Cesium carbonate → 2-(4-Fluorophenyl)-6-(phenylsulfonyl)naphthalene

Participants

Reaction Conditions

Reaction Steps

A mixture of 6-(4-fluorophenyl)-2-naphthyl trifluoromethanesulfonate (Step 2, 260 mg, 0.7 mmol), cesium carbonate (345 mg, 1.06 mmol), sodium benzenesulfinate (140 mg, 0.85 mmol), tris(dibenzylideneacetone)dipalladium(0) (16 mg), 4,5-bis(diphenylphosphino)-9,9-dimethylxanthene (20 mg) and tert-butylammonium chloride (235 mg, 0.84 mmol) in toluene (5 mL) was heated to 120° C. under nitrogen for 5 hours. The cooled reaction mixture was poured into water and extracted with ethyl acetate (x3). The combined organic layers were washed with water and brine, dried over MgSO4 and evaporated in vacuo. The residue was purified by flash column chromatography on silica, eluting with 20% ethyl acetate/isohexane, followed by trituration with 10% diethyl ether/isohexane to give the title compound as an off-white solid (180 mg, 71%). 1H NMR (500 MHz, CDCl3) δ 8.59 (1H, s), 8.05-7.95 (5H, m), 7.88 (1H, dd, J=1.8, 8.6 Hz), 7.81 (1H, dd, J=1.7, 8.5 Hz), 7.67-7.65 (2H, m), 7.57-7.49 (3H, m), 7.20-7.16 (2H, m).

Provenance & Evidence