2-(2,2,2-Trifluoroethoxy)phenol

106854-74-4

160968-99-0

GENERAL STEPS: A 1M solution of boron tribromide (30mL, 0.03mol) in dichloromethane was slowly added dropwise to a solution of 1-methoxy-2-(2,2,2-trifluoroethoxy)benzene (4.3g, 0.02mol) in anhydrous dichloromethane (50mL) at -20°C. The reaction was quenched by addition of excess saturated aqueous sodium bicarbonate (40mL). After the reaction mixture was naturally warmed to room temperature, the reaction was quenched by the addition of excess saturated aqueous sodium bicarbonate solution (40 mL). The organic layer was separated, dried over anhydrous sodium sulfate, filtered and concentrated under reduced pressure. The crude product obtained was sufficiently pure (98% yield) to be used directly in the subsequent reaction. The product was a yellow oil (3.8 g) and UPLC/MS analysis showed a purity of 99% with a retention time of tR = 5.37 min. molecular formula C8H7F3O2, molecular weight 192.14, single isotope mass 192.04, [M+H]- m/z 191.0. 1H-NMR (300 MHz, CDCl3) δ 4.36 (q, J = 8.4 Hz, 2H, O-CH2-CF3), 6.81-7.11 (m, 4H, Ar-H), 9.72 (br.s., 1H, OH).13C-NMR (75 MHz, CDCl3) δ 56.2, 68.1, 119.2, 121.5, 122.4, 123.7, 126.4, 127.3, 136.4.