The reaction of aromatic amines with benzyltrimethylammonium dichloroiodate(1—) in dichloromethane–methanol in the presence of calcium carbonate powder for several hours at room temperature gave selectively iodosubstituted aromatic amines in good yields.
The reaction of phenols with benzyltrimethylammonium tribromide in dichloromethane-methanol for 1 h at room temperature gave polybromophenols in good yields.
The reaction of phenols with benzyltrimethylammonium dichloroiodate(1–) in dichloromethane-methanol in the presence of CaCO3 or NaHCO3 for several hours at room temperature gave iodophenols in good yields.
Orange crystalline tetrabutylammonium tribromide was prepared using a simple method. The reaction of acetyl derivatives with an equimolar amount of the tribromide in dichloromethane–methanol at room temperature gave bromoacetyl derivatives in fairly good yields.
The reaction of arenes with benzyltrimethylammonium tribromide or benzyltrimethylammonium dichloroiodate in acetic acid in the presence of ZnCl2 at room temperature or at 70 °C gave bromo- or iodo-substituted arenes in good yield, respectively.
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