Iodine → HCID 18385599, compound

Participants

Reaction Steps

A mixed solution of 2-{4-(methylsulfonyl)phenyl}-1,8-dioxa-spiro[4,5]dec-2-en-4-one (0.55 g), [bis(trifluoroacetoxy)iodo]benzene (0.84 g) and iodine (0.45 g) in 50 ml dichloromethane was stirred for 6 hours at room temperature. Then the reaction was quenched by adding 10 ml aqueous saturated sodium thiosulfate. The organic layer was washed with brine and was concentrated under reduced pressure. The resulting crude product was purified by column chromatography (hexane/ethylacetate) to afford 0.6 g of 3-iodo-2-{4-(methylsulfonyl)phenyl}-1,8-dioxa-spiro[4,5]dec-2-en-4-one. mp: 210-213° C. NMR: δ1.60-1.72 (m, 2H), 2.11-2.44 (m, 2H), 3.12 (s, 3H), 3.80-3.90 (m, 2H), 4.04-4.14 (m, 2H), 8.21 (d, J=9 Hz, 2H), 8.41 (d, J=9 Hz, 2H). IR (cm−1): 1690, 1580, 1146, 912, 744.

Provenance & Evidence