In a dry reaction flask, the dimethylborane sulfide complex (2.7 mL, 28 mmol) was slowly added dropwise to a solution of 11-bromo-1-undecanoic acid (20 mmol) in tetrahydrofuran (30 mL). The reaction solution was stirred at room temperature for several hours, and the resulting reaction mixture was stirred at 45°C for approximately 1 hour. The reaction progress was monitored by TLC. After the reaction was complete, the resulting reaction mixture was cooled at 0°C, quenched with methanol (60 mL), and then concentrated under vacuum. The resulting residue was then dissolved in ethyl acetate, washed with brine, dried with Na₂SO₄, filtered to remove the drying agent, and the resulting organic solvent was concentrated under vacuum to obtain the target product molecule, 11-Bromo-1-undecanol.
