反应详情

To a suspension of N-iodosuccinimide (1.12 g, 0.005 mol) in acetic acid (15.0 mL) was added 4-(difluoromethoxy)phenol (0.8 g, 0.005 mol) under nitrogen. Sulfuric acid (0.147 g, 0.0015 mol) was added and the resulting dark brown suspension was stirred at room temperature for 4 hours before the addition of N-iodosuccinimide (0.6 g, 0.0025 mol). The mixture was stirred for 16 hours before diluting with citric acid (1.0 M aqueous solution, 20.0 mL) and water (20.0 mL). The aqueous layer was extracted with dichloromethane (2×30.0 mL). Combined organic layers were dried over sodium sulphate, filtered and concentrated in vacuo to afford a dark purple oil. This was concentrated in vacuo from toluene (3×20.0 mL) to afford a brown oil. The aqueous layer was concentrated in vacuo. Both organic and aqueous crude residues were purified by flash column chromatography on the ISCO™ (40 g SiO2) eluting with ethyl acetate:heptane (gradient 0:1 to 1:1, by volume) to afford the title compound as a yellow oil, 0.604 g, 42% yield.

1. extractionThe aqueous layer was extracted with dichloromethane (2×30.0 mL)
2. dry with materialCombined organic layers were dried over sodium sulphate
3. filtrationfiltered
4. concentrationconcentrated in vacuo
5. customto afford a dark purple oil
6. concentrationThis was concentrated in vacuo from toluene (3×20.0 mL)
7. customto afford a brown oil
8. concentrationThe aqueous layer was concentrated in vacuo
9. customBoth organic and aqueous crude residues were purified by flash column chromatography on the ISCO™ (40 g SiO2)
10. washeluting with ethyl acetate