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Synthesis 2012(4): 527-531  
DOI: 10.1055/s-0031-1289623
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© Georg Thieme Verlag Stuttgart ˙ New York

An Environmentally Friendly Synthesis of Michler’s Ketone Analogues in Water

Valerii Z. Shirinian*a, Alexey A. Shimkina, Dmitry V. Lonshakova, Artur K. Mailyanb, Andrey G. Lvova, Michail M. Krayushkina
a N. D. Zelinsky Institute of Organic Chemistry, Russian Academy of Sciences, 47, Leninsky prosp., 119991 Moscow, Russian Federation
Fax: +7(499)1355328; e-Mail: shir@ioc.ac.ru;
b A. N. Nesmeyanov Institute of Organoelement Compounds, Russian Academy of Sciences, 28, Vavilova St., 119991 Moscow, Russian Federation
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Publication History

Received 26 September 2011
Publication Date:
24 November 2011 (online)

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Abstract

An environmentally friendly method for the synthesis of a series of novel, unsymmetrical Michler’s ketone analogues, [4-(dialkylamino)phenyl](aryl)methanones, via nucleophilic aromatic substitution of (fluorophenyl)(aryl)methanones with various amines in water­ is described. The reaction products are formed in high yields and additional purification is not required. The aqueous solvent and unreacted amines can be recycled.

Key words

Michler’s ketone - nucleophilic substitution - environmentally friendly - secondary amines - water

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