Thiophenol → HCID 21794508, compound

Participants

Reaction Steps

Reaction of 3-bromo-4-methylbenzoic acid 1 with thiophenol and cuprous oxide in quinoline at 180° C produces 3-phenylthio-4-methylbenzoic acid 5 in 95-96% yield. Generation of the dianion of 5 is ccomplished by sequential treatment with sodium ydride and then lithium diisopropylamide in a olvent mixture of tetrahydrofuran and 1,3-dimethylmidazolidinone at -20° C. Carboxylation at -15° with carbon dioxide at a pressure of one atmosphere produces the diacid 6 in 90% yield.

Provenance & Evidence