Uses
2-(2-Bromoethyl)-2-methyl-1,3-dioxolane is a methyl vinyl ketone equivalent; alkylating agents for attaching a 3-ketobutyl group to various nucleophiles;
the derived organometallic reagents attach this group to electrophilic centers such as carbonyl groups; major
use in the synthesis of monoprotected 1,4-, 1,5-, and 1,6-diketones and related 1,n-difunctional compounds.
Preparation
Preparative Methods of 2-(2-Bromoethyl)-2-methyl-1,3-dioxolane: addition of methyl vinyl ketone to a two-phase mixture of benzene and
conc aq HX, followed by drying of the benzene phase, addition of ethylene glycol, and removal of water with
a Dean-Stark trap.
storage
2-(2-Bromoethyl)-2-methyl-1,3-dioxolane stored at <=0 °C. even purified samples contain some β-halo ketone which slowly loses
HX, catalyzing further decomposition.
