3,3,3-Trifluoropropene → (E)-2-Fluoro-4-(3,3,3-trifluoroprop-1-enyl)benzoic acid

Participants

Reaction Conditions

Reaction Steps

A mixture of methyl-2-fluoro-4-bromobenzoate (5.0 g, 0.021 mol), tri-o-tolylphosphine (1.31 g, 0.00429 mol), tetra-N-butylammonium bromide (2.08 g, 0.00644 mol), potassium acetate (4.2 g, 0.043 mol), 3,3,3-trifluoroprop-1-ene (20 g, 0.2 mol), palladium acetate (0.24 g, 0.0011 mol) was sealed in a Parr instrument and stirred at 180° C. for 96 h. After cooling, the reaction mixture was filtered through Celite® and the filtrate was partitioned bewteen EtOAc and 1 N aq. HCl. The organic layer was separated and washed with brine, dried (Na2SO4) and concentrated. The residue was chromatographed with hexane-EtOAc(5% AcOH) (0 to 60%) to give the product as a white solid. LC-MS: t=2.98 min, m/z=233.2 (M−1).

Provenance & Evidence