Sodium Bicarbonate → 5-Bromo-1,3-dihydro-benzo(c)thiophene 2,2-dioxide

Participants

Reaction Conditions

Reaction Steps

Dissolve 5-bromo-1,3-dihydro-benzo[c]thiophene (1.25 g, 5.79 mmol) in methanol (25 mL) and add oxone (10.7 g, 17.4 mmol). Stir the reaction mixture for 2 hours at 0° C. and then add a 1M aqueous sodium bisulfite solution (100 mL). Stir the reaction mixture for 10 minutes and add saturated NaHCO3 solution (200 mL). Extract the aqueous layer with CH2Cl2 (3×100 mL). Combine the organic layers and dry with Na2SO4, filter, concentrate and purify by flash column chromatography (silica gel, 0-5% MeOH/CH2Cl2) to give 930 mg of 5-bromo-1,3-dihydro-benzo[c]thiophene 2,2-dioxide 65%).

Provenance & Evidence