Ammonium Chloride → 6-Bromospiro[indoline-3,3'-thietan]-2-one

Participants

Reaction Conditions

Reaction Steps

To a solution of tert-butyl 6-bromo-3,3-bis((methylsulfonyloxy)methyl)-2-oxoindoline-1-carboxylate (3.70 g, 7.0 mmol) in anhydrous DMF (33 mL, deoxygenated with argon for 10 min) was added sodium sulfide nonahydrate (1.01 g, 4.20 mmol) under an argon atmosphere. The solution was stirred at 110° C. for 3 h, poured into saturated aqueous ammonium chloride solution and extracted with EtOAc. The combined organic extracts were dried over MgSO4, filtered and evaporated in vacuo. Purification by column chromatography (eluting with a gradient of 10-50% EtOAc in hexanes) gave 6-bromospiro[indoline-3,3′-thietan]-2-one as a yellow solid. Mass Spectrum (ESI) m/e=270.0 [(M+1) (79Br)] and 271.9 [(M+1) (81Br)].

Provenance & Evidence