Isopropyl iodide → Isopropyl 2-formyl-6-(trifluoromethyl)benzoate

Participants

Reaction Steps

To a solution of (±)-3-hydroxy-7-(trifluoromethyl)isobenzofuran-1(3H)-one (2.2 g, 10.1 mmol) in 20 mL of DMF was added potassium carbonate (2.8 g, 20.2 mmol) followed by 2-iodopropane (1.11 mL, 11.1 mmol). The resulting mixture was allowed to stir at ambient temperature for 18 h. The reaction was diluted with 1N HCl to pH ˜4 and extracted with EtOAc. The organics were washed with 1N HCl, sat'd aq NaHCO3 and brine, dried (MgSO4), filtered through a pad of silica gel and concentrated in vacuo to afford 2.3 g (87%) of the title compound which was used without purification. 1H NMR (CDCl3): δ 10.08 (s, 1H), 8.12 (d, 1H, J=7.7 Hz), 7.95 (d, 1H, J=8.2 Hz), 7.73 (t, 1H, J=7.7 Hz), 5.44-5.36 (m, 1H), 1.40 (d, 1H, J=6.6 Hz).

Provenance & Evidence