Categories: C-Cl Bond Formation >
Synthesis of acyl chlorides
Recent Literature
The conversion of carboxylic acids to their corresponding acid chlorides occurs
rapidly in the presence of a tertiary amine base and 3,3-dichlorocyclopropenes via
aromatic cation-activated nucleophilic acyl substitution. The effect of
cyclopropene substituents on the rate of conversion is examined. Conditions were
developed for the preparation of acid sensitive acid chlorides.
D. J. Hardee, L. Kovalchuke, T. H. Lambert, J. Am. Chem. Soc., 2010,
132, 5002-5003.
The reaction of tert-butyl esters with SOCl2 at room
temperature provides acid chlorides in very good unpurified yields, whereas benzyl, methyl,
ethyl, and isopropyl esters are essentially unreactive.
J. A. Greenberg, T. Sammakia, J. Org. Chem.,
2017, 82, 3245-3251.
Using an efficient visible-light photocatalysis-based method, a mixture of an
aldehyde, tert-butyl hydrogen peroxide, and N-chlorosuccinimide
afforded an acid chloride in the presence of Ru(bpy)3Cl2
as photocatalyst. A subsequent reaction with an amine provided the corresponding
amide.
N. Iqbal, E. J. Cho, J. Org. Chem.,
2016,
81, 1905-1911.