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

HRID 1352185

Reaction equation

O.O=[Al]O[Al]=O.O=[Si]=O.F[C:11]1[C:19](F)=[C:18](F)[C:17](F)=[C:16]2[C:12]=1[CH:13]=[CH:14][NH:15]2>CC1C=CC=CC=1C>[NH:15]1[C:16]2[C:12](=[CH:11][CH:19]=[CH:18][CH:17]=2)[CH:13]=[CH:14]1

Participants

Conditions

Temperature: 100 °C

Procedure

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.

Workup

stirringDuring this time, the reaction mixture was stirred periodically for 1-2 minutes every 15-20 minutes
customAfter the first 30 minutes
customat 100° C.
temperatureto cool to room temperature
filtrationcollected by vacuum filtration
customto give a yellow (golden) solid
washThe solid was washed with toluene (3×50 mL)
customdried in vacuo for ˜15 hours
customIndole-modified clay samples were recovered in >90% yield
customstored in the drybox freezer (−35° C.) until they

Sources & evidence

ORD record: ord-94c8912e57f04c18885594bb17ef660b
Source dataset: uspto-grants-2007_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07220695B2

Linked notes

Loading…