Chloromethyl Methyl Ether → 2-Bromo-1-methoxymethoxy-4-nitrobenzene

Participants

Reaction Conditions

Reaction Steps

4.2 g (140 mmol) of a sodium hydride dispersion (55% in oil) are added portion-wise at 0° C. to a solution of 15.3 g 2-bromo-4-nitrophenol (70 mmol) in 250 ml tetrahydrofuran. Subsequently the reaction mixture is stirred for 50 minutes at 0° C. and then mixed with 1.83 g of chloromethyl-methyl ether (19.4 mmol). The mixture is stirred for an additional hour at 0° C. and then poured into ice, extracted with ethyl acetate and the organic phase is washed with a saturated aqueous salt solution, dried over Na2SO4, filtered and concentrated. The residue so obtained is concentrated over silica gel with petroleum ether/ethyl acetate (9:1). 15.8 g (80% theoretical yield) of 2-bromo-1-methoxymethoxy-4-nitrobenzene are obtained.

Provenance & Evidence