2.8, 8.4 Hz, 1 H), 7.68 (d, J=8.4 Hz, 1 H), 8.07 (d, J=2.4 Hz, 1 H), 8.31 (s, 1 H).

According to the analysis of related databases, 689291-89-2, the application of this compound in the production field has become more and more popular.

Reference:
Patent; GLAXOSMITHKLINE INTELLECTUAL PROPERTY DEVELOPMENT LIMITED; AXTEN, Jeffrey; KETHIRI, Raghava Reddy; KRISTAM, Rajendra; VENKATESHAPPA, Chandregowda; (162 pag.)WO2018/15879; (2018); A1;,
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com

Electric Literature of 689291-89-2, 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. 689291-89-2, name is 5-Bromo-2-iodobenzaldehyde belongs to iodides-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below.

Step 2: (5-Bromo-2-iodo-benzyl)-ethyl-amine To 5-bromo-2-iodo-benzaldehyde (5.0 g, 16.1 mmol) in MeOH (20 mL) was added ethylamine (2M in MeOH; 16 mL, 24.0 mmol), followed by acetic acid (1.0 mL, 17.8 mmol), and the mixture was stirred at room temperature for 30 minutes. Sodium cyanoborohydride (2.0 g, 31.8 mmol) was then added over 5 minutes, and the reaction was stirred at room temperature over the weekend. The mixture was concentrated and partitioned between EtOAc and saturated aqueous NaHCO3. The aqueous layer was extracted with EtOAc, and the combined organic layers were dried over MgSO4, filtered, and concentrated. The residue was purified by silica gel chromatography (0-5% MeOH in CH2Cl2) to give the title compound.

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-iodobenzaldehyde, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; AMIRA PHARMACEUTICALS, INC.; US2009/197959; (2009); A1;,
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com

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 689291-89-2 as follows. Safety of 5-Bromo-2-iodobenzaldehyde

Intermediate 21; N-[(l£)-(5-bromo-2-iodophenyI)methylidene]-2-methyl-2- ropanamine; To a solution of 2-1, 4-Br benzaldehyde (2.0 g, 6.4 mmol) in anhydrous THF (10 mL) was added tert-butylamine (2.0 mL, 19.3 mmol) and the reaction stirred at room temperature under a nitrogen atmosphere for 4 days. The reaction was concentrated in vacuo and partitioned between dichloromethane and water. The organic layer was dried over anhydrous sodium sulfate and concentrated in vacuo to afford the desired compound as a pale yellow solid in quantitative yield.

According to the analysis of related databases, 689291-89-2, the application of this compound in the production field has become more and more popular.

Adding a certain compound to certain chemical reactions, such as: 689291-89-2, name is 5-Bromo-2-iodobenzaldehyde, belongs to iodides-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 689291-89-2, Quality Control of 5-Bromo-2-iodobenzaldehyde

To an ice-cold solution of 2,2,5, 5-tetramethyldihydrofuran-3-one (0.388g, 2.73mmoles) in anhydrous 1 ,2-diotamethoxyethane (5ml) is added sodium methoxide (0.177g, 3.27mmoles) in one portion. The reaction mixture is stirred for 5 minutes at this temperature, followed by the dropwise addition of 5-bromo-2-iodo-benzaldehyde (0.85Og, 2.73mmoles) as a solution in 1 ,2-dimethoxyethane (5ml). The reaction mixture is further stirred at O0C for 30 minutes, then at ambient temperature for a 1 hour. After partitioning between 1 M hydrochloric acid and dichloromethane, the organic phase is separated, and the aqueous phase is extracted again with additional dichloromethane. All organics are combined then concentrated in vacuo to afford 4-[1-(5-bromo-2-iodophenyl)methyliotadene]-2,2,5,5-tetramethyldihydrofuran-3-one(1.18g) as a yellow gum.

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; SYNGENTA LIMITED; SCUTT, James Nicholas; WO2010/136431; (2010); A1;,
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com