Electric Literature of 5332-26-3,Some common heterocyclic compound, 5332-26-3, name is 2-(Bromomethyl)isoindoline-1,3-dione, molecular formula is C9H6BrNO2, 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.
The starting carborane, 1-C6H5-1,2-C2B10H11 1.00 g (4.53 mmol) dried in vacuum, was dissolved in DME (40 ml) in Schlenk-type flask under argon, and the resulting solution was cooled down to -33 C. and BuLi (2.5 M in hexane, Aldrich, 2.0 ml, 5.0 mmol) was added under stirring from a syringe through septum. The reaction slurry was stirred for 15 min. and then left to warm up to room temperature. The reaction mixture was again cooled down and bromomethyl phtalimide 1.20 g (Aldrich, 5.0 mmol) dissolved in v 15 ml of DME was added dropwise from a syringe. The reaction mixture was stirred for 15 min. -33 C. at and then left slowly to warm up to room temperature over 4 h period. After standing overnight, the solids were filtered off under argon, and washed under argon with two portions of DME (10 ml). Diluted acetic acid (3 M, 0.5 ml) was added to the combined DME extracts and volatiles were removed under reduced pressure. A solid residue was dissolved in benzene and poured atop of a silica gel column (3*25 cm). Elution with benzene led to isolation of the starting 1-Ph-carborane (240 mg), continued elution using benzene-CH3CN (4:1, b.v.) solvent mixture afforded the methylene-phtalimide substituted intermediate carborane 0.85 g (49%).
The synthetic route of 5332-26-3 has been constantly updated, and we look forward to future research findings.