p-Bromobenzenesulfonyl chloride → 1-(4-Bromophenylsulfonyl)-1H-pyrrole

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Reaction Steps

Pyrrole (1.05 mL, 15.0 mmol) was added to a slurry of sodium hydride (0.71 g, 60% in mineral oil, 17.8 mmol) in dry THF (10 mL) at room temperature. 4-Bromobenzene sulfonyl chloride (1.5 g, 6.0 mmol) dissolved in dry THF (5 mL) was added dropwise. The reaction mixture was stirred overnight. The reaction was quenched with saturated ammonium chloride and diluted with ethyl acetate. The layers were separated and the organic layer was washed with water and brine. The organic layer was dried over anhydrous sodium sulfate, filtered and concentrated in vacuo to give the crude product. The crude product was purified via Isco chromatography (the Redisep™ column, silica, gradient 5-50% ethyl acetate in hexane) to give 1-[(4-bromophenyl)sulfonyl]-1H-pyrrole (0.27 g, 16%). MS (ESI) m/z 286. HPLC purity 100.0% at 210-370 nm, 9.9 min.; the Xterra® RP18 column, 3.5μ, 150×4.6 mm column 1.2 mL/min., 85/15-5/95 (ammonium formate buffer pH=3.5/ACN+MeOH) for 10 min., hold 4 min.

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