Category: iodides-buliding-blocks

Application of 263351-43-5, 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. 263351-43-5 name is tert-Butyl 3-iodobenzylcarbamate, 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 151: Synthesis of 4-Chloro-6-[3-(2-morpholin-4-yl-ethylamino)- benzylamino]-2H-phthalazin-l -one hydroformate; [3-(2-Morpholin-4-yl-ethylamino)-benzyl]-carbamic acid isopropyl ester; A mixture of (3-iodo-benzyl)-carbamic acid tert-butyl ester (272mg, 0.816mmol),4-(2-aminoethyl)morpholine (O.lbetamL, 1.225 mmol), K2CO3 (232mg, 1.679 mmol), CuI (19mg, 0.10 mmol), L-proline (19mg, 0.163mmol) and DMSO (5 mL) was heated at 85C for Ih. The reaction was cooled, poured onto water and the aqueous layer extracted with EtOAc (x3). The organic layers were combined and washed with water, brine and dried (Na2SO4). Chromatography (MeOH/EtOAc) afforded [3-(2-morpholin-4-yl- ethylamino)-benzyl]-carbamic acid isopropyl ester (200mg) as an orange viscous oil. m/z (M+l) 336.16.

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

Reference:
Patent; FOREST LABORATORIES HOLDINGS LIMITED; WO2008/61108; (2008); A2;,
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com

Application of 501433-06-3,Some common heterocyclic compound, 501433-06-3, name is 2,3-Difluoro-1,4-diiodobenzene, molecular formula is C6H2F2I2, 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.

Under nitrogen atmosphere, 2,3-difluoro-1,4-diiodobenzene (7, 430 mg, 1.18 mmol), bis-(triphenylphospino)dichloropalladium(II) (85.1 mg, 121 mumol) and copper(I) iodide (23.2 mg,122 mumol) were dissolved in anhydrous THF (20 mL) and triethylamine (20 mL).Trimethylsilylacetylene (0.41 mL, 2.96 mmol) was added and the solution stirred at 70 C for16 h. Subsequently, the reaction mixture was filtered through a bed of Celite, the solvent wasevaporated in vacuo and the crude product purified by column chromatography using silicaand n-hexane as eluent (Rf = 0.44) to obtain a colourless solid (332 mg, 1.08 mmol, 92%).Melting point: 78 C;1H NMR (500MHz, CDCl3, 300 K): delta = 7.12-7.10 (m, 2H) ppm;13C NMR (125 MHz, CDCl3, 300 K): delta = 151.4 (dd, 1JC,F = 255.9 Hz, 2JC,F = 15.0 Hz, 2C), 127.9 (mc,2C), 114.2 (mc, 2C), 103.7 (mc, 2C), 96.4 (mc, 2C), 0.1 (6C) ppm.IR (ATR): = 2960 (w), 2900 (w), 2165 (m), 1549 (w), 1489 (m), 1466 (s), 1310 (w), 1249 (s),1228 (m), 1170 (w), 1044 (m), 963 (s), 838 (vs), 817 (vs), 758 (vs), 702 (s) cm-1;MS (EI, 70 eV): m/z (%) = 306 (45) [M]+, 293 (100) [M-Me]+, 112 (41) [M-2I]+;HR-MS (EI, 70 eV): m/z = calcd. for C16H20F2Si2 [M]+ 306.1072, found 306.1072.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 2,3-Difluoro-1,4-diiodobenzene, its application will become more common.

Reference:
Article; Hamer, Sebastian; Roehricht, Fynn; Jakoby, Marius; Howard, Ian A.; Zhang, Xianghui; Naether, Christian; Herges, Rainer; Beilstein Journal of Organic Chemistry; vol. 15; (2019); p. 1331 – 1338;,
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com

Adding a certain compound to certain chemical reactions, such as: 51628-12-7, name is 2-(4-Iodophenyl)acetonitrile, 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 51628-12-7, name: 2-(4-Iodophenyl)acetonitrile

Preparation 10 4-(4-Iodophenyl)-tetrahydropyrane-4-carbonitrile. To a solution of (4-iodophenyl)-acetonitrile (2.43 g, 10.0 mmol) in DMSO (50 ml) was added sodium hydride (60% in oil, 1.2 g, 30 mmol) at room temperature. After stirring for 30 min., bis-2-chloroethyl ether (1.57 g, 11 mmol) was added. After stirring for a further 1 hr. at room temperature, the solution was poured into brine/water (1:1) and extracted twice with diethyl ether. The combined organic phases were dried over magnesium sulphate and concentrated in vacuo. The residue was purified by chromatography (15% ethyl acetate in petroleum ether), giving the title compound as a solid.

At the same time, in my other blogs, there are other synthetic methods of this type of compound, 2-(4-Iodophenyl)acetonitrile, and friends who are interested can also refer to it.

Reference:
Patent; LEO PHARMA A/S; US2012/101039; (2012); 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

These common heterocyclic compound, 2043-53-0, name is 1-Iodo-1H,1H,2H,2H-perfluorodecane, 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. COA of Formula: C10H4F17I

The catalyst was separated from the reaction liquid obtained in Example 5 by filtration, and the unreacted olefin was removed with an evaporator, giving 47.5 g of solid CF3(CF2)7CH2CH2I. A 200-ml SUS autoclave was charged with 47.5 g (0.082 mol) of the obtained solid CF3(CF2)7CH2CH2I, 9.9g (0.090 mol) of potassium acrylate, 25 g of t-butanol (solvent), 0.6 g of hydroquinone (polymerization inhibitor) and 0.01 g of hydroquinone monomethyl ether (polymerization inhibitor), and a reaction was then carried out with stirring at 180C for 6 hours.. As a result, CF3(CF2)7CH2CH2OCOCH=CH2 was obtained at a CF3(CF2)7CH2CH2I conversion rate of 99% and at a selectivity of 88%.. The results of NMR analysis revealed that polymerization of CF3(CF2)7CH2CH2OCOCH=CH2 was not detected.

The synthetic route of 1-Iodo-1H,1H,2H,2H-perfluorodecane has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Daikin Industries, Ltd.; EP1457477; (2004); A1;,
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com

Related Products of 33348-34-4, 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. 33348-34-4, name is 4-Amino-3-iodobenzonitrile, This compound has unique chemical properties. The synthetic route is as follows.

General procedure: In a flame-dried flask, AlMe3 (2 M in toluene, 1.11 mL, 2.18mmol, 1.2 equiv) was added to dry toluene (3.0 mL) under anitrogen atmosphere. The mixture was cooled to 0 C, and the2-iodoaniline (2.0 mmol, 1.1 equiv) in dry toluene (4.0 mL) was added. The mixture was stirred for a further 5 min at 0 C. Theice bath was removed, and the mixture was stirred for 20 min atroom temperature. The mixture was cooled to 0 C again, and cyclopentene carboxylate 2b (1.82 mmol, 1.0 equiv) in drytoluene (3.0 mL) was added dropwise over 2 min to the mixture. After stirring for 10 min at 0 C, the mixture was heated to 60 C, and stirring was continued for 16 h. After cooling to room temperature, HCl (1 M, 8.0 mL) was added. (Caution: gas evolution,exotherm.) The mixture was stirred for 15 min, then water (20 mL) and EtOAc (30 mL) were added. The mixture was extracted, the organic phase was separated, and the aqueous phase was re-extracted one more time with EtOAc (30 mL). Thecombined organic phases were washed with brine and dried (MgSO4). After filtration, the solvent was removed under reduced pressure, and the crude mixture was purified by column chromatography.

The chemical industry reduces the impact on the environment during synthesis 4-Amino-3-iodobenzonitrile. I believe this compound will play a more active role in future production and life.

Reference:
Article; Adeyemi, Ahmed; Wetzel, Alexander; Bergman, Joakim; Branalt, Jonas; Larhed, Mats; Synlett; vol. 30; 1; (2019); p. 82 – 88;,
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com

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. 626-44-8, name is 1,3,5-Triiodobenzene, A new synthetic method of this compound is introduced below., COA of Formula: C6H3I3

1,3,5-triiodobenzene (22.8 g, 0.05 mol) under nitrogen protection,Pd(dppf)Cl2.CH2Cl2 (2.0g, 0.0025mol) and CuI (10.0g, 0.052mol), isopropylamine (200ml) were added to tetrahydrofuran (500ml), sodium benzotriazole (22.5g, 0.16mol) The mixture was slowly added, and the mixture was heated to 80 ° C and stirred for 12 hours. TLC showed the end of the reaction, and a silica gel column (PE/EA = 2/1 to 1/1) afforded Compound 11 (15.6 g, yield 73percent).

The synthetic route of 626-44-8 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Shanghai Hehui Optoelectric Co., Ltd.; Wu Fan; (29 pag.)CN108623600; (2018); A;,
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com

Electric Literature of 135050-44-1, 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. 135050-44-1, name is 3-Chloro-4-iodoaniline, This compound has unique chemical properties. The synthetic route is as follows.

A mixture of 3-chloro-4-iodobenzenamine (500 mg, 1.97 mmol), 4- chlorophenylboronic acid (324 mg, 2.07 mmol), Na2CO3 (627 mg, 5.92 mmol) andPd(PPh3)4 (228 mg, 0.20 mmol) in 1,4-dioxane (21 mL) and H20 (4 mL) was stirred at80 C under argon for 16 h. The mixture was allowed to cool to RT and concentrated invacuo. The residue was purified by flash column chromatography on silica gel (ethyl acetate / petroleum ether = 5/1) to afford the desired product (424 mg, 91% yield) as a yellow solid.

The chemical industry reduces the impact on the environment during synthesis 3-Chloro-4-iodoaniline. I believe this compound will play a more active role in future production and life.

Reference:
Patent; ARAXES PHARMA LLC; JANES, Matthew, Robert; PATRICELLI, Matthew, Peter; LI, Liansheng; REN, Pingda; LIU, Yi; (397 pag.)WO2016/44772; (2016); A1;,
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com

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. 112671-42-8, name is 4-Bromo-1-iodo-2-nitrobenzene, This compound has unique chemical properties. The synthetic route is as follows., SDS of cas: 112671-42-8

Phenylboronic acid (76.84 g, 630.2 mmol) as starting material dissolved in 2780 mL THF was added to the round bottom flask, 4-bromo-1-iodo-2-nitrobenzene (309.96 g, 945.3 mmol), Pd(PPh3)4 (36.41 g,31.5 mmol), K2CO3 (261.3 g, 1890.6 mmol) and water 1390 mL were added and the resulting mixture was stirred at 80 C. When the reaction was completed, the resulting mixture was extracted with water and CH2Cl2 and the organic layer was dried over MgSO4 and concentrated to a silica gel column, and the resulting compound was recrystallized to obtain product was 122.68 g (yield: 70%).

According to the analysis of related databases, 112671-42-8, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Duksan Neolux Co., Ltd.; Park, Hyung Kun; Lee, Sun Hee; Lee, Yun Suk; So, Ki Ho; Park, Jong Kwang; Jung, Yeon Suk; Moon, Sung Yun; Lee, Jung Wook; (48 pag.)KR101614738; (2016); B1;,
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com

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. 101335-11-9, name is 2-Chloro-4-fluoro-1-iodobenzene, A new synthetic method of this compound is introduced below., name: 2-Chloro-4-fluoro-1-iodobenzene

Step I: 2-Chloro-4-fluoroiodobenzene (9.03g, 35.22mmol, 2.00eq), potassium hydroxide solution (4M, 22.01mL,5.00eq) and bis(triphenylphosphine)palladium dichloride (617.94mg, 880.50umol, 0.05eq) were added to a solution of11 (8.30g, 17.61mmol, 1.00eq) in 100mL dimethyltetrahydrofuran. The reaction solution was stirred at 70C undernitrogen atmosphere for 12 hours, then filtered through celite, and the filtrate was washed twice with 100mL brine. Theorganic phase was dried over anhydrous sodium sulfate, filtered and concentrated to give a crude product, which waspurified by silica gel column chromatography (PE:EA=40:1-10:1) to give the product 13 as a yellow solid (4.50g, 5.57mmol,yield 31.65%, purity 58.7%). MS [ESI, M+1]: 474.3.

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; Luoxin Biotechnology (Shanghai) Co., Ltd.; Shandong Luoxin Pharmaceutical Group Stock Co., Ltd.; LU, Jianyu; DING, Charles Z.; HU, Lihong; HE, Huijun; CHEN, Shuhui; DONG, Jiaqiang; WANG, Tie-lin; (124 pag.)EP3434668; (2019); A1;,
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com