Benzyl phenyl sulfide → Benzyl phenyl sulfoxide

Participants

Reaction Steps

To a solution of benzyl phenyl sulfide (Aldrich; 1.068 g, 5.33 mmol) in 25 mL of CH2Cl2 at -78° C. was slowly added a solution of m-chloroperbenzoic acid (Aldrich, 50-60%; 760 mg, 2.64 mmol if 60%) in 10 mL of CH2Cl2. After warming to room temperature and stirring overnight, the solution was added to 20 mL of a saturated NaHCO3 solution. The aqueous layer was separated and extracted with CH2Cl2 (2×10 mL). The pooled organic layers were then dried (MgSO4) and concentrated. The residue was subjected to flash column chromatography (silica gel, 10% acetone/hexane and 15% acetone/hexane) affording the sulfoxide (632 mg, 55%) as a white solid, mp 123°-126° C. 1H NMR (CDCl3, 300 MHz) δ7.40-7.15 (m, 8H), 6.91 (d, 2H, J=7.8 Hz), 4.03 (d, 1H, J=12.6 Hz), 3.93 (d, 1H, J=12.6 Hz).

Provenance & Evidence