Sodium Bromide → Methyl 3-(2-acetylfuran-3-yl)-6-benzenesulfonylmethyl-2-hydroxybenzoate

Participants

Reaction Conditions

Reaction Steps

A mixture of methyl 6-(benzenesulfonylmethyl)-3-bromo-2-hydroxybenzoate (Intermediate 40, 0.4 g), 2-acetylfuran-3-boronic acid (0.24 g), tetrakis-(triphenylphosphine) palladium (0.12 g), potassium fluoride monohydrate (0.302 g) and sodium bromide (0.192 g) in α,α,α-trifluorotoluene (8 mL) and dioxane (4 mL) was degassed and then heated in the microwave at 175° C. for 30 minutes. The mixture was cooled and ethyl acetate and water were added. The organic layer was separated, washed with water, dried (MgSO4) and filtered. The filtrate was evaporated to dryness and the residue was purified by chromatography on silica, eluting with a mixture of ethyl acetate and cyclohexane with a gradient of 10-25% to give methyl 3-(2-acetylfuran-3-yl)-6-(benzenesulfonylmethyl)-2-hydroxybenzoate (0.21 g) as a white solid.

Provenance & Evidence