Diisopropyl Ether → 5-(p-Tolyl)thianthrenium nonafluorobutanesulfonate

HRID 1434495Notes

Reaction equation

HRID 1434495 reaction equation
[CH:1]1[C:14]2[S:13][C:12]3[C:7](=[CH:8][CH:9]=[CH:10][CH:11]=3)[S:6](=O)[C:5]=2[CH:4]=[CH:3][CH:2]=1.FC(F)(F)C(OC(=O)C(F)(F)F)=O.[F:29][C:30]([F:45])([F:44])[C:31]([F:43])([F:42])[C:32]([F:41])([F:40])[C:33]([F:39])([F:38])[S:34]([OH:37])(=[O:36])=[O:35].C(O[CH:50]([CH3:52])[CH3:51])(C)C>C1(C)C=CC=CC=1>[F:45][C:30]([F:29])([F:44])[C:31]([F:42])([F:43])[C:32]([F:40])([F:41])[C:33]([F:38])([F:39])[S:34]([O-:37])(=[O:36])=[O:35].[C:50]1([CH3:51])[CH:52]=[CH:33][C:32]([S+:6]2[C:7]3[C:12](=[CH:11][CH:10]=[CH:9][CH:8]=3)[S:13][C:14]3[CH:1]=[CH:2][CH:3]=[CH:4][C:5]2=3)=[CH:31][CH:30]=1

Participants

6

Reactant 4

HCID 7914Diisopropyl EtherHCID 9845Trifluoroacetic anhydrideHCID 67815Perfluorobutanesulfonic acidHCID 73220Thianthrene, 5-oxide

Product 1

HCID 231378245-(p-Tolyl)thianthrenium nonafluorobutanesulfonate

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

In 10 ml of toluene was dissolved 2 g of thianthrene-S-oxide and the solution was cooled with ice. Then, 2.8 ml of trifluoroacetic anhydride and 1.2 ml of nonafluorobutanesulfonic acid were added thereto, followed by stirring for one hour. Diisopropyl ether was added thereto and the supernatant solution was removed. The residue was purified by a silica gel column (chloroform/methanol=19/1) to obtain 4.4 g of 5-(p-tolyl)thianthrenium nonafluorobutanesulfonate. 1H-NMR (400 MHz, CDCl3): σ 2.34 (s, 3H), 7.08 (d, 2H), 7.22 (d, 2H), 7.78 (m, 6H), 8.65 (d, 2H).

Workup

  1. temperaturethe solution was cooled with ice
  2. customthe supernatant solution was removed
  3. customThe residue was purified by a silica gel column (chloroform/methanol=19/1)

Sources & evidence

ORD record
ord-fe3cbaa672e540b292fbcce13e566fe5
Source dataset
uspto-grants-2009_11
Patent number
US07615330B2

Reaction notes

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