Trifluoroiodomethane → 1,3-Dimethyl-5-(trifluoromethyl)benzene

Participants

Reaction Steps

A solution of 5-iodo-m-xylene (2.3 g) in dimethylformamide (DMF) (30 ml) and copper bronze (0.65 g) in a stainless steel tube is cooled and treated with trifluoromethyliodide (15 g). The tube is sealed and heated at 130°-140° C. in a rocking autoclave for 6 hours. After cooling and venting, the reaction mixture is diluted with water and extracted with n-hexane (2×200 ml). The combined hexane extracts are washed with aqueous NaHCO3 and water. After drying over MgSO4, the solvent is removed under reduced pressure. The residue is subjected to chromatography over silica gel to yield purified 5-(trifluoromethyl)-m-xylene.

Provenance & Evidence