Author: Jessica.F

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. 628-77-3, name is 1,5-Diiodopentane, This compound has unique chemical properties. The synthetic route is as follows., Quality Control of 1,5-Diiodopentane

Potassium carbonate (5.03 g, 36.44 mmol, 1.1 eq.) was added to a stirred solution of phenol (2) (14 g, 33.13 mmol, 1.0 eq.) and 1 ,5 diiodopentane (21.46 g, 9.86 mL, 66.26 mmol, 2.0 eq.) in DMF (250 mL). The solution was heated at 70C for 3.5h. The solution was poured into a mixture of ice/water (800 mL) and extracted with EtOAc (4 x 500 mL). The combined extracts were washed with H2O (2 x 250 mL), saturated brine (400 mL), dried (MgS04) and evaporated under reduced pressure to give a brown oil. Purification by flash column chromatography [n-heptane/EtOAc 40% to 80% in 10% increments] gave the product as a yellow foam (12.7 g, 85%). Analytical Data: LC/MS, RT 2.16 min; MS (ES+) m/z (relative intensity) 913 {[M + H]+, 100); 935 {[M + Na])+, 100).

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 628-77-3.

Reference:
Patent; MEDIMMUNE LIMITED; MASTERSON, Luke; VIJAYAKRISHNAN, Balakumar; CHRISTIE, Ronald, James; (118 pag.)WO2019/224340; (2019); A1;,
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com

Application of 5458-84-4,Some common heterocyclic compound, 5458-84-4, name is 1-Iodo-2-methoxy-4-nitrobenzene, molecular formula is C7H6INO3, 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.

To a solution of 1-iodo-2-methoxy-4-nitrobenzene (1.0 g, 3.6 mmol) in dichioromethane was added BBr3 solution (1 M, 10 mL) at -78 C. The solution stirred at that temperature for two hours and then warmed to room temperature overnight. Water was added at 0 C and the mixture was extracted with ethyl acetate, dried over Na2SO4 and concentrated in vacuo. The crude product was purified by flash chromatography on silica gel column with ethyl acetate-hexane (1:20), to give 2-iodo-5-nitrophenol as a yellow powder (300 mg, 3 1%). LCMS: m/z 263.8 [M-Hj.

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

Reference:
Patent; NOVOGEN LIMITED; EIFFE, Eleanor; HEATON, Andrew; GUNNING, Peter; TREUTLEIN, Herbert; ZENG, Jun; JAMES, Ian; DIXON, Ian; (172 pag.)WO2016/187667; (2016); 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. 105202-02-6, name is 2-Iodo-5-(trifluoromethyl)aniline, A new synthetic method of this compound is introduced below., name: 2-Iodo-5-(trifluoromethyl)aniline

3) To a solution containing a part (5.1 g) of 3-amino-4-iodebenzotrifluoride obtained in the preceding step, 16.75 g of dimethyldisulfide and 80 ml of chloroform, a solution having the rest (20.42 g) of 3-amino-4-iodebenzotrifluoride obtained in the preceding step dissolved in 20 ml of chloroform and 11.92 g of tert-butylnitrite, were simultaneously dropwise added at a temperature of from 25 to 30 C. After completion of the dropwise addition, the mixture was reacted at room temperature for 16 hours. After completion of the reaction, 200 ml of methylene chloride was added to the reaction mixture, and the mixture was washed with an aqueous hydrochloric acid solution with pH 1 to 2. Then, the methylene chloride layer was washed with water and dried over anhydrous sodium sulfate. Then, methylene chloride and chloroform were distilled off under reduced pressure. The obtained residue was purified by silica gel column chromatography to obtain 19.89 g of the desired product as an oily substance. The NMR spectrum data of this product are as follows. 1 H-NMR deltappm [Solvent: CDCl3 ] 2.51 (s,3H), 7.08 (dd,1H), 7.26 (d,1H), 7.90 (dd,1H)

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; Ishihara Sangyo Kaisha Ltd.; US5998334; (1999); A;,
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com

These common heterocyclic compound, 19099-54-8, name is 1-Iodo-2-isopropylbenzene, 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: C9H11I

Under a protective atmosphere of inert gas, Pd(OAc)2 (2.2 mg, 10 mol%), XPhos (19.1 mg, 20 mol%), NBE-CO2K (3.5 mg, were added to a 4.0 mL reaction flask equipped with a magnetic stir bar. 10 mol%), 2-iodoisopropylbenzene(0.2 mmol, 1.0 equiv.), ethylene oxide (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. Reaction vesselAfter cooling to room temperature, it was quenched with water (10 mL) EtOAc (EtOAc)concentrate. Purified by column chromatography, the eluent was petroleum ether to give 7-isopropyl-2,3-dihydrobenzofuran 25 mg (colorless oily liquid,Yield 77%).

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

Reference:
Patent; Wuhan University; Zhou Qianghui; Wu Chenggui; Cheng Honggang; (20 pag.)CN108329285; (2018); A;,
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. 181765-85-5, name is Methyl 4-chloro-2-iodobenzoate, This compound has unique chemical properties. The synthetic route is as follows., Product Details of 181765-85-5

General procedure: A seal-tube (15 mL) initially fitted with a septum containing anilide 1 (0.5 mmol), Pd(OAc)2 (11.3 mg, 0.050 mmol, 10 mol%), and AgOAc (83.5 mg, 0.50 mmol) was evacuated and purged with N2 three times. TFA (4.0 mL) and 2-iodobenzoate 5 (0.75 mmol) were added to the system and the reaction mixture was stirred at 120 C for 24 h. The reaction mixture was cooled to r.t. and filtered through a short Celite pad and washed with CH2Cl2 several times. The filtrate was concentrated by vacuum and purified on a silica gel column using hexane/EtOAc as eluent to give the corresponding pure phenanthridone product 6.

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 181765-85-5.

Reference:
Article; Gandeepan, Parthasarathy; Rajamalli, Pachaiyappan; Cheng, Chien-Hong; Synthesis; vol. 48; 12; (2016); p. 1872 – 1879;,
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com

Electric Literature of 612-55-5,Some common heterocyclic compound, 612-55-5, name is 2-Iodonaphthalene, molecular formula is C10H7I, 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

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

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

Related Products of 452-79-9, 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. 452-79-9 name is 2-Fluoro-1-iodo-4-methylbenzene, 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.

N-Bromosuccinimide (2.63g, 14.78mmol) and benzoylperoxide (0.20g, 0.62mmol) were added to a solution of 3-fluoro-4-iodotoluene (2.90g, 12.29mmol) in 7mL of tetrachloromethane. The resulting solution was refluxed for 20h. Thereafter, the reaction was allowed to cool to room temperature and was then diluted with 30mL of CH2Cl2. The solid phase was filtered off and the filtrate was washed with 30mL of a saturated solution of sodium thiosulphate. The organic layer was dried over Na2SO4 and evaporated. The crude product was purified by flash chromatography (AcOEt/PE 2:98), giving 3.45g (86%) of 8 as a white solid. Rf=0.76 (AcOEt/PE 5:95); mp=46-48C. 1H NMR (600MHz, CDCl3) delta 7.71 (m, 1H), 7.11 (m, 1H), 6.94 (m, 1H), 4.41 (s, 2H); 13C NMR (150MHz, CDCl3) delta 161.0 (J=246.5Hz), 140.6 (J=7.6Hz), 139.9 (J=1.3Hz), 126.4 (J=3.2Hz), 116.4 (J=24.5Hz), 81.3 (J=25.6Hz), 31.5; 19F (564MHz, CDCl3) delta -92.9 (t, J=7.3Hz). Anal. calcd for C7H5BrFI: C, 26.70; H, 1.60; found: C, 26.70; H, 1.58.

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

Reference:
Article; Castillo Melean, Johnny; Humpert, Sven; Ermert, Johannes; Coenen, Heinz H.; Journal of Fluorine Chemistry; vol. 178; (2015); p. 202 – 207;,
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com

Reference of 90434-01-8, 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 90434-01-8 as follows.

Example 8 N-[(R)-1-Hydroxymethyl-2-(1H-indol-3-yl)-ethyl]-2-isopropoxy-5-(3-ethylcarbamoylphenylethynyl)-benzamide 3-lodo-N-methyl-benzamide (58 mg), 5-Ethynyl-N-[(R)-1-hydroxymethyl-2-(1H-indol-3-yl)-ethyl]-2-isopropoxy-benzamide (100 mg), palladium dichlorobis(triphenylphosphine) (4.7 mg) and TBAF x 3 H2O (170 mg in THF (5 ml) were stirred at 80C for 5 hours. The reaction mixture was concentrated and extracted with ethylacetate / water. The combined organic layers were dried over sodium sulphate and the solvent was evaporated. The title compound was obtained in 79 % yield (89 mg) after flash chromatography. 1H-NMR (CDCl3): 8.48 (J = 7.3 Hz, 1H); 8.39 d (J = 2.0 Hz, 1H); 8.20 s (1H); 7.87 s (1H); 7.77 d (J = 6.6 Hz, 1H); 7.72 d (J = 7.6 Hz, 1H); 7.61 d (J = 6.6 Hz, 1H); 7.52 dd (J = 2.3 Hz / 8.6 Hz, 1H); 7.4 m (2 H); 7.19 m (1H); 7.09 m (2H); 6.90 d (J = 8.6 Hz, 1H); 4.66 m (1H); 4.57 m (1H); 3.81 m (2H); 3.14 m (2H); 3.03 d (J = 4.3 Hz, 3H); 1.27 m (3H); 1.21 m (3H).

According to the analysis of related databases, 90434-01-8, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Bayer Schering Pharma Aktiengesellschaft; EP1932831; (2008); A1;,
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com

Electric Literature of 461-17-6, 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. 461-17-6, name is 1,1,1-Trifluoro-4-iodobutane belongs to iodides-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below.

The alcohol of Example A2 (0.50 g, 1.38 mmol), tetrabutylammonium bromide (89 mg, 0.0.276 mmol), and KOH (232 mg, 4.14 mmol) were slurried in xylene (5.5 mL). Afterward, 1,1,1-trifluoro-4-iodobutane (0.98 g, 4.14 mmol) was added, and the resulting mixture was stirred in a sealed vial at 80 C. over the weekend. Subsequently, the mixture was filtered through celite and concentrated under N2. Chromatography (on silica, ethyl acetate/hexanes) afforded the ether in the form of a colorless oil (430.5 mg, 65.8% yield). NMR (CDCl3) delta 1.22-1.36 (m, 2H), 1.51 (s, 9H), 1.66-1.74 (m, 5H), 2.06-2.22 (m, 4H), 2.32 (d, 2H), 2.94 (t, 2H), 3.24 (d, 2H), 3.40 (t, 2H), 3.43 (t, 2H), 3.79 (d, 2H), 3.96 (dd, 2H). ESMS m/z=491.42 (M+NH4)+.

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, 1,1,1-Trifluoro-4-iodobutane, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; Barta, Thomas E.; Becker, Daniel P.; Bedell, Louis J.; Boehm, Terri L.; Brown, David L.; Carroll, Jeffery N.; Chen, Yiyuan; Fobian, Yvette M.; Freskos, John N.; Gasiecki, Alan F.; Grapperhaus, Margaret L.; Heintz, Robert M.; Hockerman, Susan L.; Kassab, Darren J.; Khanna, Ish K.; Kolodziej, Stephen A.; Massa, Mark A.; McDonald, Joseph J.; Mischke, Brent V.; Mischke, Deborah A.; Mullins, Patrick B.; Nagy, Mark A.; Norton, Monica B.; Rico, Joseph G.; Schmidt, Michelle A.; Stehle, Nathan W.; Talley, John J.; Vernier, William F.; Villamil, Clara I.; Wang, Lijuan J.; Wynn, Thomas A.; US2005/9838; (2005); A1;,
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com

Reference of 21740-00-1, 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 21740-00-1 as follows.

2-(2-r(T2i?.5i?V5-([(‘5-Fluoropyridin-2-v?oxylmethvU-2-methylpiperidin-l-yl)carbonyll-4- methylphenvUpyrimidine (E-5)The solution of D-9 (1 kg, 4.46 mol) was charged in a visually clean and dry 50 L flask equipped with a thermocouple and mechanical stirrer and was solvent switched to DCM (11.00 L). DIPEA (2 L, 1 1.45 mol) is added and then EA (1.22 kg, 5.67 mol) was added to this stirring solution. This solution was cooled with an ice bath (12 C). To this stirring solution was added T3P (7.87 L, 13.38 mol) through an addition funnel keeping the reaction temperature <21 0C over Ih. Once addition was completed, the reaction became yellow and heterogenous. To facilitate stirring 2L of DCM were added. The reaction was heated to 44 0C (small exotherm at 42C, which causes the temperature to rise to 46.7 C and maintain that temperature for 30 min). The reaction was aged at this temperature overnight. After 17 h the reaction was not complete and T3P (1.1 L, 1.870 mol) was added to accelerate conversion. The next day (42 h) the reaction was deemed complete by HPLC and was cooled in an ice bath to 4 C. 20 L of water was added (slowly for the first 1.5 L then pretty fast.) keeping the reaction temperature under 17 0C. This mixture was stirred at room temperature for 30 minutes. Then the mixture was transferred into a 50 L extractor charged with 20 L of MTBE. The flask was rinsed with an additional 2 L of water and 4 L of MTBE. The layers were cut and the organics are washed with 20 L IN NaOH and then 10 L of IN NaOH. Finally, the organics were washed twice with 10 L of brine 15%. The organic fractions (quantitative HPLC assay at 1.65 kg) are then treated with ~50w% of Darco KB (75Og) for 1.75 h, filtered on Solka floe and rinsed with 10 mL/g of MTBE (1.559 kg, 94.5% recovery). To a visually clean and dry 50 L RBF equipped with a mechanical stirrer, a thermocouple, a reflux condenser and a nitrogen inlet was charged the crude material from above (E-5 solution and all solvents used were filtered using a 1 mum in-line filter). The reaction mixture was solvent switched to IPAc and the final volume was adjusted to 7.5 L (about 4 mL/g of IPAc). The reaction mixture was warmed to 75 0C (all soluble), cooled to room temperature slowly and seeded at 45 0C with 18 g OfE1S (front run material, obtained from rex in IP Ac/heptane) stirred overnight (16 hr) at room temperature then heptane was added (6 ml/g) over 60 min. The reaction mixture was aged for 1 hr before to be cooled to 5 0C and stirred for 30 min. The suspension was then transferred onto a filter pot and rinsed with IPAC/heptane (2 x 3mL/g of cold 15% IPAc) and heptane (5 mL/g). The residual beige solid was dried under a flow of nitrogen for 18 hr (the product was found to be dry with < 0.3 wt% of solvents). 1.2 kg of E-5 was isolated as a light beige solid (99.4 LCAP, > 99.5 % ee, > 99.5 % dr, Pd level of 8 ppm and KF of 0.1). Data for E^: HRMS m/z (M+H): 421.2067, found. 421.2035, required.

According to the analysis of related databases, 21740-00-1, the application of this compound in the production field has become more and more popular.

Reference:
Patent; MERCK & CO., INC.; WO2008/147518; (2008); A1;,
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com