Water → 4-[3,5-Difluoro-4-(methylsulfinyl)phenyl]-5-methyl-3-phenylisoxazole

Participants

Reaction Steps

To a solution of 4-[3,5-difluoro-4-(methylthio)phenyl]-5-methyl-3-phenylisoxazole in dichloromethane (75 mL) and methanol (15 mL) cooled in an ice bath was added magnesium monoperoxyphthalate hexahydrate (4.4 g 80%, 7.1 mmol) in portions over 5 minutes. The reaction mixture was stirred for 90 minutes, then poured into water and extracted with dichloromethane (1×250 mL, 1×75 mL). The combined extracts were washed with dilute ammonium chloride, dried with magnesium sulfate, and concentrated. Purification by silica gel chromatography using 25% ethyl acetate/25% hexanes/50% dichloromethane gave 4-[3,5-difluoro-4-(methylsulfinyl)phenyl]-5-methyl-3-phenylisoxazole as a white solid. 1H NMR (CDCl3/400 MHz) 7.37-7.44 (m, 5H), 6.77-6.81 (m, 2H), 3.13 (s, 3H) 2.50 (s, 3H). HRMS m/z 334.0698 (M+H+, calcd 334.0713). Anal. Calcd for C17H13F2NO2S: C, 61.25; H, 3.93; N, 4.20; Found: C, 61.22; H, 4.00, N 4.02.

Provenance & Evidence