4-SF5-toluene (975uL, 1.37 mmol), AIBN (18mg, 0.110 mmol), and NBS (245mg, 1.37 mmol) were charged to a Schlenk flask with 10mL of C2H4Cl2. The resulting mixture was degassed and backfilled twice with N2 and subsequently placed in an oil bath heated to 80C. The mixture was allowed to stir for 24 hours, after which the resulting solution was allowed to cool, and the solvent was removed in vacuo. The resulting residue was charged with diethyl ether, and the solid was filtered away through Celite. The filtrate was dried in vacuo and subjected to silica gel chromatography with a hexane eluent. Fractions containing the desired product, as judged by NMR spectroscopy, were combined, and the solvent was removed to give the desired white solid 4-(Pentafluorosulfur)benzyl bromide (327 mg, 80%).
