Category: iodides-buliding-blocks

Application of 4897-68-1, A common heterocyclic compound, 4897-68-1, name is 1-Bromo-2-iodo-4-methoxybenzene, molecular formula is C7H6BrIO, 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: In an oven dried Schlenk tube under nitrogen atmosphere, were added allylic alcohol 6 (500.0mg, 1.76-3.38mmol), aryl halide 1 (2.11-4.06mmol), Pd(OAc)2 (11.8-22.7mg, 3mol%), triethylamine (356.2-684.1mg, 3.52-6.76mmol), followed by dry acetonitrile (4mL), at room temperature. The resulted reaction mixture was stirred for 24h at 80C. Progress of the reaction was monitored by TLC. The reaction mixture was quenched with the aqueous NH4Cl solution and extracted with ethyl acetate (3×20mL). The organic layer was dried over anhydrous Na2SO4 and concentrated under reduced pressure. Purification of the residue on a silica gel column chromatography using petroleum ether/ethyl acetate as eluent furnished the ketone 7 (46-58%).

The synthetic route of 4897-68-1 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Ramulu, B. Venkat; Mahendar; Krishna; Reddy, A. Gopi Krishna; Suchand; Satyanarayana; Tetrahedron; vol. 69; 38; (2013); p. 8305 – 8315;,
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com

Adding a certain compound to certain chemical reactions, such as: 20555-91-3, name is 1,2-Dichloro-4-iodobenzene, 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 20555-91-3, Safety of 1,2-Dichloro-4-iodobenzene

General procedure: Thiazolo[5,4-f]quinazolin-9(8H)-one 6 (0.341 mmol), CuI (0.065 g, 0.341 mmol, 1 equiv), and DBU (101 muL, 0.682 mmol, 2.0 equiv) in anhyd DMF (850 muL) were added to a 2 mL glass microwave vial. The mixture was stirred under microwave irradiation at 120 C for 10 min. Then Pd(OAc)2 (7.6 mg, 0.034 mmol, 10 mol%) and the appropriate aryl halide (0.682 mmol, 2.0 equiv) were added to the mixture. The reaction mixture was then stirred under microwave irradiation at 120 C for 5 h. The resulting solution was diluted with CH2Cl2, filtered through a cotton plug and washed with CH2Cl2 (50 mL). The crude product obtained by concentration of CH2Cl2 was purified by flash chromatography on silica gel with EtOAc/CH2Cl2 as eluent (1:0 to 1:1, v/v, for 7ah-j; 7:3 to 1:4, v/v for 7ba-j) to afford the corresponding product 7. N8-Benzyl-2-(3,4-dichlorophenyl)thiazolo[5,4-f]quinazolin-9(8H)-one (7ah) Prepared from 6a (0.100 g); yield: 0.095 g (64%); yellow solid; mp 242-245 C; Rf = 0.47 (CH2Cl2/EtOAc, 4:1, v/v). IR (neat): 3031, 1662, 1583, 1448, 1344, 1156, 830 cm-1. 1H NMR (CDCl3, 300 MHz): delta = 8.41 (d, J = 8.8 Hz, 1H, H4), 8.31 (d, J = 2.0 Hz, 1H, HAr), 8.25 (s, 1H, H7), 7.97 (dd, J = 8.4, 2.1Hz, 1H, HAr), 7.86 (d, J = 8.8 Hz, 1H, H5), 7.59 (d, J = 8.4 Hz, 1H, HAr), 7.46-7.30 (m, 5 H, HAr), 5.32 (s, 2 H, NCH2). 13C NMR (CDCl3, 75.4 MHz): delta = 168.9 (C), 160.0 (C), 153.4 (C), 147.0 (C), 146.1 (CH), 135.4 (C), 135.3 (C), 133.8 (C), 133.5 (C), 132.0 (C), 131.3 (CH), 129.4 (CH), 129.3 (2*CH), 129.2 (CH), 128.7 (CH), 128.4 (2*CH), 126.7 (CH), 126.6 (CH), 116.8 (C), 50.2 (CH2). HRMS (ESI+): m/z calcd for C22H14Cl2N3OS [M + H]+: 438.0235; found: 438.0234.

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, 1,2-Dichloro-4-iodobenzene, other downstream synthetic routes, hurry up and to see.

Reference:
Article; Couly, Florence; Dubouilh-Benard, Carole; Besson, Thierry; Fruit, Corinne; Synthesis; vol. 49; 20; (2017); p. 4615 – 4622;,
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. 31599-61-8, name is 4-Iodo-1,2-dimethylbenzene, This compound has unique chemical properties. The synthetic route is as follows., Recommanded Product: 31599-61-8

General procedure: Aryl thiourea (1, 0.5 mmol), aryl iodide (2, 0.6 mmol), CuSO4*5H2O (0.05 mmol), Cs2CO3 (2.0 equiv), 2,2?-bypyridine (0.05 mmol) were added in sealed tube equipped with a septum and magnetic stirring bar, H2O (2.0 mL) was then added. The mixture was stirred at 100 C and checked by TLC until the starting material was finished (about 3h). The reaction was terminated with sat. NH4Cl solution (3 mL) and then extracted with ethyl acetate. The crude solution was dried over anhydrous Na2SO4 and evaporated under vacuum. The residue was purified by flash column chromatography to afford the desired product 3a.

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 31599-61-8.

Reference:
Article; Liu, Xing; Zhu, Hui; Zhang, Shi-Bo; Cheng, Yu; Peng, Han-Ying; Dong, Zhi-Bing; Tetrahedron Letters; vol. 59; 33; (2018); p. 3165 – 3170;,
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com

Electric Literature of 452-82-4,Some common heterocyclic compound, 452-82-4, name is 1-Fluoro-2-iodo-4-methylbenzene, molecular formula is C7H6FI, 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.

9A. 4-Bromomethyl-1-fluoro-2-iodo-benzene 4-Fluoro-3-iodotoluene (50 g, 210 mMol), N-bromosuccinimide (37.7 g, 212 mMol) and 2,2′-azobis-(2-methylpropionitrile) (348 mg, 2.12 mMol) were dissolved in carbon tetrachloride (300 mL) under an atmosphere of dry N2. The mixture was heated to reflux for 4 hours and then cooled to ambient temperature. The mixture was concentrated under vacuum and triturated with Et2 O. The filtrate was successively washed with water, aqueous saturated NaHCO3 and brine. The ether layer was dried over MgSO4, filtered and concentrated under vacuum to give a red oil. The oil was chromatographed on flash silica gel eluding with hexanes to give 33.8 g of the titled compound as a white solid.

The synthetic route of 452-82-4 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Pfizer Inc.; US6150377; (2000); A;,
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com

Synthetic Route of 2142-70-3, These common heterocyclic compound, 2142-70-3, name is 1-(2-Iodophenyl)ethanone, 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.

[283] To a solution of 1-(2-iodophenyl)ethanone (4.0 g, 16.3 mmol) in a mixed solvent of chloroform (50 mL) and ethyl acetate (50 mL) was added cupric bromide (7.26 g, 32.5 mmol). The resulted mixture was stirred at reflux for 3h, then cooled down to roomtemperature, filtered, the filter cake was washed with ethyl acetate (50 mL), the filtrate was concentrated, the residue was purified by flash chromatography (petroleum ether: ethyl acetate= 50:1) to afford 2-bromo-1-(2-iodophenyl) ethanone (4.65 g, yield: 88%) as a light yellow oil.[284] ?H NIVIR (400 IVIFIz, CDC13-d): 7.98 (d, J = 8.0 Hz, 1H), 7.47 (d, J = 8.0 Hz, 2H), 7.19-7.21 (m, 1 H), 4.47 (s, 2H).

The synthetic route of 2142-70-3 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; SHANGHAI DE NOVO PHARMATECH CO.,LTD.; LI, Qun; GAO, Daxin; (158 pag.)WO2016/131380; (2016); A1;,
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com

Application of 887266-99-1,Some common heterocyclic compound, 887266-99-1, name is 3-Fluoro-4-iodobenzonitrile, molecular formula is C7H3FIN, 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: (4-Cyano-2-fluorophenyl)boronic acid 24.3 ml (48.6 mmol) of a 2 M solution of isopropylmagnesium chloride in diethyl ether were added dropwise to a solution of 10.0 g (40.5 mmol) of 3-fluoro-4-iodobenzonitrile in a mixture of 120 ml of anhydrous THF and 120 ml of anhydrous diethyl ether at -78 C. When the addition had ended, the mixture was stirred further at -78 C. for another 75 min. 15 ml (64.8 mmol) of triisopropyl borate were then added dropwise. The mixture was then stirred at -78 C. for a further 15 min, before the cold bath was removed and the reaction mixture was allowed to warm to RT. After 3 h at RT, 80 ml of 2 M hydrochloric acid were added and the mixture was stirred intensively at RT for 20 min. Thereafter, it was diluted with approx. 400 ml of water. The phases were separated and the aqueous phase was extracted three times with approx. 150 ml of ethyl acetate each time. The combined organic extracts were washed successively with water and saturated sodium chloride solution. After drying over anhydrous magnesium sulfate, the mixture was filtered and the filtrated was concentrated to dryness on a rotary evaporator. 3.68 g (55% of th.) of the title compound were obtained, this being employed for subsequent reactions without further purification. LC/MS (method F, ESIneg): Rt=0.53 min, m/z=164 [M-H]-.

The synthetic route of 887266-99-1 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; BAYER SCHERING PHARMA AKTIENGESELLSCHAFT; Haerter, Michael; Beck, Hartmut; Ellinghaus, Peter; Berhoerster, Kerstin; Greschat, Susanne; Thierauch, Karl-Heinz; Suessmeier, Frank; US2013/196964; (2013); A1;,
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com

Electric Literature of 25252-00-0, 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 25252-00-0 as follows.

Part C. 3′-(1-benzyl-6-cyano-1H-indol-3-ylmethyl)-4-carbamoyl-biphenyl-2-carboxylic acid benzyl ester:; 2-Bromo-5-iodobenzoic acid (6.54 g, 20.0 mmol) was dissolved in DMF (70 mL). Potassium bicarbonate (2.2 g, 22.0 mmol) was added, followed by benzyl bromide (2.8 mL, 22.0 mmol). The mixture was stirred at rt under N2 for 12 h. The reaction mixture was poured into water and extracted with EtOAc. The combined organic solution was washed with brine, dried over MgSO4, and concentrated and dried to give 9.05 g of the benzyl ester. The ester (2.3 g, 7.69 mmol), Zn(CN)2 (1.3 g, 11.5 mmol), and Pd[PPh3]4 were dissolved together in 25 mL of DMF. The mixture was de-gassed and heated at 90 C. for 4 h. Reaction mixture was concentrated and purified by chromatography (silica gel, 5% EtOAc in hexane) to give 1.8 g of the benzonitrile. MS: 316.0, 317.9 (M+1)+. The benzonitrile (1.4 g, 4.4 mmol) was dissolved in 15 mL of DMF. The reaction mixture was cooled at 0 C. Potassium carbonate (0.20 g, 1.45 mmol) was added, followed by dropwise addition of 30% hydrogen peroxide solution (1.2 mL). The cooling bath was removed and the mixture was stirred at rt for 12 h. The reaction was quenched with aqueous NaHSO3 and water. The formed precipitate was filtered and dried to give 1.1 g of the desired amide. MS: 334.2, 336.3 (M+1)+. A mixture of the resulting amide (0.2 g, 0.6 mmole), bis(pinacolato)diboron (0.228 g, 0.9 mmol) and anhydrous KOAc (0.18 g, 1.8 mmol) in 2 mL of 1,4-dioxane was purged with argon, then (1,1′)-bis(diphenylphosphino)ferrocene)palladium(II) chloride (20 mg, 0.024 mmol) was added. The resulting mixture was heated in a sealed tube in a microwave reactor at 100 C. for 2 h then left standing overnight at rt. The reaction was diluted with water and extracted 3× with EtOAc. The combined extracts were washed with brine, dried over Na2SO4, filtered and evaporated in vacuo. Chromatography on silica gel (hexane/ethyl acetate 1:1) provided the boronate (0.13 g, 57%). A mixture of this compound, the compound of Part B (0.1 g, 0.25 mmol), and K3PO4 (0.11 g, 0.5 mmol) in 5 mL dioxane was degassed and then treated with tetrakis(triphenylphosphine)palladium(20 mg, 0.017 mmol). The resulting mixture was heated in a 95-100 C. oil bath under N2 for 2 h, then stirred at rt overnight. The reaction mixture was diluted with brine and extracted 3× with EtOAc. The combined extracts were washed with brine then dried over anhydrous Na2CO3, filtered and evaporated. Chromatography on silica gel (hexane/ethyl acetate 1:1) provided the product (0.12 g, 83%) as a light yellow foam. 1H NMR (400 MHz, CDCl3) delta ppm 4.07 (s, 2H) 4.90 (s, 2H) 5.23 (s, 2H) 6.91 (d, J=6.15 Hz, 2H) 7.05 (m, 3H) 7.20 (m, 6H) 7.29 (m, 5H) 7.42 (d, J=7.91 Hz, 1H) 7.51 (d, J=10.99 Hz, 2H) 7.98 (dd, J=8.13, 1.98 Hz, 1H) 8.19 (d, J=2.20 Hz, 1H). LC/MS m/z 576.16 (M+H)+.

According to the analysis of related databases, 25252-00-0, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Smallheer, Joanne M.; Corte, James R.; US2005/228000; (2005); A1;,
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com

6414-69-3, Adding some certain compound to certain chemical reactions, such as: 6414-69-3, name is Ethyl 3-iodopropanoate, 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 6414-69-3.

EXAMPLE VI Ethyl 2-Carboethoxy-3-indolepropanoate Ethyl 2-indolecarboxylate (3 gm), ethyl 3-iodopropanoate (5.4 gm), potassium carbonate (5 gm), and acetonitrile (50 ml) were combined and the mixture heated to reflux for 48 hours. The mixture was cooled and poured into water (50 ml). The mixture was extracted with ether (3*75 ml) and the combined ether extracts were washed with water (3*30 ml). The organic layer was dried over sodium sulfate and the solvent removed on a rotary evaporator. The diester product was obtained as a colorless oil.

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 6414-69-3.

Reference:
Patent; C.D. Searle & Co.; US5137910; (1992); A;,
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com

Adding a certain compound to certain chemical reactions, such as: 755027-18-0, name is 1-Bromo-4-iodo-2-methoxybenzene, 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 755027-18-0, HPLC of Formula: C7H6BrIO

To a solution of l-bromo-4-iodo-2-methoxybenzene (L. A. Hasvold et al., US 2004/0254159, EXAMPLE 57B) (33.45 g, 107 mmol) in MeCN (100 mL) was added acrylic acid (9.61 g, 133 mmol), Et3N (37.2 mL, 267 mmol) and palladium acetate (719 mg, 3.2 mmol). The reaction mixture was heated to 90C for 40 minutes, cooled to RT and poured into 2.4-L 1 M HCl. After stirring for 30 minutes, the solid was filtered, suspended in EtOH (230 mL) heated to reflux and allowed to cool to RT with stirring overnight. The solid was filtered and washed with 1 : 1 EtOH hexane (50 mL) to give the title compound. LRMS ESI+ (M+H)+ 257.0.

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; MERCK & CO., INC.; WO2008/57208; (2008); A2;,
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. 20691-72-9, name is 4-Iodo-2-nitroaniline, A new synthetic method of this compound is introduced below., HPLC of Formula: C6H5IN2O2

Commercial 4-iodo-2-nitroaniline was reduced with 5 eq tin dichloride dihydrate in ethanol solution (75 C., 2 h) to give 92% 4-iodo-1,2-phenylenediamine as light red solid.

The synthetic route of 20691-72-9 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; UNIVERSITAET DES SAARLANDES; US2012/46307; (2012); A1;,
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com