Pyridine → 5-Cyclopropyl-2-methylphenyl trifluoromethanesulfonate

Participants

Reaction Steps

To a solution of the crude product (1.73 g) and pyridine (1.21 mL, 15.0 mmol) in DCM (15 mL), Tf2O (2.17 mL, 12.8 mmol) was added at 0° C. under nitrogen. The mixture was allowed to stir for 1 h. The reaction was monitored by TLC (25% EtOAc/heptane). The mixture was diluted with brine and DCM. The organic layer was separated and concentrated. The residue was purified by flash column chromatography on 40 g silica gel (with 15 g pre-column of silica gel; eluent: heptane/EtOAc=100:0 to 85:15) to give 5-cyclopropyl-2-methylphenyl trifluoromethanesulfonate. 1H NMR (400 MHz, CDCl3) δ ppm 7.16 (d, J=7.87 Hz, 1 H), 6.96 (dd, J=1.64, 7.87 Hz, 1 H), 6.92 (d, J=1.64 Hz, 1 H), 2.32 (s, 3 H), 1.85-1.92 (m, 1 H), 0.97-1.01 (m, 2 H), 0.65-0.69 (m, 2 H).

Provenance & Evidence