The Synthesis of (4-Ethenylphenyl)diphenylmethanol

An improved and general synthesis of monomers for incorporating trityl linker groups into polystyrene synthesis supports

“…19a However, the nucleophile used was an aryl lithium and such a strongly nucleophilic species readily initiates anionic polymerization of styrene molecules and makes this method low yielding and unreliable. 20 Therefore we chose to examine the addition of the relatively less nucleophilic styrene Grignard reagent, prepared simply from 4bromostyrene and magnesium, 25 to a series of benzophenones (Scheme 1).…”

“…19b Later, Rimmer et al reported that the first synthesis of 1a was not readily reproducible due to anionic polymerisation of the starting material, and that an inverse addition procedure (4-bromostyrene added to t-BuLi) afforded acceptable and reproducible yields of 1a. 20 Most recently, Janda et al have reported the only other method for the preparation of 1a which involves a 4 step synthetic sequence starting with 4-vinylbenzyl alcohol. 21 While these reported syntheses do produce the desired product, they are less than optimal, especially when considering the reported difficulty in reproducing the results, the costs and hazards associated with using t-BuLi and potassium, and the length of the most recent synthesis.…”