Trimethylsilylacetylene → HCID 68286487, compound

Participants

Reaction Steps

In any or all of the above embodiments, converting the 3,5-methoxybenzoic acid to the (E)-5-(2-halo-3-iodoallyl)-1,3-phenylene bis(2,2-dimethylpropanoate) may include (1) reducing the 3,5-methoxybenzoic acid to produce 3,5-dimethoxybenzyl alcohol, (2) brominating the 3,5-dimethoxybenzyl alcohol to produce 3,5-dimethoxybenzyl bromide, (3) reacting the 3,5-dimethoxybenzyl bromide with ethynyl trimethylsilane to produce (3-(3,5-dimethoxyphenyl)prop-1-ynyl)trimethylsilane, (4) desilylating the (3-(3,5-dimethoxyphenyl)prop-1-ynyl)trimethylsilane to produce 1,3-dimethoxy-5-(prop-2-ynyl)benzene, (5) adding protecting groups to the 1,3-dimethoxy-5-(prop-2-ynyl)benzene to produce 5-(prop-2-ynyl)-1,3-phenylene bis(2,2-dimethylpropanoate), wherein the protecting groups are pivaloyl groups added by reacting the 1,3-dimethoxy-5-(prop-2-ynyl)benzene with boron tribromide and then with pivaloyl chloride, and (6) halogenating the 5-(prop-2-ynyl)-1,3-phenylene bis(2,2-dimethylpropanoate) to produce (E)-5-(2-halo-3-iodoallyl)-1,3-phenylene bis(2,2-dimethylpropanoate), wherein the 2-halo corresponds to R4.

Provenance & Evidence