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

Participants

Reaction Conditions

Reaction Steps

4-(Trifluoromethoxy)benzonitrile (5.57 g, 29.8 mmol) was added to 50% aqueous sulfuric acid (60 ml) and the mixture was warmed to 80° C. Potassium bromate (5.97 g, 35.7 mmol) was added in portions over 2 hours and the mixture was stirred at 80° C. for a further 2 hours. The mixture was cooled to room temperature and poured into water (200 ml). The mixture was extracted with ethyl acetate (3×200 ml) and the combined organic layers were dried (MgSO4) and evaporated under reduced pressure to give the title compound as an orange oil (6.0 g) which contained 4-trifluoromethoxy)benzonitrile (ca. 30%) as determined by 1H NMR. 1H NMR (250 MHz, CDCl3) δ 7.97 (1H, d, J=2.0 Hz), 7.68 (1H, dd, J=8.5, 2.0 Hz), and 7.42 (1H, dq, J=8.5, 1.5 Hz).

Provenance & Evidence