Author: Jessica.F

Reference of 88-67-5,Some common heterocyclic compound, 88-67-5, name is 2-Iodobenzoic acid, molecular formula is C7H5IO2, 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: To a stirred solution of carboxylic acid (1.0 eq.) in ethanol (2 M) was added thionyl chloride (2.0 eq.) dropwise at room temperature, and then refluxed for 2 hours. After it was cooled to room temperature, the reaction mixture was concentrated under reduced pressure to give crude product, which was chromatographed on silica gel column using 1:30 (v/v) EtOAc-petroleum ether solution as eluent to afford isolated product esters in 80% – 95% yields. Esters (1.0 eq.) were added dropwise to a stirred solution of acetonitrile (2.0 eq.) and NaH (3.0 eq.) in THF (2 M) at room temperature, and then refluxed for 1h . After it was cooled to room temperature, Water was added dropwise to the reaction mixture under ice bath until no gas bubbles generated, and employing dilute hydrochloric acid neutralization to neutral, extracted with ethyl acetate, dried over magnesium sulfate and concentrated in vacuo to give crude product which was chromatographed on silica gel column using 1:4 to 1:2 (v/v) EtOAc-petroleum ether solution as eluent to afford isolated product beta-ketonitriles, white or light yellow solid compounds in 50% – 85% yields. Finally, stirred in concentrated sulfuric acid (3 M) at room temperature for 5 to 10 hours. The reaction mixture was neutralized to neutral by ammonia water, extracted with ethyl acetate, dried over magnesium sulfate and concentrated in vacuo to give crude product which was chromatographed on silica gel column using 1:1 to 2:1 (v/v) EtOAc-petroleum ether solution as eluent to afford isolated product beta-ketoamides 1a-p, white solid compounds in 45% – 85% yields.

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

Reference:
Article; Zheng, Congke; Zhang, Xiaohui; Ijaz Hussain, Muhammad; Huang, Mingming; Liu, Qing; Xiong, Yan; Zhu, Xiangming; Tetrahedron Letters; vol. 58; 6; (2017); p. 574 – 577;,
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com

Electric Literature of 181765-86-6,Some common heterocyclic compound, 181765-86-6, name is Methyl 5-bromo-2-iodobenzoate, molecular formula is C8H6BrIO2, 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 compound 10 (5.2 g, 0.015 mol) in dry CH2Cl2 (30 mL) was added DIBAL (30.5 mL, 1 M in THF, 30.5 mmol) at 0 C; The mixture was slowly warmed up to rt and stirred overnight. The mixture was then cooled to 0 C and quenched with citric acid (aq. 15%) slowly. The resulting mixture was extracted with CH2Cl2. The organic layer was washed with brine and dried with MgSO4. After removal of CH2Cl2 under vacuum, the resulting crude product was purified by silica column flash chromatography (hexanes/CH2Cl2, 1:1) to give compound 11 as a white solid (4.79 g, 0.0153 mol, 100%).

The synthetic route of 181765-86-6 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

Application of 289039-29-8,Some common heterocyclic compound, 289039-29-8, name is 2-Chloro-5-iodobenzonitrile, molecular formula is C7H3ClIN, 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.

Into a mixture of 2-chloro-5-iodobenzonitrile (1.32 g, 5 mmol), Pd(dba)2 (0.144 g, 0.25 mmol), and Qphos (0.178 g, 0.25 mmol) in THF (20 mL), (2-(tert-butoxy)-2- oxoethyl)zinc(II) chloride (1M in ether, 11 mL, 5.5 mmol) was added. The mixture was stirred at 70 C overnight. The reaction was then cool to rt, filtered through a Celite pad, and excess solvent was removed under reduced pressure. The reside was purified by silica gel column chromatography with AcOEt in hexane (0-20%) as eluent to afford tert-butyl 2-(4-chloro-3- cyanophenyl)acetate (0.8 g) as a brown oil.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 2-Chloro-5-iodobenzonitrile, its application will become more common.

Reference:
Patent; ACHILLION PHARMACEUTICALS, INC.; WILES, Jason, Allan; PHADKE, Avinash, S.; DESHPANDE, Milind; AGARWAL, Atul; CHEN, Dawei; GADHACHANDA, Venkat, Rao; HASHIMOTO, Akihiro; PAIS, Godwin; WANG, Qiuping; WANG, Xiangzhu; GREENLEE, William; (447 pag.)WO2017/35408; (2017); A1;,
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. 13329-40-3, name is 1-(4-Iodophenyl)ethanone belongs to iodides-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below. HPLC of Formula: C8H7IO

General procedure: Ketone (1 eq) and N-bromosuccinimide (NBS) (2 eq) were solved in acetonitrile and trimethylsilyl trifluoromethanesulfonate (TMS-OTf) (1 eq) was added. The reactions were stirred at T=40C until completeness, diluted with diethyl ether (2ml), washed with H2O (3×2ml), dried over Na2SO4 and concentrated under reduced pressure. This procedure provided bromoketones intermediates in 70-90% overall yield, with purities generally>90% as determined by HPLC-MS. The compounds were used without further purification.

The synthetic route of 13329-40-3 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Liessi, Nara; Cichero, Elena; Pesce, Emanuela; Arkel, Maria; Salis, Annalisa; Tomati, Valeria; Paccagnella, Matteo; Damonte, Gianluca; Tasso, Bruno; Galietta, Luis J.V.; Pedemonte, Nicoletta; Fossa, Paola; Millo, Enrico; European Journal of Medicinal Chemistry; vol. 144; (2018); p. 179 – 200;,
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. 61272-76-2, name is 4-Fluoro-2-iodoaniline, This compound has unique chemical properties. The synthetic route is as follows., Quality Control of 4-Fluoro-2-iodoaniline

Example 45 1-Butyl-4-(((5-fluoro-2-(triethylsilyl)-1H-indol-3-yl)methoxy)methyl)-N,N-dimethylcyclohexanamine (non-polar diastereomer) In a flask with a Schlenk attachment a mixture of Ain-08 (548 mg, 1.5 mmol), 4-fluoro-2-iodoaniline (426 mg, 1.8 mmol), [1,3-bis-(2,6-diisopropylphenyl)imidazol-2-ylidene]-3-(chloropyridyl)palladium(II) chloride (PEPPSI.(TM)., 204 mg, 0.3 mmol) and sodium carbonate (793 mg, 7.48 mmol) was evacuated for 30 min. N,N-Dimethyl formamide (8 ml), which had previously been saturated with argon for 1 h, was then added under an argon stream. The suspension was stirred overnight at 120° C. and then concentrated to small volume under vacuum. Toluene (3*30 ml) was repeatedly added to the residue, which was concentrated to small volume under vacuum again each time and taken up in water (20 ml) and ethyl acetate (20 ml). The phases were separated and the aqueous phase was extracted with ethyl acetate (2*20 ml). The combined organic phases were washed with 1 M sodium thiosulfate solution (30 ml) and saturated sodium chloride solution (50 ml) and concentrated to small volume under vacuum. The crude product (932 mg) was purified by flash chromatography (100 g, 3.6*25 cm) with ethyl acetate/methanol (9:1). Since no pure product could be isolated, the corresponding mixed fractions (472 mg) were purified by MPLC [130 g, LiChroprep Si60 (15-25 mum) 46*2.6 cm] with ethyl acetate/methanol (9:1). Yield: 343 mg (48percent), brown oil 1H-NMR (DMSO-d6): 0.82-0.98 (m, 18H); 1.05-1.55 (m, 13H); 1.65 (d, 2H, J=8.6 Hz); 2.10 (s, 6H); 3.24 (d, 2H, J=6.2 Hz); 4.55 (s, 2H); 6.92 (dt, 1H, J=9.1, 2.5 Hz); 7.26 (dd, 1H, J=2.5 and 10.0 Hz); 7.37 (dd, 1H, J=4.6 and 8.8 Hz); 10.76 (s, 1H). 13C-NMR (DMSO-d6): 3.0; 7.2; 13.9; 23.3; 24.0; 26.3; 30.6; 31.5; 36.6; 37.5; 55.6; 64.3; 75.1; 102.8 (d, J=22 Hz); 110 (d, J=26 Hz); 112.2; 121.5; 128.6 (d, J=10 Hz); 135.3; 135.8; 156.7 (d, J=232 Hz).

According to the analysis of related databases, 61272-76-2, the application of this compound in the production field has become more and more popular.

Reference:
Patent; GRUNENTHAL GMBH; US2009/215725; (2009); A1;,
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com

Reference of 887266-99-1, 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. 887266-99-1, name is 3-Fluoro-4-iodobenzonitrile belongs to iodides-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below.

General procedure: To a solution of ReIO2(PPh3)2 (10 mol %) in toluene (3 mL) were added the nitrile (1 mmol) and PhSiH3 (300 mol %). The reaction mixture was stirred at reflux temperature under air atmosphere and the progress of the reaction was monitored by TLC or 1H NMR. Upon completion, the reaction mixture was cooled to ambient temperature, stirred with charcoal during 3 min and then filtered through a plug of alumina/Celite. To the filtrate was added an ethereal solution of HCl (1.5 mol) to induce the precipitation of amine hydrochloride salts. The solids were isolated upon filtration and then washed with n-hexane to afford the pure amine hydrochloride salts, which are all known compounds.

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, 3-Fluoro-4-iodobenzonitrile, other downstream synthetic routes, hurry up and to see.

Reference:
Article; Cabrita, Ivania; Fernandes, Ana C.; Tetrahedron; vol. 67; 42; (2011); p. 8183 – 8186;,
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. 25245-29-8, name is 5-Iodo-1,2,3-trimethoxybenzene, A new synthetic method of this compound is introduced below., Recommanded Product: 5-Iodo-1,2,3-trimethoxybenzene

PREPARATION EXAMPLE 49 Synthesis of 2,6-dimethoxy-4-iodophenol To a solution of 5-iodo-1,2,3-trimethoxybenzene (3.2 g) in 1,2-dichloroethane (40 mL) was added aluminum chloride (1.6 g). The mixture was stirred at 60 C. for 4 hours and evaporated. The residue was dissolved in 1 M aqueous sodium hydroxide solution and washed with ether. The aqueous layer was then acidified and extracted with chloroform. The organic layer was washed with brine, dried over anhydrous magnesium sulfate and evaporated to give the title compound as white crystalline powder. Yield: 1.0 g (31%)

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; Kowa Co., Ltd.; US6867221; (2005); B2;,
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com

Adding a certain compound to certain chemical reactions, such as: 52570-33-9, name is Methyl 3-iodo-2-methylbenzoate, 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 52570-33-9, category: iodides-buliding-blocks

To a solution of methyl 3-iodo-2-methylbenzoate (10.0 g, 36.2 mmol) in carbon tetrachloride (200 mL) was added BS (8.4 g, 47.1 mmol) and benzoyl peroxide (4.4 g, 18.1 mmol), the suspension was heated at 90 C overnight. The mixture was then cooled to RT and filtered. The filtrate was concentrated to give the crude product, which was purified by silica-gel column (light petro 100%) to give methyl 2-(bromomethyl)-3- iodobenzoate (9.8 g, 76%) as a yellow solid.

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

Reference:
Patent; BIOTHERYX, INC.; MERCURIO, Frank; CHAN, Kyle, W.H.; SULLIVAN, Robert; ERDMAN, Paul, E.; FUNG, Leah; (105 pag.)WO2018/169777; (2018); A1;,
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com

Electric Literature of 355-43-1,Some common heterocyclic compound, 355-43-1, name is 1,1,1,2,2,3,3,4,4,5,5,6,6-Tridecafluoro-6-iodohexane, molecular formula is C6F13I, 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.

1.Tetramethyl hydrazine (1.0 mmol) was placed in a 25 mL round bottom flask at room temperature.2 mL of acetonitrile (water content 0.1%) solvent was injected, and then perfluoroiodohexane (1.1 eq) was added.The reaction was carried out under 36 W CFL light, and TLC was monitored until the reaction was complete (about 10 h).The obtained reaction product was poured into 100 mL of water, extracted three times with dichloromethane, and the organic phase was dried, and the organic solvent was evaporated under reduced pressure to give a crude product; 2.The crude product was subjected to silica gel column chromatography (silica gel needs to be pretreated with Et3N/PE=1:9 overnight), and eluted with an eluent (petroleum ether: ethyl acetate = 1:1 (V:V)). Eluent, distillation under reduced pressure,Obtained a white solid,It is the product N-[bis(dimethylamino)methylidene]-2,2,3,3,4,4,5,5,6,6,6-undecafluorohexanamide,The yield is 79%.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 1,1,1,2,2,3,3,4,4,5,5,6,6-Tridecafluoro-6-iodohexane, its application will become more common.

Reference:
Patent; Liaoning University; Liang Fushun; Wang Rui; Su Zhongmin; (13 pag.)CN109369467; (2019); A;,
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com

2401-21-0, name is 1,2-Dichloro-3-iodobenzene, belongs to iodides-buliding-blocks compound, is considered to be a conventional heterocyclic compound, which is widely used in drug synthesis. The chemical synthesis route is as follows. HPLC of Formula: C6H3Cl2I

EXAMPLE 48 5-Chloro-4-methoxy-2,2-dimethyl-2,3-dihydro-7-benzofurancarboxylic acid A mixture of methyl 4-methoxy-2,2-dimethyl-2,3-dihydro-7-benzofurancarboxylate, 7.1 g of pyridine, and 400 ml of tetrahydrofuran was cooled to -30° C. by means of an external dry ice/acetone bath. A solution of 27.5 g of iodobenzene dichloride in 100 ml of dry tetrahydrofuran was added dropwise to the mixture. After addition was complete, the reaction was stirred at room temperature overnight. The reaction mixture was concentrated in vacuo, water was added, and the mixture was steam distilled. To the residue were added ethyl acetate and diethyl ether. The organic mixture was washed with water, dried over sodium sulfate, and concentrated in vacuo.

The synthetic route of 2401-21-0 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Eli Lilly and Company; US4921982; (1990); A;,
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com