Chloride → 3,5-Bis(trifluoromethyl)styrene

Participants

Reaction Conditions

Reaction Steps

A solution of 3,5-bis(trifluoromethyl)-1-bromobenzene (75 g, 0.256 mol), tetiabutylammonium chloride (71.4 g, 0.256 mol), triethylamine (71.3 mL, 0.97 mol) and palladium(II) acetate (113 mg) in acetonitrile (360 mL) was deoxygenated with a vigorous flow of nitrogen. The reaction was pressurized with ethylene (950 psi) and heated to 80° C. for 36 hours. Pentane (400 mL) was added and after 3 water washes (200 mL) the organic layer was dried over Na2SO4 and the solvent was removed in vacuo to afford 3,5-bis(trifluoromethyl)styrene as a pale yellow oil (58.2 g, 0.242 mol, 95% yield).

Provenance & Evidence