We developed a mild aromatic halogenation
reaction using a combination
of N-halosuccinimide and PhSSiMe3 or PhSSPh.
Less reactive aromatic compounds, such as methyl 4-methoxybenzoate,
were brominated with PhSSiMe3 or PhSSPh and N-bromosuccinimide in high yields. No reaction was observed in the
absence of PhSSiMe3 or PhSSPh. This method is also applicable
to chlorination reactions using N-chlorosuccinimide
and PhSSPh.
We describe the dehydroxymethylbromination of alkoxybenzyl alcohol by using a hypervalent iodine reagent and lithium bromide in F3CCH2OH at room temperature. Selective monobromination or dibromination was possible by adjusting the molar ratios of hypervalent iodine reagent and lithium bromide.
A novel transformation reaction of methylene acetals, using a combination of trimethyl(phenylthio)silane (PhSTMS) and N-bromosuccinimide (NBS) under mild reaction conditions, is described. Various methylene acetals were converted to their corresponding bromoformates in good to high yields. Under the given conditions, the reaction proceeded via a radical pathway. Further transformation of bromoformates to their corresponding epoxides was achieved by treatment with NaOMe.
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