反应详情

To a solution of 4-methoxybenzylbromide (2.00 g, 9.95 mmol) in DMF (20 ml) at room temperature was added potassium carbonate (2.07 g, 15.0 mmol) followed by pentafluorothiophenol (1.33 ml, 9.97 mmol). After stirring at room temperature for 1 h, the reaction mixture was poured onto water and extracted with diethyl ether. The combined organic extracts were washed with 1 M NaOH, dried and concentrated to give a white solid which was used directly in the next step. The sulfide (1.11 g, 3.47 mmol) was dissolved in dichloromethane (20 ml) and cooled to 0° C. m-chloroperbenzoic acid, MCPBA, (1.20 g, 6.95 mmol) was added and the resulting mixture stirred at room temperature for 2 h The reaction mixture was poured onto 1 M NaOH (50 ml) and extracted with dichloromethane (3×25 ml). The combined organic extracts were washed with brine, dried (MgSO4),concentrated and flash chromatographed (25:25:1, 20:20:3/hexanes:dichloromethane:ethyl acetate) to provide 413 mg (34%) of the title compound as a white solid. 1H NMR (CDCl3): d 7.18-7.22 (2H, m), 6.85-6.80 (2H, m), 4.48 (2H, s), 3.78 (3H, s). MS (EI): m/z 352 (2, M+), 121 (100). Anal. Calcd for C14H9F5O3S: C, 47.73; H, 2.58; S, 9.10. Found: C, 47.88; H, 2.66; S, 8.97.

1. additionthe reaction mixture was poured onto water
2. extractionextracted with diethyl ether
3. washThe combined organic extracts were washed with 1 M NaOH
4. customdried
5. concentrationconcentrated
6. customto give a white solid which
7. additionwas added
8. stirringthe resulting mixture stirred at room temperature for 2 h The reaction mixture
9. extractionextracted with dichloromethane (3×25 ml)
10. washThe combined organic extracts were washed with brine, dried (MgSO4),concentrated and flash
11. customchromatographed (25:25:1, 20:20:3/hexanes:dichloromethane:ethyl acetate)