General procedure for the synthesis of bromotetradecane from 1-tetradecene: 1-tetradecene (393 mg, 2 mmol) was dissolved in hexane (2 mL) at room temperature, followed by the addition of 1c (17 wt%, 1.3 g, 2.7 mmol). The reaction mixture was stirred for 1 h at room temperature. Upon completion of the reaction, the reaction was quenched with deionized water (10 mL) and extracted with ether (10 mL × 3). The organic phases were combined, washed with saturated saline (15 mL × 2), dried over anhydrous sodium sulfate (5 g), and concentrated under reduced pressure to remove the solvent. The crude product was purified by silica gel column chromatography using hexane as eluent to afford bromotetradecane (543 mg, 98% yield) as a colorless liquid. The structure of the product was confirmed by 1H-NMR (500 MHz, CDCl3) and 13C NMR (126 MHz, CDCl3): 1H-NMR δ 0.89 (t, J = 6.9 Hz, 3H), 1.26-1.31 (m, 18H), 1.84 (dd, J = 7.7 Hz, J = 6.7 Hz, 2H), 3.41 (t, J = 6.9 Hz, 2H); 13C NMR δ 14.21, 22.85, 28.38, 28.97, 29.55, 29.64, 29.74, 29.85 (4C), 32.11, 33.03, 33.59.
