To a solution of 2-trifluoromethyl-5-bromopyridine (5.0 g, 22 mmol) in Et2O (50 mL) was added sec-BuLi (0.91 M in cyclohexane, 24 mL, 22 mmol) at -78 °C. After 10 minutes of stirring, N,N-dimethylaminoacetamide (2.3 mL, 24 mmol) dissolved in Et2O (10 mL) was added drop wise. Stirring was continued at -78 °C for 1 h and then at rt over night. The reaction mixture was poured into water (100 mL) and the water phase was extracted with Et2O (3×100 mL). Combined organics were washed with water and brine and dried (MgSO4). After careful evaporation of the solvent, the crude was purified by column chromotography (SiO2, pentane/ether 9/1) to give 1-(6-(Trifluoromethyl)pyridin-3-yl)ethanone (2.3 g, 12 mmol, 54%) as a light yellow solid. 1H NMR (CDCl3) δ 9.26 (br s, 1H) 8.43 (br d, J=5.6 Hz, 1H) 7.83 (br d, J=7.2 Hz, 1H) 2.71 (s, 3H).
