Category: iodides-buliding-blocks

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. 71838-16-9, name is 2-Bromo-1-iodo-4-methylbenzene, A new synthetic method of this compound is introduced below., name: 2-Bromo-1-iodo-4-methylbenzene

General procedure: To a stirred solution of o-bromoiodobenzene (1.3 ml, 10 mmol) in THF (10 ml) wasadded dropwise a solution of i-propylmagnesium chloride (2.0 M in THF, 5 ml, 10mmol) at -40 C. After 1 h, PCl3 (0.9 mL, 10 mmol) was added and stirred for 40 minat the same temperature. The mixture was then allowed to stand at room temperaturefor 12 h and cooled at -40 C again. A solution of proper arylmagnesium bromide (1.0M in THF, 22 ml, 22 mmol) was added dropwise. After 1 h, the resulting mixture wasthen stirred at room temperature overnight. Saturated aqueous solution of ammoniumchloride was added and the reaction mixture was extracted with Et2O three times. Thecombined organic layer was washed with water and brine and dried over magnesiumsulfate. The solvent was then evaporated in vacuo and the residue was purified bysilica gel column chromatography with hexane as eluent to afford the correspondingphosphines. After oxidation by H2O2 in acetone, the crude products were purified byusing flash chromatography with ethyl acetate as eluent, giving the pure products.Compounds 1d, 1e, 1f, 1l has been reported in our previous work.

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; Lin, Yan; Ma, Wei-Yang; Sun, Qiao-Ying; Cui, Yu-Ming; Xu, Li-Wen; Synlett; vol. 28; 12; (2017); p. 1432 – 1436;,
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. 26670-89-3, name is 2-Bromo-4-iodo-1-methylbenzene, This compound has unique chemical properties. The synthetic route is as follows., Recommanded Product: 2-Bromo-4-iodo-1-methylbenzene

7H-pyrrolo[2,3-d]pyrimidin-2-amine (134 mg, 1.00 mmol), 2-bromo-4-iodo-1-toluene (600 mg, 2.00 mmol),potassium carbonate (415 mg, 3.00 mmol) and proline (23 mg, 0.2 mmol) was added to the eggplant flask,dimethyl sulfoxide was added, and the reaction solution was deoxidized. Copper iodide (19 mg, 0.1 mmol) was added and the reaction solution was deoxygenated. Heat to 90 C and stir for 16 hours. After the reaction was completed, it was cooled to room temperature, water and ethyl acetate were added, and the mixture was filtered over celite. The target compound was obtained in an amount of 200 mg.

According to the analysis of related databases, 26670-89-3, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Chinese Academy Of Sciences Shanghai Pharmaceutical Institute; Zhao Yujun; Li Zhiqiang; Yan Ziqin; Li Jia; Zhou Yubo; Su Mingbo; Chen Zheng; (138 pag.)CN109810110; (2019); A;,
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com

Reference of 17533-08-3, 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. 17533-08-3 name is 1,2,4-Trifluoro-5-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.

To a stirred solution of 2,4,5-trifluoroiodobenzene (4) (1.50 g, 5.87 mmol), Pd(OAc)2 (26 mg, 2 mol %), triethylbenzylammonium chloride (1.32 g, 5.79 mmol), and NaHCO3 (0.98 g, 11.7 mmol) in 4 mL of DMF was added allyl alcohol (0.67 g, 0.79 mL, 11.6 mmol) under N2 atm. The resulting dark brown solution was heated at 45 C for 20 h. The reaction was quenched with saturated NH4Cl (10 mL) and extracted with EtOAc (3¡Á25 mL). The combined organic layers were dried over Na2SO4, filtered, and concentrated in vacuo. The crude product was purified by a silica gel column to give 5 (1.04 g; 95%). Light yellow liquid. (Rf: 0.2, 5:95 EtOAc/hexanes). GC/MS/MS (CI) (150 eV) m/z (rel intensity, %) 189.1 (M++1, 13), 144.9 (100). 1H NMR (400 MHz, CDCl3) delta=9.80 (br s, 1H, CHO), 7.04 (ddd, 1H, H-6′, JH,F=15.6, 8.4, 6.8 Hz), 6.88 (dt, 1H, H-3′, JH,F=10.0, 6.8 Hz), 2.92 (A2 part of A2X2 system, quasi t, 2H, 2¡ÁH-3, J=7.2 Hz), 2.78 (X2 part of A2X2 system, quasi t, 2H, 2¡ÁH-2, J=7.2 Hz). 13C NMR (100 MHz, CDCl3) delta=200.4 (C-1), 156.1 (ddd, C-2′, JC,F=242.7, 9.1, 2.6 Hz), 148.9 (ddd, C-4′, JC,F=248.4, 14.1, 12.4 Hz), 146.8 (ddd, C-5′, JC,F=243.4, 12.4, 3.7 Hz), 123.8 (ddd, C-1′, JC,F=18.1, 5.5, 4.3 Hz), 118.4 (dd, C-6′, JC,F=19.0, 5.7 Hz), 105.6 (dd, C-3′, JC,F=28.1, 20.6 Hz), 43.7 (C-2), 21.4 (C-3). IR (neat) 3065, 2934, 2829, 2725, 1725, 1632, 1522, 1425, 1388, 1333, 1211, 1152, 1099 cm-1.

At the same time, in my other blogs, there are other synthetic methods of this type of compound, 1,2,4-Trifluoro-5-iodobenzene, and friends who are interested can also refer to it.

Reference:
Article; Fistikci, Meryem; Gundogdu, Ozlem; Aktas, Derya; Secen, Hasan; Sahin, M. Fethi; Altundas, Ramazan; Kara, Yunus; Tetrahedron; vol. 68; 12; (2012); p. 2607 – 2610;,
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com

Reference of 202865-85-8, 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. 202865-85-8, name is 1-Bromo-4-iodo-2-methylbenzene belongs to iodides-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below.

A mixture of 10H-spiro[acridine-9,9?-fluorene] (1) (4.50 g,13.60 mmol), 1-bromo-4-iodo-2-methylbenzene (4.45 g, 15 mmol),copper iodide (260 mg, 0.1.36 mmol), (¡À)-trans-1,2-diaminocyclohexane(0.34 mL, 2.8 mmol) and sodium tert-butoxide (2.60 g,2.80 mmol) in 1,4-dioxane (15 mL) was refluxed overnight under a nitrogenatmosphere. The reaction mixture was then filtered through apad of silica and extracted with chlorofrom. The organic layer waswashed with water and brine, and dried over anhydrous sodium sulfate.The filtrate was concentrated in vacuo to give a crude mixture, which was purified by column chromatography (SiO2, CHCl3_hexane=1:4) toafford compound 3 (2.4 g, 54.5%) as a white solid.1H NMR (400 MHz, CDCl3) delta (ppm): 7.87 (d, J=8.3 Hz, 1H), 7.80(d, J=7.6 Hz, 2H), 7.43-7.32 (m, 5H), 7.28-7.18 (m, 3H), 6.97-6.89(m, 2H), 6.60-6.52 (m, 2H), 6.46-6.30 (m, 4H), 2.54 (s, 3H). 13C NMR(100 MHz, CDCl3) delta (ppm): 156.55, 141.22, 140.97, 140.20, 139.18,134.94, 133.41, 130.11, 128.35, 127.86, 127.58, 127.20, 125.73,124.77, 120.71, 119.89, 114.50, 56.72, 23.16.

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-Bromo-4-iodo-2-methylbenzene, other downstream synthetic routes, hurry up and to see.

Reference:
Article; Lee, Youngnam; Woo, Seung-Je; Kim, Jang-Joo; Hong, Jong-In; Dyes and Pigments; vol. 172; (2020);,
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. 21740-00-1, name is 5-Bromo-2-iodobenzoic acid, A new synthetic method of this compound is introduced below., COA of Formula: C7H4BrIO2

5-Bromo-2-iodobenzoic acid (409 mg, 1.25 mmol), A-(3-dimethylaminopropyl)-/V’- ethylcarbodiimide hydrochloride (288 mg, 1.5 mmol), 1 -hydroxybenzotri azole (135 mg, 1.0 mmol), AOY-diisopropyl ethyl amine (523 pL, 3.0 mmol), and benzyl amine (109 pL, 1.0 mmol) were dissolved in anhydrous DMF (5 mL) and stirred at room temperature for 16 hr. The reaction mixture was diluted with an excess of EtOAc and washed five times with water and brine. The organic layer was dried over Na2S04, filtered and concentrated. The residue was purified by flash column chromatography (EtOAc : DCM = 0 : 100 to 30 : 70) to give N- benzyl-5-bromo-2-iodobenzamide (361 mg, 87 %) as a white solid.

The synthetic route of 21740-00-1 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; DANA-FARBER CANCER INSTITUTE, INC.; GRAY, Nathanael S.; DE CLERCQ, Dries; JANG, Jaebong; JANNE, Pasi; TO, Ciric; ECK, Michael; PARK, Eunyoung; HEPPNER, David; (0 pag.)WO2019/164953; (2019); A1;,
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com

Electric Literature of 23399-70-4, These common heterocyclic compound, 23399-70-4, name is 5-Chloro-2-iodotoluene, 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.

Intermediate 6: 2:1 Mixture of 2-(bromomethyl)-4-chloro-1-iodobenzene and 1- bromo-2-(bromomethyl)-4-chlorobenzene; Lambda/-bromosuccinimide (6.34 g, 35.6 mmol) was weighed into a flask and carbon tetrachloride (200 ml) was added followed by 4-chloro-1-iodo-2-methylbenzene (8.57 g, 33.9 mmol, Fluorochem Ltd). The reaction mixture was stirred and dibenzoyl peroxide (0.822 g, 3.39 mmol) was added in one portion. The apparatus was then flushed three times with nitrogen and heated to reflux with vigorous stirring. After approximately 46 h at reflux, the reaction was allowed to cool to room temperature. The reaction mixture was filtered to remove the insoluble material and washed with aqueous sodium sulfite solution. The carbon tetrachloride layer was dried over sodium sulfate and evaporated to give a crude product as a pale yellow oil which crystallised on standing. The crude product was triturated with cyclohexane. The white insoluble material (1.30 g) was retained. The soluble material was then loaded onto 50 g silica SPE (pre-conditioned with cyclohexane) and was eluted with cyclohexane. Two product batches were obtained from this purification. The slower running material was obtained as a clear liquid which crystallised on standing to give the title compounds as a 2:1 mixture of 2- (bromomethyl)-4-chloro-1-iodobenzene and 1-bromo-2-(bromomethyl)-4- chlorobenzene (1.99 g).The faster running material (2.07 g) was combined with the triturated material (1.30 g) and was re-purified on 50 g silica SPE eluting with cyclohexane, exactly as before. A second batch of the title compounds, again as a 2:1 of 2-(bromomethyl)-4-chloro-1- iodobenzene and 1-bromo-2-(bromomethyl)-4-chlorobenzene (2.38 g) was obtained; LCMS: (System 2) tRET = 1 -37 min (no ions detected).

Statistics shows that 5-Chloro-2-iodotoluene is playing an increasingly important role. we look forward to future research findings about 23399-70-4.

Reference:
Patent; GLAXO GROUP LIMITED; COE, Diane, Mary; COOPER, Anthony, William, James; GORE, Paul, Martin; HOUSE, David; SENGER, Stefan; VILE, Sadie; WO2010/122088; (2010); A1;,
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com

Reference of 847685-01-2, The chemical industry reduces the impact on the environment during synthesis 847685-01-2, name is 4,5-Difluoro-2-iodoaniline, I believe this compound will play a more active role in future production and life.

General procedure: A mixture of the appropriate ortho-iodoaniline (5 mmol), pyruvic acid (1.04 mL, 15 mmol), DABCO (1.683 g, 15 mmol) and Pd(OAc)2 (56 mg, 0.25 mmol) in dry DMF (15 mL) was degassed 3 times and then was stirred at 105C for 16 h. The mixture was cooled to room temperature, neutralized with 10% aqueous hydrochloric acid and extracted with EtOAc (3?15 mL). The combined organic phases were washed with brine, dried over anhydrous Na2SO4, filtered and concentrated in vacuo. The crude product was purified by flash column chromatography using 95/5 EtOAc/MeOH and recrystallized from EtOH to yield the 1H-indole-2-carboxylic acid.

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, 4,5-Difluoro-2-iodoaniline, other downstream synthetic routes, hurry up and to see.

Reference:
Article; Kumar, Nag S.; Amandoron, Emily A.; Cherkasov, Artem; Brett Finlay; Gong, Huansheng; Jackson, Linda; Kaur, Sukhbir; Lian, Tian; Moreau, Anne; Labriere, Christophe; Reiner, Neil E.; See, Raymond H.; Strynadka, Natalie C.; Thorson, Lisa; Wong, Edwin W.Y.; Worrall, Liam; Zoraghi, Roya; Young, Robert N.; Bioorganic and Medicinal Chemistry; vol. 20; 24; (2012); p. 7069 – 7082;,
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com

Adding a certain compound to certain chemical reactions, such as: 19099-54-8, name is 1-Iodo-2-isopropylbenzene, 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 19099-54-8, COA of Formula: C9H11I

0.3 mmol of sodium carbonate and 0.1 mmol of 1,2-bis(4-methoxyphenyl)acetylene,Tetrakis(triphenylphosphine palladium) 0.005 mmol, bis(2-diphenylphosphinophenyl)ether 0.005 mmol,0.2 mmol of 4-(carboxylate)phenyl)boronic acid, 0.3 mmol of 2-isopropyliodobenzene, and 1 mL of N,N-dimethylformamide were added to a 15 mL reaction tube.Nitrogen was repeatedly filled 10 times, placed in an oil bath at 120 C, and reacted for 24 hours;Cooled to room temperature, the reaction was diluted with ethyl acetate, washed with water three times, the organic phase dried over anhydrous Na2SO4, filtered, and concentratedPurification by thin layer chromatography gave 29 mg of the desired product (yield: 59%).

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; Huaqiao University; Cheng Guolin; Lv Weiwei; (20 pag.)CN109879713; (2019); A;,
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. 5471-81-8, name is Methyl 4-iodo-3-methylbenzoate, A new synthetic method of this compound is introduced below., Recommanded Product: 5471-81-8

Under the protection of inert gas,Pd(OAc)2 (2.2 mg, 10 mol%), XPhos (19.1 mg, 20 mol%), NBE-CO2K (3.5 mg, 10 mol%) were added to a 4.0 mL reaction flask which was dried and equipped with a magnetic stir bar.Methyl 3-methyl-4-iodobenzoate (0.2 mmol, 1.0 equiv.),Phenyl glycidyl ether (0.6 mmol, 3.0 equiv.) and dry N-methylpyrrolidone (1.0 mL). The reaction flask was capped and stirred at room temperature for about 5 minutes, after which the mixture was heated to 80 C and stirred for 24 hours. After cooling the reaction vessel to room temperature, it was quenched with water (10 mL).Extracted with methyl tert-butyl ether (3 ¡Á 10 mL), dried with Na 2 SO 4Filter and concentrate under vacuum. Purified by column chromatography,The eluent is petroleum ether: ethyl acetate = 10:1 (v/v),49 mg of methyl 7-methyl-2-(phenoxymethyl)-2,3-dihydrobenzofuran-5-carboxylate (white solid, yield 82%).

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; Wuhan University; Zhou Qianghui; Wu Chenggui; Cheng Honggang; (20 pag.)CN108329285; (2018); A;,
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com

Application of 14452-30-3, A common heterocyclic compound, 14452-30-3, name is 1-(3-Iodophenyl)ethanone, molecular formula is C8H7IO, 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: A mixture of CuI (Sigma-Aldrich, 0.025 mmol, 5 mol%), anhydrousK3PO4 (0.65 mmol), 2-mercaptobenzimidazole (0.5mmol), DMSO (0.2 mL), and aryl halide (0.75 mmol) were addedto a reaction vial and a screw cap was fitted to it. The reactionmixture was stirred under air in a closed system at 100 C for24 h. The heterogeneous mixture was subsequently cooled toroom temperature and diluted with dichloromethane. The combinedorganic extracts were dried with anhydrous Na2SO4, andthe solvent was removed under reduced pressure. The crudeproduct was loaded into the column using minimal amounts ofdichloromethane and was purified by silica gel column chromatographyto afford the S-arylated product. The identity andpurity of products was confirmed by 1H NMR and 13C NMRspectroscopic analysis

The synthetic route of 14452-30-3 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Tan, Bryan Yong-Hao; Teo, Yong-Chua; Synlett; vol. 29; 15; (2018); p. 2056 – 2060;,
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com