反应详情

A solution of 6-methoxyisochroman-1-one (15.1 g), N-bromosuccinimide (NBS; 27 g) and benzoyl peroxide (500 mg) in tetrachloromethane (250 ml) was heated to reflux while irradiating with light for 3 hours. The mixture was filtered and the filtrate was concentrated. The residue was dissolved in triethylamine (100 ml) and stirred at room temperature for 48 hours. The reaction mixture was partitioned between water and ethyl acetate and adjusted to pH 1 with concentrated hydrochloric acid. The organic phase was removed, dried over magnesium sulfate and concentrated. The residue was chromatographed on silica gel. The product was thus obtained with the molecular weight of 176.17 (C10H8O3); MS (ESI): 177 (M+H+).

1. temperatureto reflux
2. customwhile irradiating with light for 3 hours
3. filtrationThe mixture was filtered
4. concentrationthe filtrate was concentrated
5. dissolutionThe residue was dissolved in triethylamine (100 ml)
6. customThe reaction mixture was partitioned between water and ethyl acetate
7. customThe organic phase was removed
8. dry with materialdried over magnesium sulfate
9. concentrationconcentrated
10. customThe residue was chromatographed on silica gel
11. customThe product was thus obtained with the molecular weight of 176.17 (C10H8O3)