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Synthesis 1992; 1992(6): 541-542
DOI: 10.1055/s-1992-26158
short paper
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The Vilsmeier Reaction: A New Synthetic Method for 5-(Chloromethyl)-2-furaldehyde

Komla Sanda* , Luc Rigal, Michel Delmas, Antoine Gaset
  • *Laboratoire de Chimie des Agroressources, Ecole Nationale Supérieure de Chimie (INPT), 118, route de Narbonne, F-31077 Toulouse Cedex, France
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Publication Date:
17 September 2002 (online)

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Phosphorus or sulfur chlorides were screened for the chlorination of 5-(hydroxymethyl)-2-furaldehyde (1) to 5-(chloromethyl)-2-furaldehyde (2), with dimethylformamide or N-methylpyrrolidone as solvents. Preparative scale experiments were carried out with suitable phosphorus oxychloride, sulfuryl chloride or methanesulfonyl chloride in the presence of dimethylformamide to give 5-(chloromethyl)-2-furaldehyde in good yields (77 to 83%).