Hydrochloric Acid → HCID 57671757, compound

Participants

Reaction Steps

3-Methoxyphenol (2.0 ml, 18.2 mmol) was dissolved in dry DMF (50 ml). Sodium iodide (3.3 g, 21.9 mmol) and chloramine-T (5.0 g, 21.9 mmol) was added to the mixture and the reaction was stirred at room temperature for one hour. The reaction mixture was diluted with water (150 ml), acidified with 5% hydrochloric acid solution and extracted with ethyl acetate (2×100 ml). The organic layer was washed with 5% sodium thiosulphate solution (200 ml) and dried over sodium sulphate. The product was purified by flash chromatography on silica gel twice (first with dichloromethane, then with 20% ethyl acetate in petroleum ether). The yield was 0.82 g (18%). 1H NMR (CDCl3, 500 MHz): δ 7.52 (1H, d, J=8.5 Hz), 6.63 (1H, d, J=3.0 Hz), 6.37 (1H, dd, J=8.5 Hz, 3.0 Hz), 5.27 (1H, s), 3.81 (3H, s).

Provenance & Evidence