Trifluoromethanesulfonic acid → Phenyl[2-(trimethylsilyl)phenyl]iodanium trifluoromethanesulfonate

HRID 545648Notes

Reaction equation

C(O)(=O)C.C(O)(=O)C.[I:9][C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1.[OH:16][S:17]([C:20]([F:23])([F:22])[F:21])(=[O:19])=[O:18].[CH3:24][Si:25]([CH3:37])([CH3:36])[C:26]1[CH:31]=[CH:30][CH:29]=[CH:28][C:27]=1[Si](C)(C)C>C(Cl)Cl>[O-:19][S:17]([C:20]([F:23])([F:22])[F:21])(=[O:18])=[O:16].[C:10]1([I+:9][C:27]2[CH:28]=[CH:29][CH:30]=[CH:31][C:26]=2[Si:25]([CH3:37])([CH3:36])[CH3:24])[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1

Participants

Conditions

Temperature: 0 °C

Procedure

Iodobenzene diacetate (9.66 g, 30 mmol) was dissolved in CH2Cl2 (60 mL) with stirring and the solution chilled to 0° C. Triflic acid (5.1 mL, 58 mmol) was added dropwise to the solution and the reaction mixture was stirred for 2 h. A solution of 1,2-bis(trimethylsilyl)benzene (6.67 g, 30 mmol) in CH2Cl2 (10 mL) was added at 0° C. and the reaction was allowed to stir at room temperature for 2 h. Concentration of the reaction mixture gave crystals which were triturated in ether and collected by filtration to yield white crystals (9.82 g, 65.14%). 1H NMR (400 MHz, CDCl3) δ 8.11-7.47 (m, 9H, ArH), 0.42 (s, 9H, CH3); 13C NMR (400 MHz, CDCl3): δ 139.0, 138.4, 133.3, 133.2, 132.4, 132.3, 132.1, 109.6, 0.1.

Workup

stirringthe reaction mixture was stirred for 2 h
stirringto stir at room temperature for 2 h
customConcentration of the reaction mixture gave crystals which
customwere triturated in ether
filtrationcollected by filtration

Sources & evidence

ORD record: ord-0eae312ec01d4622a1c84dc0541fdb71
Source dataset: uspto-grants-2011_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07935782B2

Reaction notes

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