4-Phenoxyphenol → 2-chloro-4-phenoxyPhenol

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To a 54 ml toluene solution of 4-phenoxyphenol (2 g, 10.7 mmol) and diisobutylamine (0.15 ml, 0.86 mmol) was added sulfuryl chloride (0.69 ml, 8.6 mmol). The mixture was heated to 70° C. for 3 hr. The solvent was removed under reduced pressure. The residue was diluted with AcOEt and aq sat. bicarbonate solution. The organic layer was separated, and the aqueous layer was extracted twice with AcOEt. The combined organic layers were dried over anhydrous Na2SO4, filtered, concentrated, and chromatographed on silica gel. Elution with 15% AcOEt/hexanes gave the title compound 2.3 g as colorless syrup (97%).

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