Sodium Bromide → Ethyl 6-benzenesulphonylmethyl-3-(furan-3-yl)-2-hydroxybenzoate

Participants

Reaction Conditions

Reaction Steps

A mixture of ethyl 6-(benzenesulphonylmethyl)-3-bromo-2-hydroxybenzoate (Intermediate 52, 0.39 g), furan-3-yl boronic acid (0.16 g), potassium fluoride monohydrate (0.45 g), tetrakis-(triphenylphosphine) palladium (0.11 g), and sodium bromide (0.15 g) in α,α,α-trifluorotoluene (10 ml) and dioxane (2 ml) was degassed and heated in the microwave at 175° C. for 30 minutes. After cooling, the mixture was partitioned between ethyl acetate and water. The aqueous layer was further extracted with ethyl acetate and the combined organic layers were dried (Na2SO4) 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 15-30% to give ethyl 6-benzenesulphonylmethyl-3-(furan-3-yl)-2-hydroxybenzoate (0.25 g) as a white solid.

Provenance & Evidence