Sulfuric Acid → 3-Bromo-4-(trifluoromethoxy)benzaldehyde

Participants

Reaction Steps

To a solution of 4-trifluoromethoxybenzaldehyde (215.0 g, 1.13 mol) in a mixture of TFA (300 mL), CH2Cl2 (300 mL) and H2SO4 (150 mL) was added at room temperature N-bromosuccinimide (402.0 g, 2.26 mol) in equal portions over seven hours. The reaction mixture was stirred for four days at room temperature, poured into ice-water and extracted with CH2Cl2. The organic layer was washed with water and subsequently treated with saturated NaHCO3 (1.5 L) for two hours. The layers were separated and the organic layer further washed with water and brine, dried over MgSO4, filtered and evaporated. The residue was triturated with hexane and filtered. After evaporation of the solvent, the residue was distilled to give 3-bromo-4-trifluoromethoxybenzaldehyde (190.2 g, 81° C., 1.0 mm/Hg, 62%).

Provenance & Evidence