Category: 289039-29-8

Adding a certain compound to certain chemical reactions, such as: 289039-29-8, name is 2-Chloro-5-iodobenzonitrile, 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 289039-29-8, Safety of 2-Chloro-5-iodobenzonitrile

A. 2-Chloro-5-iodo-benzaldehyde. To a 0 C. solution of 2-chloro-5-iodo-benzonitrile (10.6 g, 40.4 mmol) in toluene (100 mL) was added DiBAL-H (1.5 M in toluene; 40.4 mL, 60.6 mmol). The mixture was stirred at 0 C. for 15 min and then warmed to rt for 3 h. The mixture was poured over 1.0 M H2SO4 (10 mL), MeOH (100 mL), and ice. The mixture was stirred vigorously and then was extracted with EtOAc (200 mL). The organic layer was dried and concentrated to give the title compound (2.98 g, 31%). 1H NMR (CDCl3): 10.37 (s, 1H), 8.22 (d, J=2.2, 1H), 7.83 (dd, J=8.4, 2.2, 1H), 7.21 (d, J=8.4, 1H).

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

Reference:
Patent; Ameriks, Michael K.; Axe, Frank U.; Edwards, James P.; Grice, Cheryl A.; Cai, Hui; Gleason, Elizabeth Ann; Meduna, Steven P.; Tays, Kevin L.; Wiener, John J. M.; Wickboldt, Alvah T.; US2008/200454; (2008); A1;,
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 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 289039-29-8 as follows. Product Details of 289039-29-8

2-chloro-5-iodo-benzamidine 374.8 mL (374.8 mmol) lithium bis-trimethylsilylamide (1 M in hexane) are placed in 300 mL diethyl ether and combined with 50.0 g (189.8 mmol) 2-chloro-5-iodobenzonitrile. The reaction mixture is stirred for 1.5 hours at ambient temperature under an argon atmosphere and then cooled to 0 C. Then 5 molar hydrochloric acid is slowly added. The precipitate thus formed is suction filtered and dried. Yield: 56.0 g

According to the analysis of related databases, 289039-29-8, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Brandl, Trixi; Maier, Udo; Hoffmann, Matthias; Scheuerer, Stefan; Joergensen, Anne T.; Pautsch, Alexander; Breitfelder, Steffen; Grauert, Matthias; Hoenke, Christoph; Erb, Klaus; Pieper, Michael; Pragst, Ingo; US2007/244104; (2007); A1;,
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com

289039-29-8, 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. 289039-29-8, name is 2-Chloro-5-iodobenzonitrile, This compound has unique chemical properties. The synthetic route is as follows.

In a sealed tube, a mixture of 2-chloro-5-iodobenonitrile 111-5 (1.30 g, 5 mmol), 0.5 M (2-tert-butoxy-2-oxoethyl) zinc(II) chloride 111-6 in ether (11 mL, 5.5 mmol), Pd(dba)2 (144 mg, 0.25 mmol), Q-phos (178 mg, 0.25 mmol), and THF (20 mL) under argon was stirred at 70 C for 18 hours. After cooling to room temperature, the solvents were evaporated and the residue was redissolved in ethyl acetate, washed with water and brine, dried over Na2SO4 and concentrated to dryness by rotary evaporation. The crude product was purified by silica gel flash chromatography, eluted with 30% ethyl acetate in hexane to give tert-butyl 2- (4-chloro-3-cyanophenyl)acetate 111-7 as a brown oil. MS m/z 252.1 (M + 1).

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; IRM LLC; CHENG, Dai; ZHANG, Guobao; HAN, Dong; GAO, Wenqi; PAN, Shifeng; WO2010/101849; (2010); A1;,
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com