REVIEW Carboxyl groups can be protected as tribromoethyl esters, e.g. by reaction of the acid chloride in the presence of N,N-dimethylaniline. The group is readily cleaved with Zn/AcOH (1) (cf. 2,2,2-Trichloroethanol, L08163). The group has also been exploited in the activation of carboxylic acids for amidation with amines, by reductive cleavage of the tribromoethyl ester with a P(III) reagent, preferably Hexamethylphosphorous triamide, A12571, and triethylamine. In an analogous esterification method with alcohols, tributylphosphine - DMAP was the preferred system (2).
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