New downstream synthetic route of 5332-26-3

The chemical industry reduces the impact on the environment during synthesis 2-(Bromomethyl)isoindoline-1,3-dione. I believe this compound will play a more active role in future production and life.

Reference of 5332-26-3, 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. 5332-26-3, name is 2-(Bromomethyl)isoindoline-1,3-dione, This compound has unique chemical properties. The synthetic route is as follows.

A suspension of N-(bromomethyl)phthalimide (3.6g, 15.0mmol) in triethylphosphite (3.00g, 18.0mmol) was heated to 90Cfor 3h. A distillation apparatus was then installed and volatile ethyl bromide was removed by reduced pressure distillation. The crude mixture was cooled to room temperature, and the resulting white solid was used without further purification. 1H NMR (300MHz, CDCl3) delta=1.24 (t, J=7.1Hz, 6H, 2¡ÁCH3), 4.01 (d, 2JH-P=11.4Hz, 2H, 1¡ÁCH2), 4.12 (m, 4H, 2¡ÁCH2), 7.73 (dd, J=5.5, 3.1Hz, 2H, 2¡ÁCH), 7.86 (dd, J=5.3, 3.0Hz, 2H, 2¡ÁCH) ppm. To a solution of this solid (4.5g, 15mmol) in ethanol (20mL) was added hydrazine monohydrate (1.05mL, 21.6mmol) and the resulting mixture was stirred at room temperature overnight, and then refluxed for 3h. The crude mixture was cooled down to 0C, and the white precipitate was removed by filtration and washed with ice-cold ethanol. The solution was concentrated under vacuum, and the resulting oily residue was purified by column chromatography on silica gel eluting with a gradient of Et2O/ MeOH (80:20?70:30) to afford compound 24 as a pale yellow oil (2.43g, 97%). TLC: Rf=0.30 (silica gel, Et2O/MeOH 80:20, stained with ninhydrin). 1H NMR (300MHz, CD3CN) delta=1.31 (t, J=7.1Hz, 6H, 2¡ÁCH3), 1.76 (br, 2H, NH2), 2.94 (d, 2JH-P=10.6Hz, 2H, 1¡ÁCH2), 4.08 (quintet, 3JH-H=3JH-P=7.0Hz, 2H, 1¡ÁCH2), 4.10 (quintet, 3JH-H=3JH-P=7.1Hz, 2H, 1¡ÁCH2) ppm. 31P NMR (121MHz, CDCl3) delta=27.49ppm.

The chemical industry reduces the impact on the environment during synthesis 2-(Bromomethyl)isoindoline-1,3-dione. I believe this compound will play a more active role in future production and life.

Reference:
Article; Leygue, Nadine; Perez e Iniguez De Heredia, Aritz; Galaup, Chantal; Benoist, Eric; Lamarque, Laurent; Picard, Claude; Tetrahedron; vol. 74; 31; (2018); p. 4272 – 4287;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem