Bromomethyl 4-methoxyphenyl ketone → 1-(2-Bromo-1,1-diethoxyethyl)-4-methoxybenzene

Participants

Reaction Steps

A solution of 2-bromo-1-(4'-methoxy-phenyl)-ethanone (5 g, 22 mmol), triethyl orthoformate (9 g, 61 mmol), methanesulfonic acid (0.3 g, 3.1 mmol) and ethanol (20 ml) is kept at 40° C. for 3 h. The solution is poured, under vigorous stirring, into a saturated sodium carbonate solution (0.2 l) and extracted with ethyl ether (3×50 ml). The combined organic extract is washed with a 2% sodium hydrogen carbonate solution. Evaporation of the solvent in vacuo leaves an oil, which is crystallized from methanol to give 2-bromo-1,1-diethoxy-1-(4'-methoxy-phenyl)-ethane (5 g, 16 mmol, yield: 73%) as analytically pure product.

Provenance & Evidence