2-CHLORO-4-HYDROXYBENZAMIDE

General procedure: The appropriate alkyl bromide (1 eq), the appropriate phenol (1.1 eq), finely ground cesium carbonate (60-80 mesh, 1.5 eq) and DMF (to 0.1-0.3M) were stirred at room temperature for two hours. The mixture was diluted with ice cold water, the resulting precipitate collected by filtration or centrifugation, washed with the minimum water and air dried to give the ether product.2-Chloro-4-hydroxy-benzonitrile (3g, 19.5mmol) was added in portions to stirred sulphuric acid (95-97%, 2OmL). The dark reddish solution was stirred periodically at room temperature for 6 days. The reaction mixture was slowly poured onto ice (300ml) with stirring and then extracted (x 3) with ethyl acetate. The combined ethyl acetate extracts were washed (water x 2, saturated brine x 1) and dried over magnesium sulphate, filtered and evaporated. The residue was purified by chromatography using a 25g isolute silica gel cartridge eluting with a gradient of 0- 100% ethyl acetate in cyclohexane to give the title compound as a solid.Yield: 0.72g, 21%1H NMR (DMSOd6): delta 6.73 (dd, 1 H), 6.81 (d, 1 H), 7.32(d, 1 H), 7.37 (s, 1 H), 7.63(s, 1 H), 10.16 (bs, 1 H)