Carbon tetrabromide → 4-Allyldimethylsilylbenzyl bromide

Participants

Reaction Steps

Reaction of 4-allyldimethylsilylbenzyl alcohol (3 Scheme 1) with triphenylphosphine and carbon tetrabromide gave 4-allyldimethylsilylbenzyl bromide (4 Scheme 13). Subsequent reaction with potassium cyanide gave 4-allyldimethylsilylphenylacetonitrile (6 Scheme 13). Under the usual coupling conditions, this was loaded to the polymer and the loading level of resin (2 Scheme 13, 0.23 mequiv/g) was determined by the mass balance of 4-bromophenylacetonitrile which was obtained from cleavage reaction of the resin with bromine.

Provenance & Evidence