Trifluoroacetic acid → 2-(3-Fluorophenyl)chroman-6-ol

Participants

Reaction Steps

Triethylsilane (960 μl) was added slowly into a solution of 2-(3-fluorophenyl)chroman-4,6-diol (195 mg) in dichloromethane (4 ml). Trifluoroacetic acid (1.9 ml) was then added dropwise into a reaction mixture and it was stirred at room temperature for 5 hours. The reaction mixture was poured on ice-water and extracted with dichloromethane. The residue was evaporated under reduced pressure with toluene to obtain 2-(3-fluorophenyl)chroman-6-ol. 1H NMR (400 MHz, d6-DMSO) δ: 8.78 (s, 1H), 7.43 (m, 1H), 7.28-7.25 (m, 2H), 7.14 (m, 1H), 6.66 (d, 1H, J 8.5 Hz) 6.52 (dd, 1H, J 8.5, 2.7 Hz), 6.49 (d, 1H, J 2.7 Hz), 5.03 (dd, 1H, J 9.9, 2.1 Hz), 2.86 (m, 1H), 2.63 (m, 1H), 2.13 (m, 1H), 1.93 (m, 1H).

Provenance & Evidence