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Preparation

The chlorides are the most useful and easiest to prepare of all the possible acyl halides.

Preparation of an acid chloride from the carboxylic acid with thionyl chloride

Click here to recall the mechanism of this reaction.

Fluorides

Acyl chlorides and anhydrides are the starting materials to obtain acyl fluorides, extremely reactive and quite dangerous to handle.

Preparation of acid fluorides with HF from acid chlorides or from anhydrides at −10 °C

Bromides

Acyl bromides are obtained by addition-elimination of phosphorus tribromide on a carboxylic acid.

Preparation of acid bromides with PBr₃

Iodides

Acyl iodides are obtained by reaction of iodine and red phosphorus (PI3 formed in situ) with a carboxylic acid.

Preparation of acid iodides with I₂ and red phosphorus