反应详情

A mixture of 5-bromo-3H-isobenzofuran-1-one (14 mmol, 3.04 g), benzylzinc bromide solution (0.5 M in THF, 28 mmol, 56 mL), [1,1′bis(diphenylphosphino)-ferrocene]dichloropalladium(II) 1:1 complex with CH2Cl2 (0.07 mmol, 57 mg), and anhydrous 1.4-dioxane (70 mL) was refluxed with stirring under nitrogen for 40 h. After cooling to ambient temperature silica gel was added and the mixture was concentrated in vacuo. The residue was added on top of a chromatography column filled with silica gel. Elution with hexanes:ethyl acetate=9:1 gave a yellow solid. Further purification by recrystallization from ethyl acetate/hexanes gave the title compound (1.37 g) as white needles; 1H NMR (CDCl3, 200 MHz): δ=7.83 (d, 1H), 7.16 to 7.39 (m, 7H), 5.26 (s, 2H), 4.11 (s, 2H).

1. temperaturewas refluxed
2. additionwas added
3. concentrationthe mixture was concentrated in vacuo
4. additionThe residue was added on top of a chromatography column
5. additionfilled with silica gel
6. washElution with hexanes
7. customethyl acetate=9:1 gave a yellow solid
8. customFurther purification
9. customby recrystallization from ethyl acetate/hexanes