1,2-Dichloroethane → 2-Bromo-1-(2-chloroethoxy)-4-methoxybenzene

Participants

Reaction Steps

To a solution of 2-bromo-4-methoxyphenol (20.00 g, 98.04 mmol) in 1,2-dichloroethane (50.00 mL, 0.63 mol) was added sodium hydroxide (12.00 g, 0.29 mol) and benzyltriethylammonium chloride (3.00 g) in water (150 mL). The mixture was stirred at reflux for 24 h and extracted with ethyl acetate (3×150 mL). The combined organic extracts were washed with brine and dried (Na2SO4). After removing the solvent under reduced pressure, flash chromatography (1:1 diethyl ether/hexane) of the residue gave 14.20 g (66% over two steps) of the title compound as a yellow oil: 1H NMR (250 MHz, CDCl3) d 7.09 (d, 1 H), 6.82-6.72 (m, 2 H), 4.27 (t, 2 H), 3.75 (t, 3 H), 3.71 (s, 3 H).

Provenance & Evidence