General procedure for the synthesis of 2-fluoro-5-nitrotoluene from 2-chloro-5-nitrotoluene: To an oven-dried resealable reaction tube fitted with a stirrer were added aryl halide (20, 0.12 mmol), BrettPhos (6.4 mg, 0.012 mmol, 10 mol%), (COD)Pd(CH2TMS)2 (2.3 mg. 0.006 mmol, 5 mol%), AgF (23 mg, 0.18 mmol) and toluene (2 mL). The reaction tube was then sealed with a screw cap and removed from the glove box, wrapped in aluminum foil and placed in an oil bath preheated to the indicated temperature with thorough stirring. After 12 hours of reaction, the reaction tube was removed from the oil bath and cooled to room temperature. 4-Fluorotoluene (13.2 μL, 0.12 mmol, 1 eq.) and dodecane (27.3 μL, 0.12 mmol, 1 eq.) were added as internal standards. The reaction mixture was filtered through a glass filter fitted with Celite to remove all solids. Finally, the product yield was analyzed by 19F NMR (282 MHz) and the conversion was determined by GC.
