Acetic Acid → HCID 18385639, compound

Participants

Reaction Steps

To 147 mg of 2-{4-(methylthio)phenyl}-1-oxa-spiro[4,4]non-2-en-4-one in 30 ml carbon tetrachloride, were added 1 ml bromine and 0.1 ml acetic acid. The reaction mixture was stirred for 1 hour at room temperature. Then the reaction was quenched by adding saturated aqueous sodium thiosulfate solution until the characteristic color of bromine disappeared. The quenched solution was extracted with dichloromethane (10 ml×3). The organic layer was concentrated under reduced pressure and the resulting residue was purified by column chromatography (hexane/ethylacetate) to yield 50 mg of 3-bromo-2-{4-(methylthio)phenyl}-1-oxa-spiro[4,4]non-2-en-4-one. NMR: δ1.98 (m, 4H), 2.11 (m, 4H), 2.55 (s, 3H), 7.32 (d, J=8.7 Hz, 2H), 8.13 (d, J=8.7 Hz, 2H).

Provenance & Evidence