Bromotrimethylsilane → 4-(Bromomethyl)-1-methoxy-2-(3-methoxypropoxy)benzene

Participants

Reaction Steps

Trimethylsilyl bromide (97 ml) is added dropwise to a solution of 4-methoxy-3-(3-methoxypropoxy)-benzyl alcohol (111.1 g) in chloroform (1.31 liters), the reaction temperature being maintained at 10°-25° C. by cooling with ice. When the addition is complete, the mixture is stirred for a further 10 minutes at room temperature and concentrated under reduced pressure. The residue is purified by FC on silica gel (ethyl acetate/hexane 1:3) and after recrystallisation from hexane the title compound (144.5 g) is obtained in the form of a white crystalline solid: m.p. 50-51° C. Rf (ethyl acetate/hexane 1:2)=0.34.

Provenance & Evidence