General procedure for the synthesis of 2-(5-fluoro-1H-indol-3-yl)ethanol from 5-fluoroindole-3-acetic acid: 5-fluoroindole-3-acetic acid (1 g, 5.2 mmol) was dissolved in anhydrous THF (10 mL) under argon protection, and the ice bath was cooled to 0°C. A 1 M solution of lithium aluminum hydride in THF (10.4 mL, 10.4 mmol) was added slowly dropwise. After the dropwise addition was completed, the ice bath was removed and the reaction mixture was heated to reflux and kept at reflux for 1.5 hours. Upon completion of the reaction, the mixture was cooled to 0°C and the reaction was quenched by the slow addition of water (0.39 mL), 1% NaOH aqueous solution (0.39 mL), and water (0.2 mL) in that order. The insoluble precipitate was removed by vacuum filtration and the filtrate was concentrated under reduced pressure to afford the target product 2-(5-fluoro-1H-indol-3-yl)ethanol as an orange oil (0.927 g, 100% yield). The structure of the product was confirmed by 1H NMR (400 MHz, CDCl3): δ 2.98 (t, J = 6.41 Hz, 2H), 3.89 (t, J = 6.18 Hz, 2H), 6.95 (td, J = 9.04, 2.52 Hz, 1H), 7.12 (s, 1H), 7.22-7.30 (m, 2H), 8.06 (br s, 1H). 1H).
