3,3,3-Trifluoropropene → HCID 57804190, compound

Participants

Reaction Conditions

Reaction Steps

A mixture of 4-bromo-2-methylbenzoic acid (25 g, 0.12 mol), tri-o-tolylphosphine (7.1 g, 0.023 mol), tetra-N-butylammonium chloride (9.7 g, 0.035 mol), potassium acetate (22.8 g, 0.232 mol), 3,3,3-trifluoroprop-1-ene (89 g, 0.93 mol), palladium acetate (1.3 g, 0.0058 mol) and N,N-dimethylacetamide (150 mL, 1.6 mol) was sealed in a Parr instrument and stirred at 180° C. for 120 h. After cooling, the reaction mixture was filtered through Celite® and the filtrate was partitioned between EtOAc and 1N HCl (pH 2-3). The organic layer was separated and washed with brine, dried (Na2SO4) and concentrated under vacuum. The residue was purified by column chromatography on silica gel to give a crude product (which contained a small amount of the correspnding (Z)-isomer).

Provenance & Evidence