Cesium fluoride → 4-(methylsulfonyl)-2-nitro-1-[(1E)-prop-1-en-1-yl]benzene

Participants

Reaction Conditions

Reaction Steps

A mixture of 2-bromo-5-methylsulfonylnitrobenzene (1.50 g; 5.36 mmol), trans-propenylboronic acid (690 mg; 8.03 mmol), caesium fluoride (2.44 g; 16.1 mmol) and bis(triphenylphosphine)palladium(II) chloride (376 mg; 0.54 mmol) was degassed with nitrogen, then treated with dioxane (30 ml) and water (15 ml). The resulting reaction mixture was heated at 80° C. for 2 hours, taken up in EtOAc and washed with water and brine. The organic phase was dried on MgSO4, filtered and concentrated under reduced pressure to give a residue which was purified by by flash column chromatography, eluting with cyclohexane containing increasing amounts of EtOAc. The title compound was obtained as an off-white solid (1.10 g, 85%).

Provenance & Evidence