CuCl2 solution (25 × 10⁻⁶ min THF, 1 mL, 25 × 10⁻⁶ mmol) was added to a flame-dried Schrenk tube equipped with a diaphragm and stir bar under a nitrogen atmosphere. n-NonBr (190 μL, 1 mmol) and decane (49 μL, 0.25 mmol) were added as internal standards at room temperature. The reaction mixture was cooled in a dry ice-ethanol bath at -78°C. n-BuMgCl (1.733 min THF, 0.75 mL, 1.3 mmol) was added to the mixture. 1,3-Butadiene (22.4 mL gas, 1 mmol) was injected into the reaction vessel using a syringe, maintaining the temperature at -78°C. The reaction mixture was stirred in a water bath at 25°C for 24 hours. The reaction was quenched by adding 1 N HCl solution. The product was extracted with Et₂O to give the title compound 1-chlorodecane.
