1,2-dimethyl-4-(1,1,2,2,2-pentafluoroethyl)benzene synthesis

Yield:1257243-30-3 63%

Reaction Conditions:

copper(l) iodide in 1-methyl-pyrrolidin-2-one at 170; for 16 h;Inert atmosphere;

Steps:

21

Example 21 - Synthesis of 6,13-Bis(3,3,4,4,5,5,6,6,7,7,8,8,9,9,10,10,10-heptadecafluoro- decyldiisopropylsilylethvnyl)-2-pentafluoroethylpentacene Synthesis of 1,2-Dimethyl-4-pentafluoroethylbenzeneInto 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 ' Torr) to collect the desired product (9.14 g, 63%) as a colorless liquid. Analysis of the product provided the following data: ¹H ΝMR (200 MHz, CDCl₃) δ = 2.347 (s, 6H), 7.247 (d, J= 7.8 Hz, IH), 7.357 (s, IH), 7.401 (s, IH). ¹³C ΝMR (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 (Ci₀H₉F₅).

References:

WO2010/138807,2010,A1 Location in patent:Page/Page column 52