Bromine → o-Cresol, 4-bromo-alpha,alpha,alpha-trifluoro-

Participants

Reaction Conditions

Reaction Steps

A round-bottom flask with stirbar was charged with 2-(trifluoromethyl)phenol (1.7 g, 10.49 mmol) in 10 mL CH2Cl2 was cooled to 0° C. Bromine (0.540 ml, 10.49 mmol) in 2 mL CH2Cl2 was added dropwise. The reaction mixture was stirred at 0° C. for 1 hour, then allowed to warm to ambient temperature over 1 hour. Aqueous NaHSO3 solution was added, and the mixture extracted with CH2Cl2. The organic phase was washed with aqueous NaHCO3 and brine, dried (MgSO4), filtered, and concentrated. The residues were purified by flash chromatography eluting with 100% CH2Cl2, to afford the title compound. 1H NMR (300 MHz, dimethylsulfoxide-d6) δ ppm 10.90 (s, 1H), 7.63 (m, 1H), 6.98 (d, 1H).

Provenance & Evidence