To a stirred solution of p-chloroiodobenzene (15.0 g, 63 mmol) and ethyl difluorobromoacetate (12.8 g, 63 mmol) in DMSO (300 mL) was added copper powder (8.0 g). The mixture was heated to 80 °C and stirred for 20 hours. After the reaction was completed, the mixture was cooled to room temperature and poured into an aqueous solution (1.5 L) of K2HPO4-3H2O (11.0 g). After stirring for 30 min at room temperature, the mixture was filtered through a diatomaceous earth pad and the filter cake was washed with ether. The combined organic phases were washed sequentially with water and brine, dried with Na2SO4 and concentrated. Purification by silica gel column chromatography (eluent: hexane) afforded ethyl 2-(4-chlorophenyl)-2,2-difluoroacetate as a colorless oil (6.8 g, 46% yield).1H NMR (400 MHz, CDCl3) δ 7.55 (d, J = 8.4 Hz, 2H), 7.44 (d, J = 8.4 Hz, 2H), 4.30 (q, J = 7.1 Hz, 2H), 1.31 (t, J = 7.1 Hz, 3H).
