Collect. Czech. Chem. Commun. 2002, 67, 1479-1485

Convenient Preparation of 2-Phenylethyl 3,3-Difluoro-2-methylpropionate

Takashi Yamazakia,*, Tatsuro Ichigeb and Tomoya Kitazumeb

a Department of Applied Chemistry, Tokyo University of Agriculture and Technology, 2-24-16 Nakamachi, Koganei 184-8588, Japan
b Department of Bioengineering, Tokyo Institute of Technology, 4259 Nagatsuta-cho, Midori-ku, Yokohama 226-8501, Japan


The slow inverse addition of an LDA solution at -78 °C to an ester of 2-(trifluoromethyl)acrylic acid enabled efficient dehydrofluorination. Hydrogenation of the resulting difluoromethylacrylate furnished the target ester of 3,3-difluoro-2-methylpropionic acid in good overall yield.

Keywords: Fluorine; Hydrogenations; Dehydrofluorination; α,β-Unsaturated esters; Fluorinated compounds; Ab initio calculations.

References: 19 live references.