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Reactivity of the 3-halo-2-amino derivatives of benzothiophene 1a-c and 2 with several ketone enolates 3-5 have been studied under photostimulated SRN1 reaction conditions.The normal substitution product 6 only was obtained in low yields using potassioacetophenone 3 as the enolate ion and 2-(tert-butoxycarbonylamino)-3-chlorobenzothiophene (1a) and 2-(tert-butoxycarbonylamino)-3-iodobenzothiophene (1c) as substrates.In all reactions the main product was the corresponding dehalogenated substrate 7a-b, thus indicating that reduction of the substrate strongly competes with the desired substitution reaction.
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Reference:
Benzothiophene – Wikipedia,
Benzothiophene | C8H6S – PubChem