p-Tolyl methyl sulfone → 2-Bromo-4-(methanesulfonyl)-1-methylbenzene

Participants

Reaction Steps

To a solution of elemental iron (67 mg, 1.2 mmol) in Br2 (2.05 mL, 39.9 mmol) was added 4-methanesulfonyl-1-methyl-benzene (340 mg, 2.0 mmol) at 0° C. The reaction mixture was stirred at room temperature for 2 hrs. TLC (petroleum ether:EtOAc 3:1) indicated the reaction was completed. Then the mixture was poured into an ice-cold aqueous Na2S2SO3 (1M, 10 mL) and extracted with EtOAc (20 mL×3), washed with brine (10 mL×3), dried over sodium sulfate, concentrated in vacuum, and the residue was purified by a Biotage silica gel cartridge (petroleum ether/EtOAc 3:1, Rf˜0.6) to give the title compound (300 mg, 80%) as a white solid.

Provenance & Evidence