Month: December 2020

These common heterocyclic compound, 5458-84-4, name is 1-Iodo-2-methoxy-4-nitrobenzene, 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. Computed Properties of C7H6INO3

2.00 g (7.17 mmol) of 2-iodo-5-nitroanisole, 2.02 g (14.3 mmol) of (2-fluoropyridin-3-yl)boronic acid (A. Bouillon, J.-C. Lancelot, V. Collot, P. R. Bovy, S. Rault, Tetrahedron 2002, 58, 3323-3328.), 1.81 g (21.5 mmol) of sodium hydrogen carbonate and 117 mg (0.14 mmol) of [1,1′-bis(diphenylphosphino)ferrocene]palladium dichloride are heated to 100 C. in a degassed mixture of 40 ml of dioxane and 10 ml of water for 1 h. After cooling, the mixture is diluted with water and extracted three times with ethyl acetate. The combined organic phases are dried over sodium sulfate, clarified over activated carbon and concentrated. Purification is effected by chromatography on silica gel (eluent: dichloromethane) to obtain 1.55 g (87% of theory) of the desired product. 1H NMR (400 MHz, DMSO-d6, delta/ppm): 3.32 (d, 1H), 8.02 (ddd, 1H), 7.95 (dd, 1H), 7.92 (d, 1H), 7.64 (d, 1H), 7.49 (ddd, 1H), 4.10 (s, 3H). HPLC (Method 6): Rt=3.61 min. MS (ESIpos, m/z): 249 (M+H)+.

The synthetic route of 1-Iodo-2-methoxy-4-nitrobenzene has been constantly updated, and we look forward to future research findings.

Reference:
Patent; BAYER SCHERING PHARMA ATIENGESELLSCHAFT; US2010/298293; (2010); A1;,
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. 2043-55-2, name is 1,1,1,2,2,3,3,4,4-Nonafluoro-6-iodohexane, A new synthetic method of this compound is introduced below., name: 1,1,1,2,2,3,3,4,4-Nonafluoro-6-iodohexane

(2) In another 4 liters of the pressure-resistant reactor, 750 g of perfluorobutylethyl iodide obtained in (1) was added, and the mixture was heated to 125 ¡ã C with stirring. A 3000 g solution of 5percent aqueous dimethylformamide was added to the reactor at a rate of 30 g/min using a metering pump. The temperature was controlled at 125-130 ¡ã C, the pressure was not higher than 1.2 MPa, and the reaction was continued for 30 hours.Remove the heat.The organic phase was separated by neutralizing with 1000 g of a 11.3percent aqueous potassium hydroxide solution.Wash once with 1000 g of deionized water, separate the organic phase, remove the light components,490 g of an intermediate product of 85percent of a fluorine-containing alcohol and 8percent of a fluorine-containing olefin were obtained.

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; Jinan Qifu New Materials Co., Ltd.; Shandong Chemical Institute; Li Haijing; Zhang Liting; (6 pag.)CN108911983; (2018); A;,
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com

Reference of 696-41-3,Some common heterocyclic compound, 696-41-3, name is 3-Iodobenzaldehyde, molecular formula is C7H5IO, 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: Synthesis of iodo-chrysin derivatives was accomplishedfollowing the general methods shown in Schemes 1 and 2.As outlined in Schemes 1 and 2, under anhydrous andanaerobic conditions, ZnCl2 (0.05 mol) was added to themixture of resorcinol (0.1 mol) and chloroacetonitrile (0.12mol) in diethyl ether (50 mL) cooled to 0C. The mixturewas reacted with anhydrous hydrogen chloride gas for 12hours. Intermediate compound 1, chrysin derivatives 2-5were synthesized according to Scheme 2. The Baker-VenKataraman reaction was employed in the synthesis ofchrysin derivatives [31]. 2, 4-dihydroxybenzoyl chloride (86mmol) was obtained after recrystallization with water. 2-Iodobenzaldehyde, 3-iodobenzaldehyde, 2-fluorine-5-iodobenzaldehyde or 3-iodo-4,5-dimethoxy benzaldehyde(12 mmol) and 10% NaOH (20 mL) were added to a solutionof compound 1 (10 mmol) in alcohol (5 mL). The mixturewas stirred at room temperature for 72 hours. Then the solutionwas acidified with 10% aqueous HCl to pH= 7 andstirred for another 48 hours at room temperature. The crudeproduce was purified by column chromatography (ethylacetate/ petroleum ether = 1:1) to get products, compound2: 7-hydroxy-2-(2-iodophenyl)-4H-chromen-4-one yielded62.7%, compound 3: 7-hydroxy-2-(3-iodophenyl)-4Hchromen-4-one yielded 61.5%, compound 4: 2- (2-fluoro-5-iodo- phenyl)-7-hydroxy-4H-chromen-4-one yielded 60.8%,compound 5:7-hydroxy-2-(3- iodo-4,5-di- methoxyphenyl)-4H-chromen-4-one yielded 62.3%. All compounds were yellowproducts.

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

Reference:
Article; Wei, Yun; Zheng, Qutong; Tang, Guotao; Song, Chen; Wang, Guan; Zhang, Yinxiang; Xiao, Yan; Zeng, Xianliang; Wang, Zongbao; Xiao, Jichang; Zheng, Xing; Medicinal Chemistry; vol. 12; 5; (2016); p. 441 – 447;,
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com

Adding a certain compound to certain chemical reactions, such as: 1829-28-3, name is Ethyl 2-iodobenzoate, 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 1829-28-3, Product Details of 1829-28-3

To a 2-dram vial with a PTFE-lined cap was charged with acetal 1d (29.4 mg, 0.101 mmol), ethyl 2-iodobenzoate (110 mg, 0.399 mmol), NBE-CO2Me (22.6 mg, 0.149 mmol), Pd(TFA)2 (3.3 mg, 0.00994 mmol), TFA-Gly-OH (3.3 mg, 0.0193 mmol), AgOAc (66.5 mg, 0.398 mmol), and DCE (2.00 mL). The resulting mixture was heated to 100¡ã C. and stirred for 24 h. After cooling to room temperature, ethylenediamine (0.100 mL) was added, and the resulting mixture was stirred at 23¡ã C. for 2 h. The mixture was filtered through a plug of silica gel, eluting with EtOAc (30 mL), and the filtrate was concentrated under reduced pressure. The residue was purified by flash column chromatography (4:1 hexanes/EtOAc eluent) to afford arylation product 3dp (30.8 mg, 69percent yield, Rf=0.33 in 2:1 hexanes/EtOAc) as a light yellow oil. 1H NMR: (400 MHz, CDCl3) delta 8.17 (d, J=8.5 Hz, 1H), 8.04 (s, 1H), 7.83 (d, J=8.1 Hz, 1H), 7.81-7.75 (m, 1H), 7.75-7.68 (m, 1H), 7.60-7.53 (m, 1H), 7.48 (td, J=7.5, 1.3 Hz, 1H), 7.41-7.33 (m, 2H), 7.27 (s, 1H), 7.19 (s, 1H), 7.05 (s, 1H), 6.32 (s, 1H), 5.40 (d, J=13.3 Hz, 1H), 5.23 (d, J=13.3 Hz, 1H), 4.95 (d, J=11.3 Hz, 1H), 4.85 (d, J=11.3 Hz, 1H), 4.05 (q, J=7.1 Hz, 2H), 2.36 (s, 3H), 0.96 (t, J=7.1 Hz, 3H). 13C NMR: (100 MHz, CDCl3) delta 169.2, 159.6, 148.6, 142.4, 141.5, 137.9, 137.5, 131.6, 131.2, 130.80, 130.78, 129.9, 129.7, 129.6, 129.1, 128.8, 128.1, 128.03, 128.01, 127.23, 127.21, 125.7, 103.6, 70.4, 70.1, 61.1, 21.5, 13.9. IR: (film) 1716, 1290, 1248, 1022, 761 cm?1. HRMS: (ESI+) m/z calc’d for (M+H)+ [C28H25NO4+H]+: 440.1856, found 440.1863.

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, Ethyl 2-iodobenzoate, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; The University of Georgia Research Foundation, Inc; Ferreira, Eric; Li, Qiankun; (47 pag.)US2018/65909; (2018); 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 34270-90-1 as follows. Quality Control of 1-Iodo-2-(2-iodoethoxy)ethane

A mixture of compound 1 (1 mmol), 1-iodo-2-(2-iodoethoxy)ethane (1 mmol) and anhydrouspotassium carbonate (140 mg, 1 mmol) in anhydrous acetonitrile (10 mL) was heated under reflux for1 h and then quenched with water (5 mL). Product 47 was extracted with ethyl acetate and purified ona chromatotron eluting with dichloromethane/methanol (8:2).Yield 66%; m.p. >200 C (decomp.); 1H-NMR (DMSO-d6): delta 8.55 (m, 1H), 8.46 (d, J = 5.2 Hz, 1H), 7.83(m, 1H), 7.10 (m, 2H), 4.13 (m, 4H), 3.98 (m, 4H), 3.74 (m, 4H), 3.67 (m, 4H). HR-MS (ESI). Calcd forC16H21N4O2 (M+): m/z 301.1665. Found: m/z 301.1650. Anal. Calcd for C16H21N4IO2: C, 44.87; H, 4.94;N, 13.08. Found: C, 44.97; H, 5.09; N, 12.69.

According to the analysis of related databases, 34270-90-1, the application of this compound in the production field has become more and more popular.

Reference:
Article; Strekowski, Lucjan; Saczewski, Jaros?aw; Raux, Elizabeth A.; Fernando, Nilmi T.; Klenc, Jeff; Paranjpe, Shirish; Raszkiewicz, Aldona; Blake, Ava L.; Ehalt, Adam J.; Barnes, Samuel; Baranowski, Timothy C.; Sullivan, Shannon M.; Sata?a, Grzegorz; Bojarski, Andrzej J.; Molecules; vol. 21; 4; (2016);,
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com

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. 355-43-1, name is 1,1,1,2,2,3,3,4,4,5,5,6,6-Tridecafluoro-6-iodohexane belongs to iodides-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below. name: 1,1,1,2,2,3,3,4,4,5,5,6,6-Tridecafluoro-6-iodohexane

General procedure: In a Pyrex glass tube were placed TTMSS (0.2 mmol), olefin (0.24 mmol), perfluoroalkyl iodide (0.24 mmol) and CH2Cl2 (5 mL). Then Na2S2O3 (0.5 mmol, 79 mg) and water (1 mL) were added to the mixture. After sealing the tube, the mixture was shaken and then irradiated with a Hg lamp at room temperature. After the reaction was completed, the mixture was extracted with CH2Cl2. The extract was washed with brine, dried over Na2SO4, filtered, and concentrated under reduced pressure. The resulting residue was purified by silica gel column chromatography to afford pure product. 4.2.4 Ethyl 2-methyl-3-perfluorohexylpropanoate (6a) Colorless oil. 1H NMR (400 MHz, CDCl3) delta 4.20 (q, J = 7.2 Hz, 2H), 2.90 (m, 1H), 2.73 (m, 1H), 2.09 (m, 1H), 1.30 (d, J = 7.6 Hz, 3H), 1.25 (t, J = 7.2 Hz, 3H); 13C NMR (150 MHz, CDCl3) delta 174.6, 61.1, 34.9 (t, JC-F = 21.1 Hz, C6F13C), 32.8, 18.3, 14.0; IR (KBr) 2962, 1735, 1240, 1219, 1146, 806, 697 cm-1; HRMS (ESI+) m/z calcd for C12H11F13O2Na [M+Na]+ 457.0450, found 457.0444.

The synthetic route of 355-43-1 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Yajima, Tomoko; Yamaguchi, Kanako; Hirokane, Rie; Nogami, Emiko; Journal of Fluorine Chemistry; vol. 150; (2013); p. 1 – 7;,
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com

Reference of 19821-80-8, 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. 19821-80-8 name is 1,3-Dibromo-2-iodobenzene, 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.

At -75 C butyllithium (14 mmol) in hexanes (5.6 mL) was added to a solution of 1,3-dibromo-2-iodobenzene (4.3 g, 12 mmol) in diethyl ether (0.18 L). After the solution was stirred for 2 h at -75 C, copper(II)chloride (9.7 g, 72 mmol) was added, and the reaction mixture was allowed to attain 25 C over a 12 h period. Cold water was added to the reaction mixture and the organic layer was separated. The aqueous phase was extracted with ethyl acetate (2¡Á0.10 L). The combined organic layers were dried over sodium sulfate before being evaporated. 2,2′,6,6′-tetrabromo-1,1′-biphenyl precipitates upon treatment of the residue with hexanes cooled to -20 C. The product is pure enough for further reaction; m.p. 214 – 215 C; 9.0 g (33%);1H NMR (CDCl3, 400 MHz): delta = 7.67 (d, J= 8.3 Hz, 4 H), 7.17 (t, J = 8.0 Hz, 2 H).

At the same time, in my other blogs, there are other synthetic methods of this type of compound, 1,3-Dibromo-2-iodobenzene, and friends who are interested can also refer to it.

Reference:
Patent; Lonza AG; EP1609795; (2005); A1;,
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com

Reference of 33348-34-4, A common heterocyclic compound, 33348-34-4, name is 4-Amino-3-iodobenzonitrile, molecular formula is C7H5IN2, 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.

Description for D20; delta-Cyano-IH-indole^-carboxylic acid (D20); A suspension of 4-amino-3-iodobenzonitrile (2.44 g), 2-oxopropanoic acid (2.64 g), DABCO (3.36 g), and Pd(OAc)2 in DMF (30 ml.) was heated to 105 0C and stirred at that temperature for 1 hour. The solvent was evaporated. EtOAc (200 ml.) was added and the resulting solution was washed with water (100 ml.) and aqueous NaOH solution (20 ml_). The combined aqueous solution was extracted with EtOAc (3 x 150 ml_). The organic fractions were combined. The combined solution was dried over anhydrous magnesium sulfate. The dried solution was concentrated. The residue was triturated to afford 5-cyano-1 /-/-indole-2-carboxylic acid (D20) (1.1 g) as a brown solid.

The synthetic route of 33348-34-4 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; GLAXO GROUP LIMITED; WO2009/153307; (2009); A1;,
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com

Electric Literature of 628-77-3, These common heterocyclic compound, 628-77-3, name is 1,5-Diiodopentane, 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.

Step 1: To a dry, nitrogen purged flask was charged with compound 2-1 (26.5 g, 0.1 mol,1.0 eq), compound 1-3 (17.8 g, 0.1 mol, 1.0 eq), potassium t-butoxide (13.4 g, 0.12 mol, 1.2 eq),anhydrous THF (450 ml).The mixture was stirred at 50 & lt; 0 & gt; C for 16 hrs.Add excess ammonium acetate, acetic acid.The mixture was refluxed for 16 hrs.After cooling to room temperature, the reaction solution was spin dried,and 600 ml of deionized water and 600 ml of ethyl acetatewere added to the residueand then stirred at 30 C for 30 mins.The organic phase was separated from the aqueous phasewhile the organic phase was washed three times with water (600 ml) and washed with saturated brine three times (600 ml).The organic phase wasdriedoveranhydrous sodium sulfate and filtered to dryness.The resulting crude product was purified by column chromatography usingethyl acetate / petroleum ether (1: 5 by volume) as a mobile phaseand vacuum dried at 50 C to give the first intermediate of the compound.The resulting intermediate intermediate 1-3 (37.9 g, 0.1 mol, 1.0 eq),compound 2-2 (71.3 g, 0.22 mol, 2.2 eq), potassium tert- 24.6 g, 0.22 mol, 2.2 eq), anhydrousTHF (250 mL).The mixture was stirred under nitrogen at 50 C for 16 hrs.After cooling to room temperature, thereaction solution was spin dried, and 600 ml of deionized water and 600 ml of ethyl acetate were added to the residue and thenstirredat 30 Cfor 30 mins.The organic phase was separated from the aqueous phase while the organic phase was washed three times with water (600 ml)and washedwith saturatedbrine three times (600 ml).The organic phase was dried over anhydrous sodium sulfate and filtered to dryness.Residue with ethylacetate / petroleum ether (volume ratio of 1: 6) as mobile phase The resultant crude product was purified by column chromatography at 50 deg.] Cto give compound 2-3 (35.4g after drying in vacuo to yield 79.02 %).

The synthetic route of 628-77-3 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Shanghai Hehui Optoelectric Co., Ltd.; Yan Liangliang; Gong Zhihao; Li Weimeng; (14 pag.)CN106939024; (2017); A;,
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com

Some common heterocyclic compound, 58313-23-8, name is Ethyl-3-iodobenzoate, molecular formula is C9H9IO2, 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. Safety of Ethyl-3-iodobenzoate

Ethyl 3-iodobenzoate (0.92 g, 3.34 mmol, 1 eq.), phenylboronic acid (0.87 g, 5.02 mmol, 1.5 eq.), palladium(II)acetate (37 mg, 0.167 mmol, 0.05 eq.) and sodium carbonate (706 mg, 6.66 mmol, 2 eq.) were dissolved in DMF (20 mL) at room temperature under nitrogen. The reaction was then heated at 80 C. for 1.5 hours. Worked up by adding ethyl acetate and rinsing 4 times with water. The organic layer was dried over sodium sulfate and stripped to give a dark oil. Purified over silica gel in 9:1 to 1:1 hexanes/ethyl acetate to obtain 3′-Amino-[1,1′-biphenyl]-3-carboxylic acid, ethyl ester (420 mg) as an oil. Yield=55%. LCMS detects (M+H)+=242.41.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 58313-23-8, its application will become more common.

Reference:
Patent; Carter, Percy H.; Cherney, Robert J.; Batt, Douglas G.; Duncia, John V.; Gardner, Daniel S.; Ko, Soo S.; Srivastava, Anurag S.; Yang, Michael G.; US2005/54627; (2005); A1;,
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com