808127-76-6

808127-75-5

808127-76-6

Example 104B Synthesis of 4-bromo-6-hydroxy-1-isodihydroindolone: Example 104A (4-bromo-2,3-dihydro-6-methoxy-1H-isoindol-1-one, 100 mg, 0.41 mmol) was dissolved in dichloromethane (13 mL) to form a -78 °C suspension. At this temperature, a dichloromethane solution of 1 M BBr3 (1.2 mL, 1.2 mmol) was added dropwise and stirred at -78 °C for 1 h. The mixture was then brought to room temperature and continued to be stirred for 2 h. The reaction mixture was then stirred for 1 h at -78 °C. The reaction mixture was again treated with a dichloromethane solution (0.8 mL) of 1 M BBr3 and heated to reflux overnight. After completion of the reaction, it was cooled to room temperature and extracted by partitioning with water and ethyl acetate. The organic phase was dried over anhydrous sodium sulfate (Na2SO4), filtered and concentrated to afford the target product 4-bromo-2,3-dihydro-6-hydroxy-1H-isoindol-1-one (91 mg, 97% yield). Mass spectrum (ESI negative ion mode) m/z: 226, 228 ([M-H]-).