α-Chlorothioanisole

Typical Procedure:
[Protection of p-bromophenol]
To a solution of p-bromophenol (0.692 g, 4.00 mmol) in dry HMPA (distilled from CaH₂) (20 mL) under N₂ is added sodium hydride (0.106 g, 4.40 mmol). After stirring at room temperature for 0.5 h, chloromethyl phenyl sulfide (0.636 g, 4.00 mmol) and sodium iodide (0.600 g, 4.00 mmol) are added and stirring at room temperature is continued for 18 h. The mixture is partitioned between benzene and water; drying and evaporation of benzene extracts gives an oil which is purified by Kugelrohr distillation to provide pure product (1.03 g, Y. 87%).
[Deprotection]
To a solution of p-bromophenyl phenylthiomethyl ether (0.295 g, 1.00 mmol) in CH₃CN―H₂O (4:1, 10 mL) is added mercuric chloride (0.407 g, 1.50 mmol). The resulting suspension is refluxed for 42 h, diluted with ethyl ether, and filtered through celite. Aqueous extraction followed by drying and solvent evaporation gives spectrally and chromatographically pure p-bromophenol (0.155 g, Y. 90%).