反应详情

温度

30 °C

A tricol of 1 L with a condenser and an addition funnel is purged with N2 and magnesium turnings (5 g, 206 mmol) in tetrahydrofuran (80 mL) are added. Bromobenzene (32 g, 206 mmol) in tetrahydrofuran (80 mL) is added dropwise over 1¼ hour by maintaining the mixture temperature at 30° C. The resulting mixture is stirred for 45 min. at 30° C. 4-Bromo-2-formyl-benzoic acid (C3) (18.9 g, 83 mmol) in anhydrous tetrahydrofuran (200 mL) is added dropwise over 45 min. The mixture is stirred for 2 h at 30° C. The mixture is cooled in an ice-water bath and water (120 mL) and 5N HCl solution (80 mL) are added. The mixture is stirred overnight. THF is removed in vacuo and extracted with DCM (3×100 mL). The combined organics are washed with water (2×100 mL), dried over Na2SO4, filtered and the solvent is removed in vacuo to yield 5-bromo-3-phenyl-3H-isobenzofuran-1-one (22.5 g, 94%). Recrystallization: 5-bromo-3-phenyl-3H-isobenzofuran-1-one is dissolved in hot acetone (250 mL) and the mixture cooled in an ice-water bath over night. The resultant solid is filtered, rinsed with cold ACN (2×15 mL), and then vacuum dried over KOH to yield 5-bromo-3-phenyl-3H-isobenzofuran-1-one (D3) (14.4 g, 61%, mp: 189° C.).

1. additionare added
2. stirringThe mixture is stirred for 2 h at 30° C
3. temperatureThe mixture is cooled in an ice-water bath
4. stirringThe mixture is stirred overnight
5. customTHF is removed in vacuo
6. extractionextracted with DCM (3×100 mL)
7. washThe combined organics are washed with water (2×100 mL)
8. dry with materialdried over Na2SO4
9. filtrationfiltered
10. customthe solvent is removed in vacuo