These common heterocyclic compound, 17564-64-6, name is 2-(Chloromethyl)isoindoline-1,3-dione, 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. Computed Properties of C9H6ClNO2
The N,Se acetal 5 was prepared by a slight and safer modification of the original procedure4 where, the required phenylselenol intermediate was replaced by sodium phenylselenolate. In a 50 mL three-neck flask equipped with a reflux condenser were placed diphenyl diselenide (0.63 g, 2 mmol) and 16 mL of dry DMF. The solution was heated at 60 C and stirred rapidly under nitrogen while NaBH4 (0.15 g, 4 mmol) was added portionwise. Hydrogen was evolved and the reaction mixture turned colorless and homogeneous upon complete reduction of the selenide. The reaction was heated at 110 C for 1 h and then cooled to room temperature. Solid N-chloromethylphthalimide (0.78 g, 4 mmol) was added to the orange solution. After stirring at room temperature for 12 h, 2 N aqueous hydrochloric acid (10 mL) was added carefully to the white suspension. The entire product mixture was poured into 50 mL of water and 40 mL of diethyl ether, mixed, and separated. The aqueous phase was extracted with 20 mL of diethyl ether and the combined organic phases were washed with H2O (4 ¡Á 10 mL), 10 mL of brine, dried over sodium sulfate and concentrated. The solid residue was washed with light petroleum (2 ¡Á 10 mL) and dried over P2O5 to afford 5 in 82% yield and with spectral data in good agreement with those reported in the literature.4
The synthetic route of 2-(Chloromethyl)isoindoline-1,3-dione has been constantly updated, and we look forward to future research findings.
Reference:
Article; Temperini, Andrea; Minuti, Lucio; Tetrahedron Letters; vol. 53; 22; (2012); p. 2709 – 2711;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem