2-Bromo-5-fluorotoluene

108-88-3

612-75-9

452-63-1

95-46-5

31543-75-6

General procedure: The general procedure for the synthesis of 3,3'-dimethylbiphenyl, 2-bromo-5-fluorotoluene, 2-bromotoluene, and 2,4-dibromotoluene from toluene was as follows: boron trifluoride (TFB) was synthesized directly according to the literature methodology [7-9] before use. The corresponding aromatics (4 mmol) were dissolved in Freon R 113 (4.1 mL) and the solution was cooled to -25 °C. Under vigorous stirring, the corresponding TFB (2 mmol) was slowly added to the aryl hydrocarbon solution, followed by removal of the cooling bath. The reaction mixture was stirred at 45 °C for 5 hours. Upon completion of the reaction, the reaction mixture was treated with H2O and filtered to remove the metal fluoride precipitate. The liquid phase was treated with 10% NaNO2 aqueous solution to remove trace bromine and 30% CaCl2 aqueous solution to remove F- anions. Freon R 113 was removed from the organic phase by evaporation and the resulting product was purified by rapid chromatography on silica gel, the eluent being a hexane:EtOAc solvent mixture.