Step 1: 5-fluoro-2-iodobenzoic acid (5.00 g, 18.80 mmol) was dissolved in tetrahydrofuran (50 mL) and cooled to 0 °C under nitrogen protection. The borane-dimethyl sulfide complex (3.57 mL, 37.60 mmol) was slowly added dropwise under stirring conditions, followed by gradual warming of the reaction mixture to room temperature. The reaction was stirred continuously for 16 hours at room temperature. Upon completion of the reaction, the mixture was carefully poured into ice and quenched by adding 10% aqueous potassium carbonate solution (50 mL). The mixture was extracted with dichloromethane (2 x 50 mL), the organic phases were combined, dried over magnesium sulfate and subsequently concentrated under reduced pressure to give 5-fluoro-2-iodobenzyl alcohol as a colorless solid (4.80 g, 91% yield).1H NMR (400 MHz, CDCl3): δ 7.68 (dd, 1H, J= Hz), 7.19 (dd, 1H, J= Hz), and 6.70 (td, 1H, J= Hz), 4.57 (d, 2H, J= Hz), 1.95 (t, 1H, J= Hz).
