Sulfuric Acid → 4-[3-Bromo-4-(trifluoromethoxy)phenyl]pyridine

Participants

Reaction Conditions

Reaction Steps

4-[4-(Trifluoromethoxy)phenyl]pyridine (500 mg, 2.1 mmol) was suspended in water (2 ml) and conc. sulphuric acid (2 ml). The suspension was heated to 80° C. and potassium bromate (386 mg, 2.31 mmol) was added in portions over 2 hours. The reaction was stirred at 80° C. for a further 2 hours, allowed to cool to ambient temperature and then poured onto ice. The solution was basified with 4N sodium hydroxide solution, extracted with ethyl acetate (2×30 ml) and the combined organic layers were washed with water. The solution was dried over sodium sulphate and the solvent was removed in vacuo giving an oil (467 mg) which was used without further purification. 1H NMR (250 MHz, CDCl3) δ8.70 (2H, br s), 7.92-7.91 (1H, d, J=2.2 Hz), 7.62-7.58 (1H, dd, J=8.5 Hz and 2.2 Hz), and 7.47-7.41 (3H, m), m/z (ES+) 318, 320 (M+1).

Provenance & Evidence