2927-34-6

108-88-3

352-32-9

95-52-3

352-70-5

452-76-6

452-67-5

2927-34-6

The general procedure for the synthesis of p-fluorotoluene, 2-fluorotoluene, 3-fluorotoluene, 2,4-difluorotoluene, 2,5-difluorotoluene, and 1,2-difluoro-4-methylbenzene from toluene is as follows: to a glass reactor equipped with a PTFE-lined magnetic stirring bar connected to a gas scrubber bottle, toluene (0.95-1.14 mmol), acetonitrile (1-2.5 mL/mmol toluene), and a boron trifluoride ethyl ether complex (1.3-1.6 mmol/mmol toluene) were added. mmol toluene), acetonitrile (1-2.5 mL/mmol toluene) and boron trifluoride ethyl ether complex (1.3-1.6 mmol/mmol toluene). The reaction solution was stirred at -25°C for 10-15 minutes, followed by the addition of xenon difluoride (1.2-1.3 mmol/mmol toluene) in batches. The reaction mixture was slowly warmed to 22 °C over 1 h and stirring was continued for 40-60 min. Upon completion of the reaction, hexafluorobenzene was added as an internal standard and the sample was removed for 19F NMR analysis (Method B). The reaction mixture was quenched with saturated aqueous sodium bicarbonate and extracted with dichloromethane (1-2 mL). The organic extract was dried over anhydrous magnesium sulfate and analyzed by 19F NMR and GC/MS (Procedure C). The major products are listed in the table and the remaining products are shown below (GC/MS data).