Related Products of 13421-00-6, A common heterocyclic compound, 13421-00-6, name is 5-Chloro-2-iodobenzoic acid, molecular formula is C7H4ClIO2, 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.
According to the procedure reported by Yu and co-workers [3], palladium acetate (22 mg, 0.10mmol), iodobenzene diacetate (644 mg, 2.0 mmol), iodine (507 mg, 2.0 mmol), and tetrabutylammonium iodine (739 mmol, 2.0 mmol) were added to a solution of 3-chlorobenzoic acid (313 mg, 2.0 mmol) in 1,2-dichloroethane (20 mL). The mixture was heated at 100 C with stirring for 2 h and then allowed to cool to room temperature. Iodobenzene diacetate (644 mg, 2.0 mmol) and iodine (507 mg, 2.0 mmol) were added to the mixture. After stirring at 100 C for 4 h, the resulting mixture was diluted with10% sodium carbonate. The aqueous layer was separated, washed with Et2O, and then acidified with 10% HCl. The resulting mixture was extracted with EtOAc and the organic layer was dried over Na2SO4; filtered; and concentrated under reduced pressure. The residue was purified by silica gel column chromatography (eluent: hexane/EtOAc = 4/1) to give crude 5-chloro-2-iodobenzoic acid (223 mg) as a colorless solid, which was suspended in thionyl chloride (2 mL). After stirring under reflux conditions for 2 h, the resulting mixture was concentrated under reduced pressure. The remaining thionyl chloride was removed by azeotropic distillation with benzene. The residue was dissolved in anhydrous CH2Cl2 (3 mL). To the mixture were added isopropylamine (56 mg, 0.95 mmol) and triethylamine (240 mg,2.37 mmol) at 0 C under a nitrogen atmosphere. After stirring at room temperature for 13 h, the resulting solution was diluted with EtOAc. The mixture was washed with 10% HCl, saturated aqueous NaHCO3, water, and brine; dried overNa2SO4; filtered; and concentrated under reduced pressure. The residue was purified by recrystallization from hexaneand CHCl3 to give 19 (138 mg, 21% in 3 steps) as colorless needles.
The synthetic route of 13421-00-6 has been constantly updated, and we look forward to future research findings.
Reference:
Article; Yakura, Takayuki; Fujiwara, Tomoya; Yamada, Akihiro; Nambu, Hisanori; Beilstein Journal of Organic Chemistry; vol. 14; (2018); p. 971 – 978;,
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com