1-Hexanol → {4-(4-Hexanoxy-2,3,5,6-tetrafluorophenyl)-2,3,5,6-tetrafluorophenyl}bis(triflyl)methane

HRID 459437Notes

Reaction equation

[CH2:1]([OH:7])[CH2:2][CH2:3][CH2:4][CH2:5][CH3:6].[H-].[Na+].[F:10][C:11]1[C:16]([C:17]2[C:22]([F:23])=[C:21]([F:24])[C:20]([CH:25]([S:33]([C:36]([F:39])([F:38])[F:37])(=[O:35])=[O:34])[S:26]([C:29]([F:32])([F:31])[F:30])(=[O:28])=[O:27])=[C:19]([F:40])[C:18]=2[F:41])=[C:15]([F:42])[C:14]([F:43])=[C:13](F)[C:12]=1[F:45].O.Cl>N1C=CC=CC=1>[CH2:1]([O:7][C:13]1[C:12]([F:45])=[C:11]([F:10])[C:16]([C:17]2[C:18]([F:41])=[C:19]([F:40])[C:20]([CH:25]([S:26]([C:29]([F:30])([F:31])[F:32])(=[O:27])=[O:28])[S:33]([C:36]([F:37])([F:38])[F:39])(=[O:35])=[O:34])=[C:21]([F:24])[C:22]=2[F:23])=[C:15]([F:42])[C:14]=1[F:43])[CH2:2][CH2:3][CH2:4][CH2:5][CH3:6]

Participants

Conditions

Temperature: -20 °C

Procedure

Hexanol (1.5 mL, 12 mmol) was added to a pyridine (10 mL) solution dissolved with 60% sodium hydride containing mineral oil (0.56 g, 14 mmol) at 0° C., and the resultant solution was stirred for 1 hour at room temperature. After the solution was cooled to −20° C., {4-(pentafluorophenyl)-2,3,5,6-tetrafluorophenyl}bis(triflyl)methane (1.2 g, 2 mmol) was added. The reaction solution was stirred at −20° C. for 5 hours. After the reaction, the solution was acidified with 4 M hydrochloric acid water, and was extracted with diethylether. After drying with magnesium sulfate, the solution was filtrated, and the solvent was removed under reduced pressure. The crude product was purified by sublimation (0.2 to 0.3 torr, 80° C.), and {4-(4-hexanoxy-2,3,5,6-tetrafluorophenyl)-2,3,5,6-tetrafluorophenyl}bis(triflyl)methane was obtained at 94% yield (1.27 g, 1.88 mmol).

Workup

customAfter the reaction
extractionwas extracted with diethylether
dry with materialAfter drying with magnesium sulfate
filtrationthe solution was filtrated
customthe solvent was removed under reduced pressure
customThe crude product was purified by sublimation (0.2 to 0.3 torr, 80° C.)

Sources & evidence

ORD record: ord-1079cf47f891446eb9a43f5e4399a452
Source dataset: uspto-grants-2007_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07193113B2

Reaction notes

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