Synthesis and iodination of methyl 4-tri-n-butylstannylbenzoate, p-(methoxycarbonyl)phenylmercuric chloride and p-(methoxycarbonyl)phenylboronic acid

Synthesis of methyl 4-tri-n-butylstannylbenzoate (1) was accomplished by reaction of methyl 4-bromobenzoate with hexabutylditin and palladium catalyst. Transmetallation of 1 with mercuric acetate yielded the corresponding arylmercuric acetate 4 which was readily converted to aryl mercuric halides 2a and 2b. Reaction of arylmercuric bromide 2b with diborane or catecholborane produced arylboronic acid 3 in high yield. Iodinations of 1. 2a and 3 were studied using N-chlorosuccinimide/NaI at the 10% and 100% stoichiometric amounts of NaI with Na125I added to monitor the course of the reaction.