Tert-Butylbenzene → (4-(Tert-butyl)phenyl)(chloromethyl)(phenyl)sulfonium triflate

반응식

[C:1]1([S:7]([CH2:9][Cl:10])=O)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[C:11]([C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1)([CH3:14])([CH3:13])[CH3:12].[F:21][C:22]([F:35])([F:34])[S:23]([O:26]S(C(F)(F)F)(=O)=O)(=[O:25])=[O:24]>C(OCC)C>[O-:26][S:23]([C:22]([F:35])([F:34])[F:21])(=[O:25])=[O:24].[C:11]([C:15]1[CH:20]=[CH:19][C:18]([S+:7]([CH2:9][Cl:10])[C:1]2[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=2)=[CH:17][CH:16]=1)([CH3:14])([CH3:13])[CH3:12]

참가 물질

실험 절차

Chloromethyl phenyl sulfoxide (200 mg, 1.29 mmol) of example 21 was dissolved in dry diethyl ether (7.5 mL) under an argon atmosphere. tert-Butyl benzene (0.191 g, 1.1 eq) was added to the previous solution and then the mixture was cooled to a temperature below −60° C. After stabilizing the temperature, trifluoromethanesulfonic anhydride (0.217 mL, 1 eq) was added slowly maintaining the same temperature. The mixture was stirred until the reaction was complete. The orange precipitated triflate salt was quickly filtered at −60° C. affording 0.487 g as red viscous oil after heating at room temperature, which was a mixture by proton NMR.