Tetrabutylammonium Fluoride → HCID 59533946, compound

Participants

Reaction Steps

(Z)-4-(4-(Trifluoromethyl)phenoxy)-N′-hydroxybenzamidine (79 mg, 0.23 mmol) was placed under nitrogen and THF was added. Then tetrabutylammonium fluoride (67 μL, 0.23 mmol) was added dropwise and the solution was stirred at room temperature for 92 hours 40 minutes. The product was purified by column chromatography over silica gel (EtOAc/Hex 1:12) to give a white solid (9.0 mg, 12%). 1H NMR (500 MHz, CDCL3) δ(ppm): 2.66 (3H, s), 7.11-7.14 (4H, m), 7.62 (2H, d, J=8.4 Hz), 8.08 (2H, d, J=9.0 Hz). 13C NMR (125 MHz, CDCL3) δ(ppm): 12.61 (CH3), 119.0 (CH), 119.7 (CH), 122.9, 125.3, 126.0 (C, q, J=32.5 Hz), 127.5 (CH, q, J=3.8 Hz), 129.6 (CH), 158.7, 159.6, 167.9, 176.8. 19F (282 MHz, CDCL3) δ(ppm): −61.89 (3F, s). MS (FAB+): 321 (MH+). HRMS for C16H11F3N2O2 (MH+): calculated: 320.0773; found 320.0779.

Provenance & Evidence