Category: 52107-68-3

Related Products of 52107-68-3,Some common heterocyclic compound, 52107-68-3, name is 5-Iodo-2-methylbenzonitrile, molecular formula is C8H6IN, 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 dry flask under N2 atmosphere wasadded anhydrous diglyme (46 mL) and diisopropylamine (5.5 mL, 38.8 mmol). The solution was cooled to -78C in a dry ice bath, then n-butyllithium (2.5 M in hexanes, 5.53 mL) was added slowly. Benzonitrile intermediate 15 (2.4 g, 9.7 mmol) was dissolved in~3mL dry diglyme and added slowly dropwise to the reaction and was allowed to stir at -78C for 60 minutes. Ethyl-3,3-dimethyl acrylate (4.05 mL, 29.1 mmol) was added dropwise and allowed to stir an additional 1 hour at -78C. Concurrently, ZnI2 was generated in situ in a separate flame-dried flaskcontaining dry diglyme (15 mL). After addition of zinc powder (1.59 g, 24.3 mmol) to the flask, iodine (4.92 g, 19.4mmol) was added portionwise over 20 minutes to the reaction (warning:exothermic). The reaction vessel was warmed in 30 second bursts with a heat gun until the color of iodine was replaced with a metallic silver color. The suspension was allowed to cool to room temperature, then added to the first reaction mixture after its 2nd hour of stirring at -78C, and then allowed to slowly warm to room temperature over the course of 2 hours. The reaction was quenched with sat. aq. NH4Cl solution then extracted 3x with diethyl ether. The combined organic extract waswashed 3x with water and 1x with brine, then isolated, dried over MgSO4, vacuum filtered, and concentrated in vacuo. Purification via flash chromatography (0-15% EtOAc:hex) isolated 1.9 g of the desired product; a second flash chromatography purification of impure fractions resulted in an additional 400 mg to combine for 2.3 g of a light yellow solid (63% yield).

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

Reference:
Article; Yestrepsky, Bryan D.; Kretz, Colin A.; Xu, Yuanxi; Holmes, Autumn; Sun, Hongmin; Ginsburg, David; Larsen, Scott D.; Bioorganic and Medicinal Chemistry Letters; vol. 24; 6; (2014); p. 1538 – 1544;,
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com

Application of 52107-68-3, These common heterocyclic compound, 52107-68-3, name is 5-Iodo-2-methylbenzonitrile, 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.

A stirred slurry of sodium hydride (60% dispersion in mineral oil, 480 mg, 12.0 mmol) in DME (3.0 mL)was refluxed. 5-iodo-2-methylbenzonitrile (729 mg, 3.00 mmol), methyl benzoate (544 mg, 4.00 mmol),and DME (3.0 mL) were added to the slurry. After a catalytic amount of MeOH was added, the mixture was refluxed for 7 h. The mixture was cooled to 0C. water (10 mL) was added to quench the reactionand then 2 M HCl (10 mL) was added. The resulting mixture was diluted with EtOAc (30 mL). The aqueous layer was extracted with EtOAc (2×30 mL). The combined organic layers were washed with brine (10 mL), dried over Na2SO4, and filtered. The solvents were evaporated in vacuo. The crude product was purified by recrystallization from ethanol to give 5-iodo-2-(2-oxo-2-phenylethyl)benzonitrile (5g)(635 mg, 61%). Yellow white solid. Mp 134-136C. 1H NMR (400 MHz, CDCl3): delta = 7.98-8.04 (m, 3H),7.87-7.89 (m, 1H), 7.60-7.64 (m, 1H), 7.49-7.53 (m, 2H), 7.10-7.13 (m, 1H), 4.49 (s, 2H). 13C NMR (100MHz, CDCl3): delta = 194.7, 141.8, 140.8, 138.1, 136.0, 133.8, 132.6, 128.8, 128.3, 116.3, 115.6, 91.7, 43.2.IR (KBr): 3097, 3056, 3033, 2951, 2884, 2230, 1688, 1594, 1479, 1448, 1416, 1385, 1332, 1204, 1110,988, 906, 868, 837, 806, 752 cm-1. HRMS (EI): Calcd for C15H10INO 346.9807 (M)+, found 346.9820.

Statistics shows that 5-Iodo-2-methylbenzonitrile is playing an increasingly important role. we look forward to future research findings about 52107-68-3.

Reference:
Article; Yashiro, Kai; Sakata, Keito; Hachiya, Iwao; Shimizu, Makoto; Heterocycles; vol. 92; 11; (2016); p. 2032 – 2046;,
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com