Sodium methanesulfinate → 6-Methanesulfonyl-2-methyl-3-nitropyridine

Participants

Reaction Steps

A mixture of 6-bromo-2-methyl-3-nitropyridine (100 g, 461 mmol) and sodium methanesulfinate (47.0 g, 461 mmol) in DMSO (300 mL) was stirred at room temperature for 1.5 h. The reaction mixture was poured into ice-water (1 L) and stirred until all the ice had melted. The ice-cold solution was filtered, and a dark purple solid was collected. The solid collected was dissolved in ethyl acetate (1 L). The solution was treated with activated charcoal, filtered through Celite™. The Celite™ cake was washed with ethyl acetate, and the filtrate was collected. The solvent was evaporated from the filtrate under reduced pressure to give the title compound (87.0 g, 87%) as a yellow solid. Exact mass calculated for C7H8N2O4S: 216.0. Found: LCMS m/z=217.2 (M+H+).

Provenance & Evidence