1H-Indole, 4,5,6,7-tetrafluoro- → Indole

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In the drybox, to a 250 ml round bottom flask was added the TEAL-treated Benclay (10.390 g, as described in 1-2) and 100 mL of anhydrous o-xylene. To the stirred slurry was added an o-xylene solution of 4,5,6,7-tetrafluoroindole (1.891 g, 0.010 mole). After stirring for 15 minutes, the stirring was stopped and the reaction mixture was heated to 100° C. During this time, the reaction mixture was stirred periodically for 1-2 minutes every 15-20 minutes. After the first 30 minutes at 100° C., the color of the solution turns from colorless to golden yellow. The reaction mixture was allowed to cool to room temperature and collected by vacuum filtration to give a yellow (golden) solid and a pale yellow solution. The solid was washed with toluene (3×50 mL) and dried in vacuo for ˜15 hours. Indole-modified clay samples were recovered in >90% yield and stored in the drybox freezer (−35° C.) until they were to be used.

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