Hydrochloric Acid → 2-(Phenylsulfonyl)benzenesulfonyl chloride

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Reaction Steps

To a solution of 2-(phenylsulfonyl)aniline (2.33 g, (10 mmol) in 30% aqueous hydrochloric acid (4 mL) was added 40% aqueous sodium nitrite (4 mL) at 0-5° C. After 15 minute, to the diazo solution were added 30% aqueous hydrochloric acid (10 mL), cooper sulfate (50 mg) and 40% aqueous sodium bisulfite (10 mL) at 5-10° C. The mixture was stirred for 30 minutes and additional water (30 mL) was added. The mixture was extracted into dichloromethane (3×40 mL) and the dichloromethane solution was washed with brine (40 mL) and dried over Na2SO4. After removing the solvent in vacuo, the residue was purified by flash column chromatography (dichloromethane) to give the title compound as a white solid (2.1 g, 66%). 1H-NMR (300 MHz, CDCl3) δ8.62 (d, J=7.8 Hz, 1H), 8.34 (d, J=7.9 Hz, 1H), 7.85-7.98 (m, 4H), 7.48-7.63 (m, 3H).

Provenance & Evidence