Methyl Ethyl Ketone → 1,3-Dibromo-2-(2-chloroethoxy)-5-fluorobenzene

Participants

Reaction Steps

A mixture of 2,6-dibromo-4-fluoro-phenol (55 g, 0.20 mol), potassium carbonate (60 g, 0.43 mol), 1-bromo-2-chloroethane (32.5 g, 0.23 mol) and 2-butanone (500 ml) was heated to reflux for 2 hours and allowed to cool to ambient temperature. The solids were filtered and the solvent was removed under vacuum to afford an oil. The oil was dissolved in diethyl ether (300 ml) and washed with water, dried over anhydrous magnesium sulfate, charcoalized, and filtered through silica gel to afford 65.9 g (97.2%) of product as an oil; MS EI m/e 330/332/334/336 (M+); 1H NMR (CDCl3) δ3.89 (2H, t, J=6.1 Hz), 4.23 (2H, t, J=6.1 Hz), 7.28 (2H, d, J=7.5 Hz).

Provenance & Evidence