Sodium Thiosulfate → N-(2-fluoro-3-formyl-phenyl)-4-trifluoromethyl-benzenesulfonamide

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Reaction Steps

To N-(2-fluoro-3-hydroxymethyl-phenyl)-4-trifluoromethyl-benzenesulfonamide (25, 634 mg, 1.82 mmol) in 7 mL of tetrahydrofuran, Dess-Martin periodane (847 mg, 2.00 mmol) and sodium bicarbonate (2 g) were added. The reaction was stirred at room temperature for one hour, then poured into saturated aqueous sodium thiosulfate solution and extracted with ethyl acetate. The organic layer was washed with brine, dried over anhydrous sodium sulfate, filtered and the filtrate concentrated under vacuum. The resulting material was purified by silica gel column chromatography eluting with 15% ethyl acetate in hexane. Appropriate fractions were combined and concentrated under vacuum to provide the desired compound (26, 607 mg, 96%). MS (ESI) [M−H+]−=346.4.

Provenance & Evidence