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Synthesis 2012(4): 605-609  
DOI: 10.1055/s-0031-1289678
PAPER
© Georg Thieme Verlag Stuttgart ˙ New York

Breakthrough in the α-Perchlorination of Acyl Chlorides

Franco Bellesiaa, Francesca D’Annab, Fulvia Fellugac, Vincenzo Frennab, Franco Ghelfi*a, Andrew F. Parsonsd, Federico Reverberi*a, Domenico Spinellie
a Dipartimento di Chimica, Università degli Studi di Modena e Reggio Emilia, Via Campi 183, 41125 Modena, Italy
Fax: +39(59)373543; e-Mail: franco.ghelfi @unimore.it;
b Dipartimento di Chimica Organica ‘E. Paternò’, Università degli Studi di Palermo, Viale delle Scienze-Parco D’Orleans II, 90128 Palermo, Italy
c Dipartimento di Scienze Chimiche e Farmaceutiche, Università degli Studi di Trieste, Via L. Giorgeri 1, 34127 Trieste, Italy
d Department of Chemistry, University of York, Heslington, York YO10 5DD, UK
e Dipartimento di Chimica ‘G. Ciamician’, Università degli Studi di Bologna, Via Selmi 2, 40126 Bologna, Italy
Further Information

Publication History

Received 25 October 2011
Publication Date:
26 January 2012 (online)

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Abstract

The preparation of α-perchloroacyl chlorides, from reaction of the corresponding unfunctionalized acyl halides with chlorine, was efficiently achieved under base-catalysis, using a tetraalkylammonium chloride as catalyst. The process is solvent-free and the procedure is easy, inexpensive, and suitable for scale-up.

Key words

acyl chlorides - halogenation - chlorine - base catalysis - 2,2-dichloroacyl chlorides

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