Abstract
A facile and highly efficient method for the bromomethylation of thiols, using paraformaldehyde and HBr/AcOH, has been developed, which advantageously minimizes the generation of highly toxic byproducts. The preparation of 22 structurally diverse α-bromomethyl sulfides illustrates the chemo-tolerant applicability while bromo-lithium exchange and functionalization sequences, free radical reductions, and additions of the title compounds demonstrate their synthetic utility.
Highlights
A facile and highly efficient method for the bromomethylation of thiols, using paraformaldehyde and HBr/ AcOH, has been developed, which advantageously minimizes the generation of highly toxic byproducts
Halomethylation of thiols provides synthetically valuable chloromethylated intermediates, which are typically prepared by condensation with bromochloromethane in basic media,[3] or with HCl and a formaldehyde source.[4]
Other methods for the generation of bromomethylated thiol derivatives consist of replacing hydrogen bromide gas with concentrated aqueous hydrobromic acid, along with a formaldehyde source,[7] or by using dibromomethane[8] in basic media.[9]
Summary
A facile and highly efficient method for the bromomethylation of thiols, using paraformaldehyde and HBr/ AcOH, has been developed, which advantageously minimizes the generation of highly toxic byproducts. Other methods for the generation of bromomethylated thiol derivatives consist of replacing hydrogen bromide gas with concentrated aqueous hydrobromic acid, along with a formaldehyde source (usually paraformaldehyde),[7] or by using dibromomethane[8] in basic media.[9] Two or three-step procedures consisting of hydroxymethylation followed by substitution have been developed.[10] A desilylative rearrangement of a-TMS sul des has been used for the generation of bromomethylsul des.[11]
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