Acetone → 1-Acetyl-6-bromospiro[indoline-3,3'-thietane]1',1'-dioxide

Participants

Reaction Steps

To a stirred ice-cooled solution of 1-acetyl-6-bromo-1,2-dihydrospiro[indole-3,3′-thietane] (0.288 g, 0.97 mmol) in a mixture water (2.4 mL), MeOH (18.9 mL), and acetone (4.7 mL) was added a solution of oxone (1.19 g, 1.93 mmol) in water (1.8 mL). The ice bath was removed and the solution was stirred at rt for 4 h. The mixture was poured into saturated aqueous ammonium chloride and extracted with EtOAc. The combined organic extracts were dried over MgSO4, filtered and evaporated in vacuo to give 1-acetyl-6-bromo-1,2-dihydrospiro[indole-3,3′thietane]1′,1′-dioxide as a tan solid. Mass Spectrum (ESI) m/e=330.0 [(M+1) (79Br)] and 332.0 [(M+1) (81Br)].

Provenance & Evidence