The Hell-Volhard-Zelinsky reaction makes it possible to halogenate the a-position of carboxylic acids. Phosphorus-catalyzed bromine is used as the reagent. Phosphorus in the presence of bromine generates phosphorus tribromide, which is actually the compound that acts as a catalyst.

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The Hell-Volhard-Zelinsky mechanism occurs in four stages.
 
Stage 1. Formation of the alkanoyl bromide
 
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Stage 2. Enolization of the alkanoyl halide
 
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Stage 3. Halogenation of the position a
 
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Stage 4. Exchange
 
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