反应详情

To a stirred solution of N-hydroxyphthalimide (0.60 g, 3.68 mmol) and Et3N (0.60 mL, 4.30 mmol) in DMF (6 mL) was added α,α′-dibromo-o-xylene (3.30 g, 0.0125 mol) and the mixture stirred at room temperature for 4 h. The resultant brown precipitate was filtered and washed with CH2Cl2. The filtrate was diluted with EtOAc (40 mL) and water (30 mL) and the organic phase washed with brine (1×30 mL), dried (Na2SO4) and concentrated under reduced pressure. The resultant yellow oil was purified by column chromatography on silica gel (4:1 Hexanes/EtOAc) to give the title compound (581 mg, 46%) as a white solid. 1H NMR (CDCl3) δ 4.99 (s, 2H), 5.37 (s, 2H), 7.27–7.40 (m, 2H), 7.41–7.45 (m, 2H), 7.73–7.76 (m, 2H), 7.81–7.84 (m, 2H).

1. filtrationThe resultant brown precipitate was filtered
2. washwashed with CH2Cl2
3. additionThe filtrate was diluted with EtOAc (40 mL) and water (30 mL)
4. washthe organic phase washed with brine (1×30 mL)
5. dry with materialdried (Na2SO4)
6. concentrationconcentrated under reduced pressure
7. customThe resultant yellow oil was purified by column chromatography on silica gel (4:1 Hexanes/EtOAc)