Trifluoromethanesulfonic anhydride → 6-(4-Fluorophenyl)-2-naphthyl trifluoromethanesulfonate

Participants

Reaction Conditions

Reaction Steps

Trifluoromethanesulfonic anhydride (1.3 mL, 7.74 mmol) was added over 5 minutes to a stirred solution of 6-(4-fluorophenyl)-2-naphthol (Step 1, 1.75 g, 7.35 mmol) in dichloromethane (25 mL) and pyridine (15 mL) at 0° C. under nitrogen. The reaction was stirred at 0° C. for 1 hour then allowed to warm to room temperature. The solvent was removed in vacuo and the residue partitioned between ethyl acetate and water. The combined organic layers were washed with water and brine, dried over MgSO4 and evaporated in vacuo to give 6-(4-fluorophenyl)-2-naphthyl trifluoromethanesulfonate (2.34 g, 86%). 1H NMR (500 MHz, CDCl3) δ 8.03 (1H, s), 7.96 (2H, dd, J=9.1, 13.1 Hz), 7.81-7.77 (2H, m), 7.67-7.65 (2H, m), 7.41 (1H, dd, J=2.4, 9.0 Hz), 7.21-7.17 (2H, m).

Provenance & Evidence