2,6-Lutidine → 1,1'-(2,7-Naphthalenediyl) bis(1,1,1-trifluoromethanesulfonate)

Participants

Reaction Conditions

Reaction Steps

A mixture of 2,7-dihydroxynaphthalene (3.00 g, 18.73 mmol), DMAP (0.42 g, 3.75 mmol) and 2,6-lutidine (4.41 g, 41.18 mmol) was suspended in anhydrous DCM (30 ml) and anhydrous THF (30 ml) in the presence of molecular sieves under an Ar2 atmosphere at −78° C. Tf2O (11.10 g, 39.33 mmol) was added dropwise to this stirred mixture over 15 minutes and the reaction was stirred at −78° C. for 2 hours, then for 5 hours at 0° C. After that time, the reaction was carefully neutralised with saturated aqueous NaHCO3 solution (70 ml), extracted with DMC (6×120 ml), dried (MgSO4), filtered and the solvent removed in vacuo. The orange oil thus obtained was purified by flash column chromatography (petroleum ether:EtOAc, 95:5) to give compound 1 as a white solid (4.94 g, 62%); Rf 0.27 [5% EtOAc in petroleum ether]; mp 60-62° C.; δH (CDCl3, 400 MHz) 7.92 (2H, d, J=9.2 Hz, 2×ArH), 7.73 (2H, d, J=2.4 Hz, 2×ArH), 7.40 (2H, dd, J1=8.8 Hz, J2=2.4 Hz, 2×ArH); δC (CDCl3, 100 MHz) 148.26 (2×Ar—C), 133.62 (Ar—C), 131.27 (Ar—C), 130.80 (2×Ar—CH), 121.13 (2×Ar—CH), 119.48 (2×Ar—CH), 118.77 (2×CF3); HRMS m/z calc. C12H6F6O2S2Na [M+Na]+446.9408. found [M+Na]+446.9424; anal.CHN calcd. C12H6F6O2S2 C, 34.0%; H, 1.4%. found C, 34.2%; H, 1.2%. Spectroscopic data are in accordance with those reported in literature (Yao et al., 1998).

Provenance & Evidence