Sodium periodate → N-(2-Fluoro-4-formylphenyl)methanesulfonamide

Participants

Reaction Steps

A solution of N-(2-Fluoro-4-vinylphenyl)methansulfonamide (20-2, 1.076 g, 5 mmol) in acetone and water (1:1, 20 mL) was treated with a catalytic amount of osmium tetroxide (4 wt % solution in hydroxyperoxide) and sodium periodate (2.139 g, 10 mmol). After being stirred at room temperature for 1 h, the mixture was concentrated into a small volume in vacuo. The residue was treated with aqueous sodium thiosulfate solution and then extracted with EtOAc several times. The combined organic layers were washed with water and brine, dried over MgSO4, filtered, and the filtrate was concentrated in vacuo. The residue was purified by flash column chromatography on silica gel using EtOAc:hexanes (1:2) as eluant to afford N-(2-Fluoro-4-formylphenyl)methanesulfonamide (20-3, LJO-326, 0.521 g, 48%) as a white solid.

Provenance & Evidence