N-Hydroxyphthalimide → N-(3-Trifluoromethylphenoxy)phthalimide

Participants

Reaction Steps

3-Trifluoromethylphenylboronic acid (380 mg, 2.0 mmol) was subjected to the representative coupling procedure with N-hydroxyphthalimide (NHP) as outlined above (method 1). Flash chromatographic purification over silica (40% EtOAc in hexanes) afforded 10 as a white solid (270 mg, 88%). 1H-NMR (500 MHz, CDCl3) δ 7.34-7.38 (m, 1H), 7.40-7.45 (m, 2H), 7.47 (m, J=0.9, 8.1 Hz, 1H), 7.82-7.87 (m, 2H), 7.92-7.97 (m, 2H); 13C-NMR (125 MHz, CDCl3) δ 111.6, 117.8, 118.1, 121.4, 122.3, 124.2, 128.8, 130.5, 132.2, 135.1, 159.0, 162.8; LC-MS 309 m/z [MH]+, C15H9F3NO3 requires 309.

Provenance & Evidence