1-bromo-4-propylsulfonylbenzene

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: Add oxone (potassium mono persulfate, 15.03 g, 24.4 mmol) in one portion to a cold (0° C.) stirred solution of 1-bromo-4-propylsulfanyl-benzene (1.881 g, 8.14 mmol) in THF (20 mL), methanol (10 mL), and water (10 mL) and slowly warm to room temperature overnight. Remove the solvents under reduced pressure and add dichloromethane and water to the residue. Separate the layers, extract the aqueous layer twice with dichloromethane, wash the organic layer with saturated aqueous sodium bicarbonate, dry over anhydrous magnesium sulfate, and concentrate under reduced pressure. Purify the residue by flash chromatography (SiO2, elute 0% to 30% EtOAc/hexanes) to yield 1.96 g of the title compound as a colorless oil. 1H NMR (400 MHz, CDCl3) δ 7.80 (d, J=9.2 Hz, 2H), 7.74 (d, J=8.8 Hz, 2H), 3.06-3.11 (m, 2H), 1.72-1.83 (m, 2H), 1.04 (dd, J=7.2, 7.2 Hz, 3H). Remove the solvents under reduced pressure add dichloromethane and water to the residue Separate the layers extract the aqueous layer twice with dichloromethane wash the organic layer with saturated aqueous sodium bicarbonate dry over anhydrous magnesium sulfate concentrate under reduced pressure Purify the residue by flash chromatography (SiO2, elute 0% to 30% EtOAc/hexanes)