m-Chloroperbenzoic acid → HCID 59540594, compound

Participants

Reaction Steps

To a mixture of 4-(3-bromo-5-methoxy-phenyl)-thiomorpholine (239 mg, 0.83 mmol) in methylene chloride (10 ml) and methanol (5 drops) was added m-CPBA (409 mg, 1.83 mmol). After 1 hour methanol (10 drops) was added to enhance solubility. The mixture was stirred another 3 hours. Methylene chloride (25 ml) and a 10% solution of aqueous sodium metabisulfite (35 ml) were added and the material was shaken in a reparatory funnel. The organic phase was collected and washed consecutively with equal volumes of 5% aqueous sodium bicarbonate and then brine solution. The aqueous phases were back-extracted with methylene chloride (2×25 ml), the organic phases combined, dried (MgSO4), filtered and stripped to a crude residue. The material was loaded onto 2 preparative TLC plates, eluting with 40% ethyl acetate in hexanes. The product band was collected to afford 76 mg of 4-(3-bromo-5-methoxy-phenyl)-thiomorpholine 1,1-dioxide as a off-white solid.

Provenance & Evidence