154386-86-4Relevant articles and documents
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Bennetau,Rajarison,Dunogues
, p. 1179 - 1188 (2007/10/02)
A new method for the meta acylation of anisole and its para-methyl or fluoro derivatives, is described. Addition of two trimethysilyl groups in the 2 and 5 positions (relative to the methoxy group), followed by hydrolysis affords the corresponding 5-trimethylsilyl-3-cyclohexenones. Electrophilic substitution of the silyl group using RCOC1/2AlCl3 at low temperature provides, after final aromatisation promoted by Pd/C or CuBr2/LiBr, the expected meta acylated products. This mode of meta functionalization has been successfully applied to an original synthesis of ketoprofen starting from anisole.