Bromine → 2-Bromo-4-(trifluoromethoxy)phenol

Participants

Reaction Steps

A solution of 1.78 g (10.0 mmol) of 4-trifluoromethoxyphenol in 5 mL of CH2Cl2 at 0° C. was treated with a solution of 2.20 g (14.0 mmol) of bromine in 5 mL of CH2Cl2. The cooling bath was removed and the resulting mixture was stirred at rt for 20 h. The reaction quenched with 5% aqueous Na2S2O3 and the resulting mixture was partitioned between 150 mL of ether and 150 mL of H2O. The layers were separated; the organic layer was dried over MgSO4 and concentrated in vacuo. Flash chromatography on 125 g of silica gel using 9:1 v/v hexanes/CH2Cl2 as the eluant afforded 1.45 g (56%) of the title compound as an oil. 1H NMR (500 MHz, CDCl3): δ 5.50 (s, 1H), 7.02 (d, J=9.0, 1H), 7.12 (dd, J=9.0, 2.0, 1H), 7.37 (d, J=2.0, 1H).

Provenance & Evidence