Methyl iodide → 4-Bromo-2-(methanesulfonyl)-1-methoxybenzene

Participants

Reaction Steps

To a suspension of sodium 5-bromo-2-methoxybenzenesulfinate (1.99 g) in DMF (873 ml) was added iodomethane (32 ml). The reaction mixture turned yellow and was stirred at room temperature for 2 hours. The reaction was quenched by the addition of water (ca. 5 ml). The mixture was diluted with EtOAc and extracted with 5% LiCl (3×) and brine (1×). The organic layer was dried (Na2SO4/MgSO4) and filtered. The filtrate was concentrated and purified by silica gel column chromatography to give 1.62 g 4-bromo-1-methoxy-2-(methylsulfonyl)benzene as a white crystalline solid.

Provenance & Evidence