4-Methoxyphenol → 2-Bromo-4-methoxyphenol

Participants

Reaction Steps

To a solution of 4-methoxyphenol (13.00 g, 104.84 mmol) in DMF (50 mL) was added bromine (5.40 mL, 104.84 mmol) at 0° C. The reaction was allowed to warm to room temperature. After stirring for 2 h the reaction was quenched with water and extracted with ethyl acetate (3×200 mL). The combined organic extracts were washed with brine and dried (Na2SO4). Removal of the solvent under reduced pressure gave 21.28 g of the crude title compound as a dark oil: 1H NMR (250 MHz, CDCl3) d 7.49 (b, 1H), 6.96 (d, 1H), 6.72-6.62 (m, 2H), 3.71 (s, 3H).

Provenance & Evidence