Sodium hydride → 4-(4-Bromo-benzyl)-thiomorpholine 1,1-dioxide

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Reaction Steps

A mixture of thiomorpholine 1,1-dioxide (270 mg, 2.0 mmol) in DMF (10 ml) was prepared at room temperature and sodium hydride (60 wt % in oil, 96 mg, 2.40 mmol) added in one portion and the mixture stirred at room temperature for 1 h. 1-Bromo-4-(bromomethyl)benzene was then added in one portion and the mixture stirred overnight for 17.5 h under argon. The mixture was then quenched with saturated aqueous ammonium chloride solution (10 ml) and diluted with ethyl acetate (30 ml). The mixture was partitioned and the aqueous layer removed. The organic layers were then washed with 5% aqueous lithium chloride solution (2×10 ml), brine (10 ml), dried over magnesium sulphate and the solvent removed under reduced pressure. The crude product was then purified by column (0-5% methanol/dichloromethane) to afford 4-(4-bromobenzyl)thiomorpholine 1,1-dioxide as a colourless solid (283 mg, 0.93 mmol, 47%).

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