15181-11-0

62938-08-3

15181-11-0

General procedure for the synthesis of 3,5-di-tert-butyltoluene from 3,5-di-tert-butylbenzyl bromide: To a Schlenk flask was added an appropriate amount of complex 6 (0.05 mmol, 5.0 mol%) and the corresponding bromoaromatic (1.0 mmol). The flask was subjected to nitrogen displacement and vacuum cycling. Tetrahydrofuran (THF, 2.0 mL) and diethyl ether solution of tert-butylmagnesium chloride (0.75 mL, 1.5 mmol, 2.0 M in diethyl ether) were subsequently added. The flask was sealed and heated at 70 °C for 24 h or stirred at room temperature. After completion of the reaction, the mixture was cooled and the reaction was quenched by the addition of ammonium chloride (NH4Cl) solution. The mixture was extracted with dichloromethane and the organic layer was dried over anhydrous sodium sulfate (Na2SO4). N-dodecane was added as an internal standard and an aliquot was analyzed by gas chromatography-mass spectrometry (GC-MS). The structure of the coupling product was confirmed by GC-MS and nuclear magnetic resonance (NMR) analysis. The analytical data of the products were in agreement with the literature reports.