T-Butyl hypobromite

The starting material above is prepared by reacting styrene with isoamyl alcohol and then reacting that product with t-butyl hypobromite. 

An alternative procedure is most efficient when N-t-butyl amides are employed as starting materials. The iV-bromoamides are formed by halogenation with t-butyl hypobromite. Photolysis gives hydrobromide salts of iminolactones, which are easily hydrolyzed to lactones. The remote halogenation is believed to proceed by a... 

It was of interest to see if the use of tm-butyl hypobromite would provide similar opportunities for regioselectivity to those found in the case of chlorination reactions with te/t-butyl hypochlorite. The initial indications were favourable use of H zeolite X as catalyst in dichloromethane solution gave an almost quantitative yield of bromotoluenes with a para ortho ratio of 81 19 (Fig. 5) (ref. 10). 

A mixture of N-tert-butyl-4-nitrobenzamide and a soln. of acetyl hypobromite prepared from Ag-acetate and bromine in CCI4 stirred 15 min. at room temp, protected from light by aluminum foil N-bromo-N-t rt-butyl-4-nitrobenzamide. Y 99%. - F. e., also N,N-dibromination, s. T. R. Beebe and J. W. Wolfe, J. Org. Chem. 35, 2056 (1970). 

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