Synthesis of linoleoyl bromide (II): A mixture of (9Z,12Z)-octadeca-9,12-dien-1-yl methanesulfonate (6.2 g, 18 mmol) with magnesium bromide in ether (17 g, 55 mmol) in anhydrous ether (300 mL) was stirred under argon protection for 21 hours. After completion of the reaction, the resulting suspension was slowly poured into 300 mL of cold water. After sufficient shaking, the organic phase was separated. The aqueous phase was extracted with ether (2 x 150 mL). All ether phases were combined and washed sequentially with water (2 × 150 mL) and brine (150 mL), then dried with anhydrous Na2SO4. The solvent was evaporated under reduced pressure to give 6.5 g of colorless oily crude product. The crude product was purified by silica gel column chromatography (230-400 mesh, 300 mL) with hexane as eluent to give 6.2 g (about 100% yield) of linoleoyl bromide (II).1H NMR (400 MHz, CDCl3) δ: 5.27-5.45 (4H, m, 2×CH=CH), 3.42 (2H, t, CH2Br), 2.79 (2H, t, C=C-CH2-C=C), 2.06 (4H, q, 2× allyl CH2), 1.87 (2H, quintuple peak, CH2), 1.2-1.5 (16H, m), 0.90 (3H, t, CH3) ppm.
