Acetyl chloride → 1-Acetyl-6-bromo-1,2-dihydrospiro[indole-3,3'-thietane]

Participants

Reaction Steps

To an ice cooled solution of 6-bromo-1,2-dihydrospiro[indole-3,3′-thietane] (0.25 g, 0.96 mmol), 4-dimethylaminopyridine (5.89 mg, 0.048 mmol), and triethylamine (0.269 mL, 1.928 mmol) in DCM (9.64 mL) was added acetyl chloride (0.137 mL, 1.928 mmol). The solution was stirred for 5 min at this temperature, the ice bath was removed and the solution was stirred at rt for 3 h. The reaction was poured into 2N HCl aqueous solution and extracted with EtOAc. The combined organic extracts were dried over MgSO4 and concentrated under reduced pressure to give 1-acetyl-6-bromo-1,2-dihydrospiro[indole-3,3′-thietane] as a yellow solid. Mass Spectrum (ESI) m/e=297.9 [(M+1) (79Br)] and 300.0 [(M+1) (81Br)].

Provenance & Evidence