Bromine → 2-bromo-5,6,7,8-tetrahydro-4H-cyclohepta[b]thiophen-4-one

Participants

Reaction Conditions

Reaction Steps

To a solution of 5,6,7,8-tetrahydro-cyclohepta[b]thiophen-4-one (0.5 g, 3 mmol) in 50% aqueous acetic acid (5 mL), cooled to −5° C., was added dropwise a solution of bromine (0.15 mL) in acetic acid (3 mL). The reaction mixture was stirred at −5° C. for 1 hour and quenched into aqueous sodium acetate. The resulting precipitate was filtered off to give the title compound: 1H NMR (300 MHz, CDCl3) δ ppm 7.36 (s, 1 H), 3.01 (m, 2 H), 2.71 (m, 2H), 1.94 (m, 4 H); MS (DCI/NH3) m/z 245 (M+H)+.

Provenance & Evidence