32337-85-2

1470-94-6

32337-84-1

32337-85-2

5-Indanol (268 g, 2 mmol) was dissolved in 400 mL of N,N-dimethylformamide (DMF) and cooled to 0°C. N-bromosuccinimide (NBS) (2.1 mmol) was added in batches and reacted for 6 h while maintaining the reaction temperature at about 2°C. The reaction was carried out by TLC. The progress of the reaction was monitored by TLC during the reaction. After completion of the reaction, the reaction mixture was poured into 3 L of water and extracted with ethyl acetate (500 mL × 4). The organic phases were combined and washed sequentially with 1N hydrochloric acid solution (500 mL × 2) and saturated brine (500 mL × 2), then dried with anhydrous sodium sulfate. After concentration under reduced pressure, a brown oil was obtained. The light fraction was separated by molecular distillation (conditions: 70 °C, 100 Pa) to afford 4-bromo-2,3-dihydro-1H-inden-5-ol (103.8 g). Further molecular distillation of the recombinant fraction (conditions: 75 °C, 100 Pa) afforded 6-bromo-2,3-dihydro-1H-inden-5-ol (84.5 g). The structure of the product was determined by 1H-NMR (600 MHz, DMSO-d6, δ ppm: 7.49 (d, 1H, J = 7.2 Hz), 7.41 (d, 1H, J = 7.2 Hz), 5.07 (s, 1H), 3.05 (t, 2H), 2.98 (t, 2H), 2.12 (m, 2H)) and ESI-MS (m/z: [M + H]+ 214.0) were confirmed.