Hunsdiecker reaction
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The Hunsdiecker reaction (or Borodin reaction) is the organic reaction of silver salts of carboxylic acids with halogens, which gives organic halides. It is an interesting example of a halogenation reaction.
Reaction mechanism
The reaction can be written as:
- R-COOAg + Br2 → R-Br + CO2 + AgBr
If iodine is used instead of bromine, the final product will be an ester of the carboxylic acid and its corresponding alcohol. This version is called Simonini reaction.
- 2 R-COOAg + I2 → R-C(=O)O-R + CO2 + 2 AgI
Procedure
To a solution of silver carboxylate in carbon tetrachloride, elemental bromine is added.
Uses
The Hunsdiecker reaction is useful for making organic halides from silver carboxylates, such as methyl bromide from silver acetate.
