N-methyl-2-pyrrolidone → 1,2-Dimethyl-4-(pentafluoroethyl)benzene

Participants

Reaction Conditions

Reaction Steps

Into a nitrogen purged, flame dried round bottom flask was added 4-iodo-o-xylene (15.0 g, 64.7 mmol), sodium pentafluoropropionic acid (16.8 g, 90.5 mmol), copper (I) iodide (12.3 g, 64.6 mmol) and 100 mL of anhydrous N-methylpyrrolidinone. The reaction mixture was heated at 170° C. for 16 hours, then cooled to room temperature, and run through a thick silica gel plug with hexane. The collected yellow liquids were then evaporated to dryness on a rotary evaporator, and the oil distilled at 60° C. (10−1 Torr) to collect the desired product (9.14 g, 63%) as a colorless liquid. Analysis of the product provided the following data: 1H NMR (200 MHz, CDCl3) δ=2.347 (s, 6H), 7.247 (d, J=7.8 Hz, 1H), 7.357 (s, 1H), 7.401 (s, 1H). 13C NMR (50 MHz, CDCl3) δ=19.810, 19.840, 124.013 (t, J=6.1 Hz), 127.472 (t, J=6.1 Hz), 130.158, 137.563, 141.205. GC-MS: m/z: 224 (C10H9F5).

Provenance & Evidence