Step 1: Bromine (16.5 g, 0.103 mol) was added dropwise to a solution of triphenylphosphine (27.8 g, 0.103 mol) in dichloromethane (200 mL) at 0°C while stirring. After the dropwise addition was completed, stirring of the reaction mixture was continued for 10 minutes. Subsequently, 4-chloro-3-fluorobenzyl alcohol (15.8 g, 0.098 mol) was added and the reaction mixture was stirred for 30 minutes. Upon completion of the reaction, the reaction was quenched with ethanol and the mixture was poured into saturated sodium bicarbonate solution and extracted with dichloromethane. The organic phases were combined, dried with anhydrous sodium sulfate, filtered and concentrated. Purification by silica gel column chromatography afforded 4-(bromomethyl)-1-chloro-2-fluorobenzene (18.6 g, 85% yield).1H-NMR (400 MHz, CDCl3): δ = 7.27 (t, J = 7.9 Hz, 1H), 7.10 (dd, J = 7.9 Hz, 2.1 Hz, 1H), 7.04-6.99 (m, 1H). 4.32 (s, 2H).
